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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Nomenclature_and_etymology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature_and_etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Nomenclature and etymology</span> </div> </a> <ul id="toc-Nomenclature_and_etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structure_and_bonding" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Structure and bonding</span> </div> </a> <button aria-controls="toc-Structure_and_bonding-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Structure and bonding subsection</span> </button> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> <li id="toc-Classes_of_ketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Classes_of_ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Classes of ketones</span> </div> </a> <ul id="toc-Classes_of_ketones-sublist" class="vector-toc-list"> <li id="toc-Diketones" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Diketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.1</span> <span>Diketones</span> </div> </a> <ul id="toc-Diketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Unsaturated_ketones" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Unsaturated_ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.2</span> <span>Unsaturated ketones</span> </div> </a> <ul id="toc-Unsaturated_ketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclic_ketones" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cyclic_ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3</span> <span>Cyclic ketones</span> </div> </a> <ul id="toc-Cyclic_ketones-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Characterization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Characterization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Characterization</span> </div> </a> <button aria-controls="toc-Characterization-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Characterization subsection</span> </button> <ul id="toc-Characterization-sublist" class="vector-toc-list"> <li id="toc-Spectroscopy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Spectroscopy</span> </div> </a> <ul id="toc-Spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Qualitative_organic_tests" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Qualitative_organic_tests"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Qualitative organic tests</span> </div> </a> <ul id="toc-Qualitative_organic_tests-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Keto-enol_tautomerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Keto-enol_tautomerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Keto-enol tautomerization</span> </div> </a> <ul id="toc-Keto-enol_tautomerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid/base_properties_of_ketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid/base_properties_of_ketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Acid/base properties of ketones</span> </div> </a> <ul id="toc-Acid/base_properties_of_ketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Nucleophilic additions</span> </div> </a> <ul id="toc-Nucleophilic_additions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Other reactions</span> </div> </a> <ul id="toc-Other_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Ketone</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 72 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-72" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">72 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Ketoon" title="Ketoon – Afrikaans" lang="af" hreflang="af" data-title="Ketoon" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%8A%D8%AA%D9%88%D9%86" title="كيتون – Arabic" lang="ar" hreflang="ar" data-title="كيتون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Ketonlar" title="Ketonlar – Azerbaijani" lang="az" hreflang="az" data-title="Ketonlar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Ketone" title="Ketone – Minnan" lang="nan" hreflang="nan" data-title="Ketone" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D1%8B" title="Кетоны – Belarusian" lang="be" hreflang="be" data-title="Кетоны" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D1%8B" title="Кетоны – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Кетоны" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Ketone" title="Ketone – Central Bikol" lang="bcl" hreflang="bcl" data-title="Ketone" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD" title="Кетон – Bulgarian" lang="bg" hreflang="bg" data-title="Кетон" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Keton" title="Keton – Bosnian" lang="bs" hreflang="bs" data-title="Keton" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cetona" title="Cetona – Catalan" lang="ca" hreflang="ca" data-title="Cetona" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ketony" title="Ketony – Czech" lang="cs" hreflang="cs" data-title="Ketony" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ceton" title="Ceton – Welsh" lang="cy" hreflang="cy" data-title="Ceton" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Keton" title="Keton – Danish" lang="da" hreflang="da" data-title="Keton" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ketone" title="Ketone – German" lang="de" hreflang="de" data-title="Ketone" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Ketoonid" title="Ketoonid – Estonian" lang="et" hreflang="et" data-title="Ketoonid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B5%CF%84%CF%8C%CE%BD%CE%B5%CF%82" title="Κετόνες – Greek" lang="el" hreflang="el" data-title="Κετόνες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cetona_(qu%C3%ADmica)" title="Cetona (química) – Spanish" lang="es" hreflang="es" data-title="Cetona (química)" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Ketono" title="Ketono – Esperanto" lang="eo" hreflang="eo" data-title="Ketono" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zetona" title="Zetona – Basque" lang="eu" hreflang="eu" data-title="Zetona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%AA%D9%88%D9%86" title="کتون – Persian" lang="fa" hreflang="fa" data-title="کتون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Keton" title="Keton – Faroese" lang="fo" hreflang="fo" data-title="Keton" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/C%C3%A9tone" title="Cétone – French" lang="fr" hreflang="fr" data-title="Cétone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/C%C3%A9at%C3%B3n" title="Céatón – Irish" lang="ga" hreflang="ga" data-title="Céatón" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cetona" title="Cetona – Galician" lang="gl" hreflang="gl" data-title="Cetona" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BC%80%ED%86%A4" title="케톤 – Korean" lang="ko" hreflang="ko" data-title="케톤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A5%D5%BF%D5%B8%D5%B6%D5%B6%D5%A5%D6%80" title="Կետոններ – Armenian" lang="hy" hreflang="hy" data-title="Կետոններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%80%E0%A4%9F%E0%A5%8B%E0%A4%A8" title="कीटोन – Hindi" lang="hi" hreflang="hi" data-title="कीटोन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Keton" title="Keton – Croatian" lang="hr" hreflang="hr" data-title="Keton" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Keton" title="Keton – Indonesian" lang="id" hreflang="id" data-title="Keton" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Chetoni" title="Chetoni – Italian" lang="it" hreflang="it" data-title="Chetoni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%98%D7%95%D7%9F" title="קטון – Hebrew" lang="he" hreflang="he" data-title="קטון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%99%E1%83%94%E1%83%A2%E1%83%9D%E1%83%9C%E1%83%98" title="კეტონი – Georgian" lang="ka" hreflang="ka" data-title="კეტონი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D0%B4%D0%B0%D1%80" title="Кетондар – Kazakh" lang="kk" hreflang="kk" data-title="Кетондар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Ketoni" title="Ketoni – Swahili" lang="sw" hreflang="sw" data-title="Ketoni" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Ket%C3%B2n" title="Ketòn – Haitian Creole" lang="ht" hreflang="ht" data-title="Ketòn" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D0%B4%D0%BE%D1%80" title="Кетондор – Kyrgyz" lang="ky" hreflang="ky" data-title="Кетондор" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Ketone" title="Ketone – Latin" lang="la" hreflang="la" data-title="Ketone" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Ketoni" title="Ketoni – Latvian" lang="lv" hreflang="lv" data-title="Ketoni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Ketonai" title="Ketonai – Lithuanian" lang="lt" hreflang="lt" data-title="Ketonai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Keton" title="Keton – Hungarian" lang="hu" hreflang="hu" data-title="Keton" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD" title="Кетон – Macedonian" lang="mk" hreflang="mk" data-title="Кетон" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Keton" title="Keton – Malay" lang="ms" hreflang="ms" data-title="Keton" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Keton" title="Keton – Dutch" lang="nl" hreflang="nl" data-title="Keton" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B1%E3%83%88%E3%83%B3" title="ケトン – Japanese" lang="ja" hreflang="ja" data-title="ケトン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Keton" title="Keton – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Keton" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Cetona" title="Cetona – Occitan" lang="oc" hreflang="oc" data-title="Cetona" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Keetoonii" title="Keetoonii – Oromo" lang="om" hreflang="om" data-title="Keetoonii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%95%E0%A9%80%E0%A8%9F%E0%A9%8B%E0%A8%A8" title="ਕੀਟੋਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਕੀਟੋਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DA%A9%DB%8C%D9%B9%D9%88%D9%86" title="کیٹون – Western Punjabi" lang="pnb" hreflang="pnb" data-title="کیٹون" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ketony" title="Ketony – Polish" lang="pl" hreflang="pl" data-title="Ketony" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Cetona" title="Cetona – Portuguese" lang="pt" hreflang="pt" data-title="Cetona" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Ceton%C4%83" title="Cetonă – Romanian" lang="ro" hreflang="ro" data-title="Cetonă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D1%8B" title="Кетоны – Russian" lang="ru" hreflang="ru" data-title="Кетоны" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%9A%E0%B7%93%E0%B6%A7%E0%B7%9D%E0%B6%B1" title="කීටෝන – Sinhala" lang="si" hreflang="si" data-title="කීටෝන" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ketone" title="Ketone – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ketone" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Ket%C3%B3n" title="Ketón – Slovak" lang="sk" hreflang="sk" data-title="Ketón" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Keton" title="Keton – Slovenian" lang="sl" hreflang="sl" data-title="Keton" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%A9%DB%8C%D8%AA%DB%86%D9%86" title="کیتۆن – Central Kurdish" lang="ckb" hreflang="ckb" data-title="کیتۆن" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD" title="Кетон – Serbian" lang="sr" hreflang="sr" data-title="Кетон" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Keton" title="Keton – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Keton" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ketonit" title="Ketonit – Finnish" lang="fi" hreflang="fi" data-title="Ketonit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Keton" title="Keton – Swedish" lang="sv" hreflang="sv" data-title="Keton" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%80%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="கீட்டோன் – Tamil" lang="ta" hreflang="ta" data-title="கீட்டோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%B5%E0%B9%82%E0%B8%97%E0%B8%99" title="คีโทน – Thai" lang="th" hreflang="th" data-title="คีโทน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Keton" title="Keton – Turkish" lang="tr" hreflang="tr" data-title="Keton" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BD%D0%B8" title="Кетони – Ukrainian" lang="uk" hreflang="uk" data-title="Кетони" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Keton" title="Keton – Vietnamese" lang="vi" hreflang="vi" data-title="Keton" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%85%AE" title="酮 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="酮" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Ketone" title="Ketone – Waray" lang="war" hreflang="war" data-title="Ketone" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%85%AE" title="酮 – Wu" lang="wuu" hreflang="wuu" data-title="酮" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%85%AE" title="酮 – Cantonese" lang="yue" hreflang="yue" data-title="酮" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%85%AE" title="酮 – Chinese" lang="zh" hreflang="zh" data-title="酮" 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<div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compounds of the form >C=O</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:154px;max-width:154px"><div class="trow"><div class="tsingle" style="width:152px;max-width:152px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Aceton.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Aceton.svg/150px-Aceton.svg.png" decoding="async" width="150" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Aceton.svg/225px-Aceton.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Aceton.svg/300px-Aceton.svg.png 2x" data-file-width="138" data-file-height="82" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="width:152px;max-width:152px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Acetone-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/150px-Acetone-3D-balls.png" decoding="async" width="150" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/225px-Acetone-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/300px-Acetone-3D-balls.png 2x" data-file-width="1100" data-file-height="860" /></a></span></div><div class="thumbcaption"><a href="/wiki/Acetone" title="Acetone">Acetone</a>, the simplest ketone</div></div></div></div></div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>ketone</b> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'t' in 'tie'">t</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the structure <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−C(=O)−R'</span>, where R and R' can be a variety of <a href="/wiki/Carbon" title="Carbon">carbon</a>-containing <a href="/wiki/Substituent" title="Substituent">substituents</a>. Ketones contain a <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)−</span> (a carbon-oxygen <a href="/wiki/Double_bond" title="Double bond">double bond</a> C=O). The simplest ketone is <a href="/wiki/Acetone" title="Acetone">acetone</a> (where R and R' is <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>), with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CO</span>. Many ketones are of great importance in biology and industry. Examples include many <a href="/wiki/Sugar" title="Sugar">sugars</a> (<a href="/wiki/Ketose" title="Ketose">ketoses</a>), many <a href="/wiki/Steroids" class="mw-redirect" title="Steroids">steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>), and the <a href="/wiki/Solvent" title="Solvent">solvent</a> <a href="/wiki/Acetone" title="Acetone">acetone</a>.<sup id="cite_ref-raymond2010_1-0" class="reference"><a href="#cite_note-raymond2010-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature_and_etymology">Nomenclature and etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=1" title="Edit section: Nomenclature and etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word <i>ketone</i> is derived from <i>Aketon</i>, an old German word for <i>acetone</i>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>According to the rules of <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a>, ketone names are derived by changing the <a href="/wiki/Suffix" title="Suffix">suffix</a> <i>-ane</i> of the parent <a href="/wiki/Alkane" title="Alkane">alkane</a> to <i>-anone</i>. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example <a href="/wiki/Acetone" title="Acetone">acetone</a> and <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a>. These nonsystematic names are considered retained IUPAC names,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> although some introductory chemistry textbooks use systematic names such as "2-propanone" or "propan-2-one" for the simplest ketone (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">3</sub>−C(=<a href="/wiki/Oxygen" title="Oxygen">O</a>)−CH<sub class="template-chem2-sub">3</sub></span>) instead of "acetone". </p><p>The derived names of ketones are obtained by writing separately the names of the two <a href="/wiki/Alkyl_group" title="Alkyl group">alkyl groups</a> attached to the carbonyl group, followed by "ketone" as a separate word. Traditionally the names of the alkyl groups were written in order of increasing complexity, for example <a href="/wiki/Butanone" title="Butanone"> methyl ethyl ketone</a>. However, according to the rules of <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a>, the alkyl groups are written alphabetically, for example <a href="/wiki/Butanone" title="Butanone"> ethyl methyl ketone</a>. When the two alkyl groups are the same, the prefix "di-" is added before the name of alkyl group. The positions of other groups are indicated by <a href="/wiki/Greek_letters" class="mw-redirect" title="Greek letters">Greek letters</a>, the α-carbon being the atom adjacent to carbonyl group. </p><p>Although used infrequently, <i>oxo</i> is the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> nomenclature for the oxo group (=O) and used as prefix when the ketone does not have the highest priority. Other prefixes, however, are also used. For some common chemicals (mainly in biochemistry), <i>keto</i> refer to the ketone <a href="/wiki/Functional_group" title="Functional group">functional group</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=2" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:KetoneVarietyPack.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/KetoneVarietyPack.png/600px-KetoneVarietyPack.png" decoding="async" width="600" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/KetoneVarietyPack.png/900px-KetoneVarietyPack.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/KetoneVarietyPack.png/1200px-KetoneVarietyPack.png 2x" data-file-width="2976" data-file-height="461" /></a><figcaption>Representative ketones, from the left: <a href="/wiki/Acetone" title="Acetone">acetone</a>, a common solvent; <a href="/wiki/Oxaloacetic_acid" title="Oxaloacetic acid">oxaloacetate</a>, an intermediate in the <a href="/wiki/Krebs_Cycle" class="mw-redirect" title="Krebs Cycle">metabolism of sugars</a>; <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a> in its (mono) enol form (the enol highlighted in blue); <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>, precursor to <a href="/wiki/Nylon" title="Nylon">nylon</a>; <a href="/wiki/Muscone" title="Muscone">muscone</a>, an animal scent; and <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>, an antibiotic</figcaption></figure> <p>The ketone carbon is often described as <a href="/wiki/Orbital_hybridisation#sp2" title="Orbital hybridisation">sp<sup>2</sup> hybridized</a>, a description that includes both their electronic and molecular structure. Ketones are <a href="/wiki/Trigonal_planar" class="mw-redirect" title="Trigonal planar">trigonal planar</a> around the ketonic carbon, with C–C–O and C–C–C bond angles of approximately 120°. Ketones differ from <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> in that the carbonyl group (C=O) is bonded to two carbons within a <a href="/wiki/Carbon_skeleton" class="mw-redirect" title="Carbon skeleton">carbon skeleton</a>. In aldehydes, the carbonyl is bonded to one carbon and one hydrogen and are located at the ends of carbon chains. Ketones are also distinct from other carbonyl-containing <a href="/wiki/Functional_group" title="Functional group">functional groups</a>, such as <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>, <a href="/wiki/Ester" title="Ester">esters</a> and <a href="/wiki/Amide" title="Amide">amides</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The carbonyl group is <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar</a> because the electronegativity of the oxygen is greater than that for carbon. Thus, ketones are <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> at oxygen and <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> at carbon. Because the carbonyl group interacts with water by <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonding</a>, ketones are typically more soluble in water than the related methylene compounds. Ketones are hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and cannot hydrogen-bond to themselves. Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are more volatile than alcohols and <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> of comparable <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weights</a>. These factors relate to the pervasiveness of ketones in perfumery and as solvents. </p> <div class="mw-heading mw-heading3"><h3 id="Classes_of_ketones">Classes of ketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=3" title="Edit section: Classes of ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketones are classified on the basis of their substituents. One broad classification subdivides ketones into symmetrical and unsymmetrical derivatives, depending on the equivalency of the two organic substituents attached to the carbonyl center. Acetone and <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>CO</span>) are symmetrical ketones. <a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>C(O)CH<sub class="template-chem2-sub">3</sub>)</span> is an unsymmetrical ketone. </p> <div class="mw-heading mw-heading4"><h4 id="Diketones">Diketones</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=4" title="Edit section: Diketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Dicarbonyl" title="Dicarbonyl">dicarbonyl</a></div> <p>Many kinds of diketones are known, some with unusual properties. The simplest is <a href="/wiki/Diacetyl" title="Diacetyl">diacetyl</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>C(O)C(O)CH<sub class="template-chem2-sub">3</sub>)</span>, once used as butter-flavoring in <a href="/wiki/Popcorn" title="Popcorn">popcorn</a>. <a href="/wiki/Acetylacetone" title="Acetylacetone">Acetylacetone</a> (pentane-2,4-dione) is virtually a misnomer (inappropriate name) because this species exists mainly as the monoenol <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH=C(OH)CH<sub class="template-chem2-sub">3</sub></span>. Its enolate is a common ligand in <a href="/wiki/Coordination_chemistry" class="mw-redirect" title="Coordination chemistry">coordination chemistry</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Unsaturated_ketones">Unsaturated ketones</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=5" title="Edit section: Unsaturated ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketones containing <a href="/wiki/Alkene" title="Alkene">alkene</a> and <a href="/wiki/Alkyne" title="Alkyne">alkyne</a> units are often called unsaturated ketones. A widely used member of this class of compounds is <a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">methyl vinyl ketone</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH=CH<sub class="template-chem2-sub">2</sub></span>, a <a href="/wiki/%CE%91,%CE%B2-Unsaturated_carbonyl_compound" title="Α,β-Unsaturated carbonyl compound">α,β-unsaturated carbonyl compound</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Cyclic_ketones">Cyclic ketones</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=6" title="Edit section: Cyclic ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many ketones are cyclic. The simplest class have the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub"><i>n</i></sub>CO</span>, where <i>n</i> varies from 2 for <a href="/wiki/Cyclopropanone" title="Cyclopropanone">cyclopropanone</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>CO</span>) to the tens. Larger derivatives exist. <a href="/wiki/Cyclohexanone" title="Cyclohexanone">Cyclohexanone</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">5</sub>CO</span>), a symmetrical cyclic ketone, is an important intermediate in the production of <a href="/wiki/Nylon" title="Nylon">nylon</a>. <a href="/wiki/Isophorone" title="Isophorone">Isophorone</a>, derived from acetone, is an unsaturated, asymmetrical ketone that is the precursor to other <a href="/wiki/Polymer" title="Polymer">polymers</a>. <a href="/wiki/Muscone" title="Muscone">Muscone</a>, 3-methylpentadecanone, is an animal <a href="/wiki/Pheromone" title="Pheromone">pheromone</a>. Another cyclic ketone is <a href="/wiki/Cyclobutanone" title="Cyclobutanone">cyclobutanone</a>, having the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>CO</span>. </p> <div class="mw-heading mw-heading2"><h2 id="Characterization">Characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=7" title="Edit section: Characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An aldehyde differs from a ketone in that it has a hydrogen atom attached to its carbonyl group, making aldehydes easier to oxidize. Ketones do not have a hydrogen atom bonded to the carbonyl group, and are therefore more resistant to oxidation. They are <a href="/wiki/Oxidized" class="mw-redirect" title="Oxidized">oxidized</a> only by powerful <a href="/wiki/Oxidizing_agents" class="mw-redirect" title="Oxidizing agents">oxidizing agents</a> which have the ability to <a href="/wiki/Bond_cleavage" title="Bond cleavage">cleave</a> carbon–carbon bonds. </p> <div class="mw-heading mw-heading3"><h3 id="Spectroscopy">Spectroscopy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=8" title="Edit section: Spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketones (and aldehydes) absorb strongly in the <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infra-red spectrum</a> near 1750 <a href="/wiki/Wavenumber" title="Wavenumber">cm<sup>−1</sup></a>, which is assigned to ν<sub>C=O</sub> ("carbonyl stretching frequency"). The energy of the peak is lower for aryl and unsaturated ketones.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Whereas <a href="/wiki/Proton_NMR" class="mw-redirect" title="Proton NMR"><sup>1</sup>H NMR</a> <a href="/wiki/Spectroscopy" title="Spectroscopy">spectroscopy</a> is generally not useful for establishing the presence of a ketone, <a href="/wiki/Carbon-13_NMR" class="mw-redirect" title="Carbon-13 NMR"><sup>13</sup>C NMR</a> spectra exhibit signals somewhat downfield of 200 <a href="/wiki/Parts-per_notation#ppm" title="Parts-per notation">ppm</a> depending on structure. Such signals are typically weak due to the absence of <a href="/wiki/Nuclear_Overhauser_effect" title="Nuclear Overhauser effect">nuclear Overhauser effects</a>. Since aldehydes resonate at similar <a href="/wiki/Chemical_shift" title="Chemical shift">chemical shifts</a>, multiple resonance experiments are employed to definitively distinguish aldehydes and ketones. </p> <div class="mw-heading mw-heading3"><h3 id="Qualitative_organic_tests">Qualitative organic tests</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=9" title="Edit section: Qualitative organic tests"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Methyl ketone" redirects here. For the specific compound, see <a href="/wiki/Acetone" title="Acetone">acetone</a>.</div> <p>Ketones give positive results in <a href="/wiki/Brady%27s_test" class="mw-redirect" title="Brady's test">Brady's test</a>, the reaction with 2,4-dinitrophenylhydrazine to give the corresponding hydrazone. Ketones may be distinguished from aldehydes by giving a negative result with <a href="/wiki/Tollens%27_reagent" title="Tollens' reagent">Tollens' reagent</a> or with <a href="/wiki/Fehling%27s_solution" title="Fehling's solution">Fehling's solution</a>. Methyl ketones give positive results for the <a href="/wiki/Iodoform_test" class="mw-redirect" title="Iodoform test">iodoform test</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Ketones also give positive results when treated with <i>m</i>-dinitrobenzene in presence of dilute sodium hydroxide to give violet coloration. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=10" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many methods exist for the preparation of ketones in industrial scale and academic laboratories. Ketones are also produced in various ways by organisms; see the section on biochemistry below. </p><p>In industry, the most important method probably involves <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a>, often with air. For example, a billion kilograms of <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a> are produced annually by aerobic oxidation of <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>. Acetone is prepared by <a href="/wiki/Cumene_process" title="Cumene process">air-oxidation of cumene</a>. </p><p>For specialized or small scale <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthetic</a> applications, ketones are often prepared by <a href="/wiki/Alcohol_oxidation#Oxidation_to_ketones" title="Alcohol oxidation">oxidation of secondary alcohols</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>CH(OH) + "O" → R<sub class="template-chem2-sub">2</sub>C=O + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Typical strong <a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">oxidants</a> (source of "O" in the above reaction) include <a href="/wiki/Potassium_permanganate" title="Potassium permanganate">potassium permanganate</a> or a <a href="/wiki/Chromium" title="Chromium">Cr(VI)</a> compound. Milder conditions make use of the <a href="/wiki/Dess%E2%80%93Martin_periodinane" title="Dess–Martin periodinane">Dess–Martin periodinane</a> or the <a href="/wiki/Swern_oxidation" title="Swern oxidation">Moffatt–Swern</a> methods. </p><p>Many other methods have been developed, examples include:<sup id="cite_ref-March_8-0" class="reference"><a href="#cite_note-March-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <ul><li>By <a href="/wiki/Geminal_halide_hydrolysis" title="Geminal halide hydrolysis">geminal halide hydrolysis</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>By <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of <a href="/wiki/Alkyne" title="Alkyne">alkynes</a>.<sup id="cite_ref-Vogel_10-0" class="reference"><a href="#cite_note-Vogel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Such processes occur via <a href="/wiki/Enol" title="Enol">enols</a> and require the presence of an acid and <a href="/wiki/Mercury(II)_sulfate" title="Mercury(II) sulfate">mercury(II) sulfate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HgSO<sub class="template-chem2-sub">4</sub></span>). Subsequent enol–keto tautomerization gives a ketone. This reaction always produces a ketone, even with a terminal alkyne, the only exception being the hydration of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>, which produces <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.</li> <li>From <a href="/wiki/Weinreb_ketone_synthesis" title="Weinreb ketone synthesis">Weinreb Amides</a> using stoichiometric organometallic reagents.</li> <li><a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aryl</a> ketones can be prepared in the <a href="/wiki/Friedel%E2%80%93Crafts_acylation" class="mw-redirect" title="Friedel–Crafts acylation">Friedel–Crafts acylation</a>,<sup id="cite_ref-Friedel_11-0" class="reference"><a href="#cite_note-Friedel-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> the related <a href="/wiki/Houben%E2%80%93Hoesch_reaction" class="mw-redirect" title="Houben–Hoesch reaction">Houben–Hoesch reaction</a>,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a>.<sup id="cite_ref-Vogel_10-1" class="reference"><a href="#cite_note-Vogel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a>, and related dihydroxylation/oxidative sequences, cleave <a href="/wiki/Alkene" title="Alkene">alkenes</a> to give aldehydes or ketones, depending on alkene substitution pattern.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li> <li>From <a href="/wiki/Peroxides" class="mw-redirect" title="Peroxides">peroxides</a> (<a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a>).</li> <li>Cyclization of <a href="/wiki/Dicarboxylic_acid" title="Dicarboxylic acid">dicarboxylic acids</a> (<a href="/wiki/Ruzicka_cyclization" class="mw-redirect" title="Ruzicka cyclization">Ruzicka cyclization</a>)</li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of salts of secondary <a href="/wiki/Nitro_compound" title="Nitro compound">nitro compounds</a> ( <a href="/wiki/Nef_reaction" title="Nef reaction">Nef reaction</a><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>)</li> <li>Alkylation of thioester with <a href="/wiki/Organozinc_compound" class="mw-redirect" title="Organozinc compound">organozinc compounds</a> (<a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a>).</li> <li>Alkylation of <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chloride</a> with <a href="/wiki/Organocadmium_compound" class="mw-redirect" title="Organocadmium compound">organocadmium compounds</a> or <a href="/wiki/Organocopper_compound" class="mw-redirect" title="Organocopper compound">organocopper compounds</a>.</li> <li>The <a href="/wiki/Dakin%E2%80%93West_reaction" title="Dakin–West reaction">Dakin–West reaction</a> provides an efficient method for preparation of certain methyl ketones from carboxylic acids.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li>Ketones can be prepared by the reaction of <a href="/wiki/Grignard_reagents" class="mw-redirect" title="Grignard reagents">Grignard reagents</a> with <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>, followed by hydrolysis.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>By <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">carboxylic anhydride</a>.</li> <li>Ketones can be prepared from haloketones in <a href="/wiki/Reductive_dehalogenation_of_halo_ketones" title="Reductive dehalogenation of halo ketones">reductive dehalogenation of halo ketones</a>.</li> <li>In <a href="/wiki/Ketonic_decarboxylation" title="Ketonic decarboxylation">ketonic decarboxylation</a> symmetrical ketones are prepared from carboxylic acids.<sup id="cite_ref-Vogel_10-2" class="reference"><a href="#cite_note-Vogel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> <a href="/wiki/Secondary_(chemistry)" title="Secondary (chemistry)">secondary</a> amides,<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon">β</a>-<a href="/wiki/Keto_acid" title="Keto acid">Keto acid</a> esters,<sup id="cite_ref-Vogel_10-3" class="reference"><a href="#cite_note-Vogel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> or β-<a href="/wiki/Diketone" class="mw-redirect" title="Diketone">diketones</a> (the <a href="/wiki/Acetoacetic_ester_synthesis" title="Acetoacetic ester synthesis">acetoacetic ester synthesis</a>).</li> <li><a href="/wiki/Pinacol_rearrangement" title="Pinacol rearrangement">Acid-catalysed rearrangement</a> of <a href="/wiki/Diol#Vicinal_diols" title="Diol">1,2-diols</a>,<sup id="cite_ref-Vogel_10-4" class="reference"><a href="#cite_note-Vogel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Criegee_oxidation" title="Criegee oxidation">Criegee oxidation</a> of the same.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=11" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Keto-enol_tautomerization">Keto-enol tautomerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=12" title="Edit section: Keto-enol tautomerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Enol" title="Enol">Enol</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Keto_enol_tautomerism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Keto_enol_tautomerism.svg/250px-Keto_enol_tautomerism.svg.png" decoding="async" width="250" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Keto_enol_tautomerism.svg/375px-Keto_enol_tautomerism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Keto_enol_tautomerism.svg/500px-Keto_enol_tautomerism.svg.png 2x" data-file-width="943" data-file-height="331" /></a><figcaption>Keto-enol tautomerism. <b>1</b> is the keto form; <b>2</b> is the enol.</figcaption></figure> <p>Ketones that have at least one <a href="/wiki/Alpha-hydrogen" class="mw-redirect" title="Alpha-hydrogen">alpha-hydrogen</a>, undergo <a href="/wiki/Keto-enol_tautomerization" class="mw-redirect" title="Keto-enol tautomerization">keto-enol tautomerization</a>; the tautomer is an <a href="/wiki/Enol" title="Enol">enol</a>. Tautomerization is <a href="/wiki/Catalyzed" class="mw-redirect" title="Catalyzed">catalyzed</a> by both acids and bases. Usually, the keto form is more stable than the enol. This equilibrium allows ketones to be prepared via the <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of <a href="/wiki/Alkyne" title="Alkyne">alkynes</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Acid/base_properties_of_ketones"><span id="Acid.2Fbase_properties_of_ketones"></span>Acid/base properties of ketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=13" title="Edit section: Acid/base properties of ketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> bonds adjacent to the carbonyl in ketones are more acidic <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> ≈ 20) than the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> bonds in alkane (p<i>K</i><sub>a</sub> ≈ 50). This difference reflects resonance stabilization of the <a href="/wiki/Enolate_ion" class="mw-redirect" title="Enolate ion">enolate ion</a> that is formed upon <a href="/wiki/Deprotonation" title="Deprotonation">deprotonation</a>. The relative acidity of the α-hydrogen is important in the enolization reactions of ketones and other carbonyl compounds. The acidity of the α-hydrogen also allows ketones and other carbonyl compounds to react as nucleophiles at that position, with either <a href="/wiki/Stoichiometric" class="mw-redirect" title="Stoichiometric">stoichiometric</a> and catalytic base. Using very strong bases like lithium diisopropylamide (LDA, p<i>K</i><sub>a</sub> of conjugate acid ~36) under non-equilibrating conditions (–78 °C, 1.1 equiv LDA in THF, ketone added to base), the less-substituted <i>kinetic</i> <i>enolate</i> is generated selectively, while conditions that allow for equilibration (higher temperature, base added to ketone, using weak or insoluble bases, e.g., <a href="/wiki/Sodium_ethoxide" title="Sodium ethoxide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>ONa</span></a> in <a href="/wiki/Ethanol" title="Ethanol"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>OH</span></a>, or <a href="/wiki/Sodium_hydride" title="Sodium hydride">NaH</a>) provides the more-substituted <i>thermodynamic enolate</i>. </p><p>Ketones are also weak bases, undergoing <a href="/wiki/Protonation" title="Protonation">protonation</a> on the carbonyl oxygen in the presence of <a href="/wiki/Br%C3%B8nsted_acid" class="mw-redirect" title="Brønsted acid">Brønsted acids</a>. Ketonium ions (i.e., protonated ketones) are strong acids, with p<i>K</i><sub>a</sub> values estimated to be somewhere between –5 and –7.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Although acids encountered in organic chemistry are seldom strong enough to fully protonate ketones, the formation of equilibrium concentrations of protonated ketones is nevertheless an important step in the mechanisms of many common organic reactions, like the formation of an acetal, for example. Acids as weak as pyridinium cation (as found in pyridinium tosylate) with a p<i>K</i><sub>a</sub> of 5.2 are able to serve as catalysts in this context, despite the highly unfavorable equilibrium constant for protonation (<i>K</i><sub>eq</sub> < 10<sup>−10</sup>). </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_additions">Nucleophilic additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=14" title="Edit section: Nucleophilic additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An important set of reactions follow from the susceptibility of the carbonyl carbon toward <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> and the tendency for the enolates to add to electrophiles. Nucleophilic additions include in approximate order of their generality:<sup id="cite_ref-March_8-1" class="reference"><a href="#cite_note-March-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <ul><li>With water (hydration) gives <a href="/wiki/Geminal_diol" title="Geminal diol">geminal diols</a>, which are usually not formed in appreciable (or observable) amounts</li> <li>With an <a href="/wiki/Acetylide" title="Acetylide">acetylide</a> to give the α-<a href="/wiki/Hydroxyalkyne" class="mw-redirect" title="Hydroxyalkyne">hydroxyalkyne</a></li> <li>With <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> or a <a href="/wiki/Primary_amine" class="mw-redirect" title="Primary amine">primary amine</a> gives an <a href="/wiki/Imine" title="Imine">imine</a></li> <li>With <a href="/wiki/Secondary_amine" class="mw-redirect" title="Secondary amine">secondary amine</a> gives an <a href="/wiki/Enamine" title="Enamine">enamine</a></li> <li>With <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard</a> and <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a> to give, after aqueous workup, a <a href="/wiki/Tertiary_alcohol" class="mw-redirect" title="Tertiary alcohol">tertiary alcohol</a></li> <li>With an alcohols or <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a> to gives the <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a> or its conjugate base. With a <a href="/wiki/Diol" title="Diol">diol</a> to the <a href="/wiki/Ketal" class="mw-redirect" title="Ketal">ketal</a>. This reaction is employed to protect ketones.</li> <li>With <a href="/wiki/Sodium_amide" title="Sodium amide">sodium amide</a> resulting in C–C bond cleavage with formation of the amide RCONH<sub>2</sub> and the alkane or arene R'H, a reaction called the Haller–Bauer reaction.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=15" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Oxidation_of_Ketone.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Oxidation_of_Ketone.jpg/500px-Oxidation_of_Ketone.jpg" decoding="async" width="500" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Oxidation_of_Ketone.jpg/750px-Oxidation_of_Ketone.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Oxidation_of_Ketone.jpg/1000px-Oxidation_of_Ketone.jpg 2x" data-file-width="1150" data-file-height="295" /></a><figcaption></figcaption></figure> <p>Ketones are cleaved by strong oxidizing agents and at elevated temperatures. Their oxidation involves carbon–carbon bond cleavage to afford a mixture of carboxylic acids having lesser number of carbon atoms than the parent ketone. </p> <div class="mw-heading mw-heading3"><h3 id="Other_reactions">Other reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=16" title="Edit section: Other reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a>, reaction with an <a href="/wiki/Electrophile" title="Electrophile">electrophile</a> gives a resonance stabilized cation</li> <li>With <a href="/wiki/Phosphonium_ylide" class="mw-redirect" title="Phosphonium ylide">phosphonium ylides</a> in the <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> to give the <a href="/wiki/Alkene" title="Alkene">alkenes</a></li> <li>With <a href="/wiki/Thiol" title="Thiol">thiols</a> to give the <a href="/wiki/Thioacetal" title="Thioacetal">thioacetal</a></li> <li>With <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> or 1-disubstituted <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of hydrazine to give <a href="/wiki/Hydrazone" title="Hydrazone">hydrazones</a>.</li> <li>With a <a href="/wiki/Metal_hydride" class="mw-redirect" title="Metal hydride">metal hydride</a> gives a metal alkoxide salt, hydrolysis of which gives the alcohol, an example of <a href="/wiki/Ketone_reduction" class="mw-redirect" title="Ketone reduction">ketone reduction</a></li> <li>With <a href="/wiki/Halogen" title="Halogen">halogens</a> to form an α-<a href="/wiki/Haloketone" class="mw-redirect" title="Haloketone">haloketone</a>, a reaction that proceeds via an <a href="/wiki/Enol" title="Enol">enol</a> (see <a href="/wiki/Haloform_reaction" title="Haloform reaction">Haloform reaction</a>)</li> <li>With <a href="/wiki/Heavy_water" title="Heavy water">heavy water</a> to give an α-<a href="/wiki/Deuterated" class="mw-redirect" title="Deuterated">deuterated</a> ketone</li> <li>Fragmentation in photochemical <a href="/wiki/Norrish_reaction" title="Norrish reaction">Norrish reaction</a></li> <li>Reaction of 1,4-aminodiketones to <a href="/wiki/Oxazoles" class="mw-redirect" title="Oxazoles">oxazoles</a> by dehydration in the <a href="/wiki/Robinson%E2%80%93Gabriel_synthesis" title="Robinson–Gabriel synthesis">Robinson–Gabriel synthesis</a></li> <li>In the case of aryl–alkyl ketones, with sulfur and an amine give amides in the <a href="/wiki/Willgerodt_reaction" class="mw-redirect" title="Willgerodt reaction">Willgerodt reaction</a></li> <li>With <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamine</a> to produce <a href="/wiki/Oxime" title="Oxime">oximes</a></li> <li>With <a href="/wiki/Reducing_agents" class="mw-redirect" title="Reducing agents">reducing agents</a> to form secondary alcohols</li> <li>With <a href="/wiki/Peroxy_acid" title="Peroxy acid">peroxy acids</a> to form <a href="/wiki/Ester" title="Ester">esters</a> in the <a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=17" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Coenzyme Q10</a> and <a href="/wiki/Polyketide" title="Polyketide">Polyketide</a></div> <p>Ketones do not appear in standard <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, nucleic acids, nor lipids. The formation of organic compounds in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a> occurs via the ketone <a href="/wiki/Ribulose-1,5-bisphosphate" class="mw-redirect" title="Ribulose-1,5-bisphosphate">ribulose-1,5-bisphosphate</a>. Many sugars are ketones, known collectively as <a href="/wiki/Ketose" title="Ketose">ketoses</a>. The best known ketose is <a href="/wiki/Fructose" title="Fructose">fructose</a>; it mostly exists as a cyclic <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a>, which masks the ketone functional group. <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a> proceeds via ketones. <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">Acetoacetate</a> is an intermediate in the <a href="/wiki/Krebs_cycle" class="mw-redirect" title="Krebs cycle">Krebs cycle</a> which releases energy from sugars and carbohydrates.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>In medicine, <a href="/wiki/Acetone" title="Acetone">acetone</a>, acetoacetate, and <a href="/wiki/Beta-hydroxybutyrate" class="mw-redirect" title="Beta-hydroxybutyrate">beta-hydroxybutyrate</a> are collectively called <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a>, generated from <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>, <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, and <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> in most <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>, including humans. Ketone bodies are elevated in the blood (<a href="/wiki/Ketosis" title="Ketosis">ketosis</a>) after fasting, including a night of sleep; in both blood and <a href="/wiki/Urine" title="Urine">urine</a> in <a href="/wiki/Starvation" title="Starvation">starvation</a>; in <a href="/wiki/Hypoglycemia" title="Hypoglycemia">hypoglycemia</a>, due to causes other than <a href="/wiki/Hyperinsulinemic_hypoglycemia" title="Hyperinsulinemic hypoglycemia">hyperinsulinism</a>; in various <a href="/wiki/Inborn_error_of_metabolism" class="mw-redirect" title="Inborn error of metabolism">inborn errors of metabolism</a>, and intentionally induced via a <a href="/wiki/Ketogenic_diet" title="Ketogenic diet">ketogenic diet</a>, and in <a href="/wiki/Ketoacidosis" title="Ketoacidosis">ketoacidosis</a> (usually due to <a href="/wiki/Diabetes" title="Diabetes">diabetes</a> mellitus). Although ketoacidosis is characteristic of decompensated or untreated <a href="/wiki/Type_1_diabetes" title="Type 1 diabetes">type 1 diabetes</a>, ketosis or even ketoacidosis can occur in <a href="/wiki/Diabetes_mellitus_type_2" class="mw-redirect" title="Diabetes mellitus type 2">type 2 diabetes</a> in some circumstances as well. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=18" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketones are produced on massive scales in industry as solvents, polymer precursors, and pharmaceuticals. In terms of scale, the most important ketones are <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Methylethyl_ketone" class="mw-redirect" title="Methylethyl ketone">methylethyl ketone</a>, and <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>.<sup id="cite_ref-Ullmann_23-0" class="reference"><a href="#cite_note-Ullmann-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> They are also common in biochemistry, but less so than in organic chemistry in general. The <a href="/wiki/Combustion" title="Combustion">combustion</a> of hydrocarbons is an uncontrolled oxidation process that gives ketones as well as many other types of compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=19" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although it is difficult to generalize on the <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> of such a broad class of compounds, simple ketones are, in general, not highly toxic. This characteristic is one reason for their popularity as solvents. Exceptions to this rule are the <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> ketones such as <a href="/wiki/Methyl_vinyl_ketone" title="Methyl vinyl ketone">methyl vinyl ketone</a> with <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> of 7 mg/kg (oral).<sup id="cite_ref-Ullmann_23-1" class="reference"><a href="#cite_note-Ullmann-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=20" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Diketone" class="mw-redirect" title="Diketone">Diketone</a></li> <li><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Triketone" title="Triketone">Triketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Ketosis" title="Ketosis">Ketosis</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-raymond2010-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-raymond2010_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFRaymond2010" class="citation book cs1">Raymond, Kenneth W. (2010). <i>General Organic and Biological Chemistry</i> (3rd ed.). Wiley. p. 297.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=General+Organic+and+Biological+Chemistry&rft.pages=297&rft.edition=3rd&rft.pub=Wiley&rft.date=2010&rft.aulast=Raymond&rft.aufirst=Kenneth+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarper" class="citation web cs1">Harper, Douglas. <a rel="nofollow" class="external text" href="https://www.etymonline.com/?term=ketone">"ketone"</a>. <i><a href="/wiki/Online_Etymology_Dictionary" title="Online Etymology Dictionary">Online Etymology Dictionary</a></i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Online+Etymology+Dictionary&rft.atitle=ketone&rft.aulast=Harper&rft.aufirst=Douglas&rft_id=https%3A%2F%2Fwww.etymonline.com%2F%3Fterm%3Dketone&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">The word "ketone" was coined in 1848 by the German chemist <a href="/wiki/Leopold_Gmelin" title="Leopold Gmelin">Leopold Gmelin</a>. See: Leopold Gmelin, ed., <i>Handbuch der organischen Chemie: Organische Chemie im Allgemeinen</i> … (Handbook of organic chemistry: Organic chemistry in general … ), 4th ed., (Heidelberg, (Germany): Karl Winter, 1848), volume 1, p. 40. From page 40: <i>"Zu diesen Syndesmiden scheinen auch diejenigen Verbindungen zu gehören, die als </i>Acetone im Allegemeinen<i> (</i>Ketone?<i>) bezeichnet werden."</i> (To these syndesmides*, those compounds also seem to belong, which are designated as <i>acetones in general</i> (<i>ketones?</i>).") [*Note: In 1844, the French chemist <a href="/wiki/Auguste_Laurent" title="Auguste Laurent">Auguste Laurent</a> suggested a new nomenclature for organic compounds. One of his new classes of compounds was "syndesmides", which were compounds formed by the combination of two or more simpler organic molecules (from the Greek σύνδεσμος (<i>syndesmos</i>, union) + <i>-ide</i> (indicating a group of related compounds)). For example, acetone could be formed by the dry distillation of metal acetates, so acetone was the syndesmide of two acetate ions. See: Laurent, Auguste (1844) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2wVQAAAAYAAJ&pg=PA1089">"Classification chimique,"</a> <i>Comptes rendus</i>, <b>19</b> : 1089–1100 ; see especially p. 1097.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">List of retained IUPAC names <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_701.htm">retained IUPAC names Link</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230709172354/http://www.acdlabs.com/iupac/nomenclature/93/r93_701.htm">Archived</a> 9 July 2023 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcMurry1992" class="citation cs2"><a href="/wiki/John_E._McMurry" title="John E. McMurry">McMurry, John E.</a> (1992), <i>Organic Chemistry</i> (3rd ed.), Belmont: Wadsworth, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-534-16218-5" title="Special:BookSources/0-534-16218-5"><bdi>0-534-16218-5</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.place=Belmont&rft.edition=3rd&rft.pub=Wadsworth&rft.date=1992&rft.isbn=0-534-16218-5&rft.aulast=McMurry&rft.aufirst=John+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith2018" class="citation journal cs1">Smith, Brian (November 2018). <a rel="nofollow" class="external text" href="https://www.spectroscopyonline.com/view/co-bond-part-viii-review">"The C=O Bond, Part VIII: Review"</a>. <i>Spectroscopy</i>. November 2018. <b>33</b>: 24–29. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240213050000/https://www.spectroscopyonline.com/view/co-bond-part-viii-review">Archived</a> from the original on 13 February 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">12 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Spectroscopy&rft.atitle=The+C%3DO+Bond%2C+Part+VIII%3A+Review&rft.volume=33&rft.pages=24-29&rft.date=2018-11&rft.aulast=Smith&rft.aufirst=Brian&rft_id=https%3A%2F%2Fwww.spectroscopyonline.com%2Fview%2Fco-bond-part-viii-review&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMendham,_J.Denney,_R._C.Barnes,_J._D.Thomas,_M._J._K.2000" class="citation cs2">Mendham, J.; Denney, R. C.; Barnes, J. D.; Thomas, M. J. K. (2000), <i>Vogel's Quantitative Chemical Analysis</i> (6th ed.), New York: Prentice Hall, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-582-22628-7" title="Special:BookSources/0-582-22628-7"><bdi>0-582-22628-7</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Vogel%27s+Quantitative+Chemical+Analysis&rft.place=New+York&rft.edition=6th&rft.pub=Prentice+Hall&rft.date=2000&rft.isbn=0-582-22628-7&rft.au=Mendham%2C+J.&rft.au=Denney%2C+R.+C.&rft.au=Barnes%2C+J.+D.&rft.au=Thomas%2C+M.+J.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-March-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarvelSperry1928" class="citation journal cs1">Marvel, C. S.; Sperry, W. M. (1928). 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"Cyclopentanone". <i>Organic Syntheses</i>. <b>5</b>: 37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.005.0037">10.15227/orgsyn.005.0037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Cyclopentanone&rft.volume=5&rft.pages=37&rft.date=1925&rft_id=info%3Adoi%2F10.15227%2Forgsyn.005.0037&rft.aulast=Thorpe&rft.aufirst=J.+F.&rft.au=Kon%2C+G.+A.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHerbstShemin1939" class="citation journal cs1">Herbst, R. M.; Shemin, D. (1939). "Phenylpyruvic acid". <i>Organic Syntheses</i>. <b>19</b>: 77. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.019.0077">10.15227/orgsyn.019.0077</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Phenylpyruvic+acid&rft.volume=19&rft.pages=77&rft.date=1939&rft_id=info%3Adoi%2F10.15227%2Forgsyn.019.0077&rft.aulast=Herbst&rft.aufirst=R.+M.&rft.au=Shemin%2C+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEvans2005" class="citation web cs1">Evans, David A. (4 November 2005). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180619071445/http://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf">"Evans pKa table"</a> <span class="cs1-format">(PDF)</span>. <i>Evans group website</i>. Archived from <a rel="nofollow" class="external text" href="http://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 19 June 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">14 June</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Evans+group+website&rft.atitle=Evans+pKa+table&rft.date=2005-11-04&rft.aulast=Evans&rft.aufirst=David+A.&rft_id=http%3A%2F%2Fevans.rc.fas.harvard.edu%2Fpdf%2Fevans_pKa_table.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith2013" class="citation book cs1">Smith, Michael B. (2013). <i>March's Advanced Organic Chemistry</i> (7th ed.). Hoboken, N.J.: Wiley. pp. 314–315. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-46259-1" title="Special:BookSources/978-0-470-46259-1"><bdi>978-0-470-46259-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=March%27s+Advanced+Organic+Chemistry&rft.place=Hoboken%2C+N.J.&rft.pages=314-315&rft.edition=7th&rft.pub=Wiley&rft.date=2013&rft.isbn=978-0-470-46259-1&rft.aulast=Smith&rft.aufirst=Michael+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070910060716/http://nagoyaren.homeip.net/chem/reactions/123.htm">Haller–Bauer Reaction</a>. homeip.net</span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text">Nelson, D. L.; Cox, M. M. (2000) <i>Lehninger, Principles of Biochemistry</i>. 3rd Ed. Worth Publishing: New York. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-57259-153-6" title="Special:BookSources/1-57259-153-6">1-57259-153-6</a>.</span> </li> <li id="cite_note-Ullmann-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_23-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSiegelEggersdorfer2000" class="citation book cs1">Siegel, Hardo; Eggersdorfer, Manfred (2000). "Ketones". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a15077">10.1002/14356007.a15077</a> (inactive 1 November 2024). <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527306732" title="Special:BookSources/9783527306732"><bdi>9783527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ketones&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a15077&rft.isbn=9783527306732&rft.aulast=Siegel&rft.aufirst=Hardo&rft.au=Eggersdorfer%2C+Manfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetone" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: DOI inactive as of November 2024 (<a href="/wiki/Category:CS1_maint:_DOI_inactive_as_of_November_2024" title="Category:CS1 maint: DOI inactive as of November 2024">link</a>)</span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketone&action=edit&section=22" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 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title="Carbon">Carbon</a>-based</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ane" title="-ane">-ane</a> (<a href="/wiki/Alkane" title="Alkane">alkane</a>)</li> <li><a href="/wiki/-ene" title="-ene">-ene</a> (<a href="/wiki/Alkene" title="Alkene">alkene</a>)</li> <li><a href="/wiki/-ine" title="-ine">-ine</a> (unsaturated <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>)</li> <li><a href="/wiki/-yne" title="-yne">-yne</a> (<a href="/wiki/Alkyne" title="Alkyne">alkyne</a>)</li> <li><a href="/wiki/Alk-" title="Alk-">alk-</a> (nonaromatic <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>)</li> <li><a href="https://en.wiktionary.org/wiki/ar-" class="extiw" title="wiktionary:ar-">ar-</a> (<a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a>)</li> <li><a href="/wiki/Cyclo-" class="mw-redirect" title="Cyclo-">cyclo-</a> (<a href="/wiki/Alicyclic_compound" title="Alicyclic compound">cyclic</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-al" title="-al">-al</a> (<a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>)</li> <li><a href="/wiki/-oate" title="-oate">-oate</a> (<a href="/wiki/Ester" title="Ester">ester</a>)</li> <li><a href="/wiki/-oic_acid" class="mw-redirect" title="-oic acid">-oic acid</a> (<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>)</li> <li><a href="/wiki/-ol" title="-ol">-ol</a> (<a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>)</li> <li><a href="/wiki/-one" title="-one">-one</a> (<a class="mw-selflink selflink">ketone</a>)</li> <li><a href="/wiki/-ose" title="-ose">-ose</a> (<a href="/wiki/Sugar" title="Sugar">sugar</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a>-based</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ine" title="-ine">-ine</a> (<a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>)</li> <li><a href="/wiki/Aza-" title="Aza-">aza-</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a> replaces <a href="/wiki/Carbon" title="Carbon">C</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thio-" title="Thio-">thio-</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a> replaces <a href="/wiki/Oxygen" title="Oxygen">O</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Counting axial atoms</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Meth-" class="mw-redirect" title="Meth-">meth-</a> (1)</li> <li><a href="/wiki/Eth-" class="mw-redirect" title="Eth-">eth-</a> (2)</li> <li><a href="/wiki/Prop-" class="mw-redirect" title="Prop-">prop-</a> (3)</li> <li><a href="/wiki/But-" class="mw-redirect" title="But-">but-</a> (4)</li> <li>(and the rest are <a href="/wiki/Numeral_prefix#Greek_series" title="Numeral prefix">ordinary Greek/Latin prefixes</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ase" title="-ase">-ase</a> (<a href="/wiki/Enzyme" title="Enzyme">enzyme</a>)</li> <li><a href="/wiki/Substituent#Nomenclature" title="Substituent">-yl</a> (<a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a>)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_aldehyde-ketone_(EC_2.2)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a 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href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.2.1:_Transketolases_and_Transaldolases" title="List of EC numbers (EC 2)">2.2.1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetolactate_synthase" title="Acetolactate synthase">Acetolactate synthase</a></li> <li><a href="/wiki/Transaldolase" title="Transaldolase">Transaldolase</a></li> <li><a href="/wiki/Transketolase" title="Transketolase">Transketolase</a></li> <li><a href="/wiki/DXP_synthase" class="mw-redirect" title="DXP synthase">DXP synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerases:_intramolecular_oxidoreductases_(EC_5.3)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Intramolecular_oxidoreductases" title="Template:Intramolecular oxidoreductases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Intramolecular_oxidoreductases" title="Template talk:Intramolecular oxidoreductases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Intramolecular_oxidoreductases" title="Special:EditPage/Template:Intramolecular oxidoreductases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerases:_intramolecular_oxidoreductases_(EC_5.3)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerases</a>: intramolecular <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.3)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.1:_Interconverting_Aldoses_and_Ketoses" title="List of EC numbers (EC 5)">5.3.1</a>: <a href="/wiki/Aldose" title="Aldose">Aldoses</a>/<a href="/wiki/Ketose" title="Ketose">Ketoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Triosephosphate_isomerase" title="Triosephosphate isomerase">Triosephosphate isomerase</a></li> <li><a href="/wiki/Ribose-5-phosphate_isomerase" title="Ribose-5-phosphate isomerase">Ribose-5-phosphate isomerase</a></li> <li><a href="/wiki/Mannose_phosphate_isomerase" title="Mannose phosphate isomerase">Mannose phosphate isomerase</a></li> <li><a href="/wiki/Xylose_isomerase" title="Xylose isomerase">Glucose isomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.2:_Interconverting_Keto-_and_Enol-Groups" title="List of EC numbers (EC 5)">5.3.2</a>: <a class="mw-selflink selflink">Keto</a>/<a href="/wiki/Enol" title="Enol">Enol</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylpyruvate_tautomerase" title="Phenylpyruvate tautomerase">Phenylpyruvate tautomerase</a></li> <li><a href="/wiki/Oxaloacetate_tautomerase" title="Oxaloacetate tautomerase">Oxaloacetate tautomerase</a></li> <li><a href="/wiki/4-Oxalocrotonate_tautomerase" title="4-Oxalocrotonate tautomerase">4-Oxalocrotonate tautomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.3:_Transposing_C.3DC_Bonds" title="List of EC numbers (EC 5)">5.3.3</a>: C = C</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Steroid_Delta-isomerase" title="Steroid Delta-isomerase">Steroid D-isomerase</a></li> <li><a href="/wiki/Isopentenyl-diphosphate_delta_isomerase" title="Isopentenyl-diphosphate delta isomerase">Isopentenyl-diphosphate delta isomerase</a></li> <li><a href="/wiki/Vinylacetyl-CoA_Delta-isomerase" title="Vinylacetyl-CoA Delta-isomerase">Vinylacetyl-CoA D-isomerase</a></li> <li><a href="/wiki/Muconolactone_Delta-isomerase" class="mw-redirect" title="Muconolactone Delta-isomerase">Muconolactone D-isomerase</a></li> <li><a href="/wiki/Cholestenol_Delta-isomerase" title="Cholestenol Delta-isomerase">Cholestenol Delta-isomerase</a> (<a href="/wiki/Emopamil_binding_protein" title="Emopamil binding protein">EBP</a>)</li> <li><a href="/wiki/Methylitaconate_Delta-isomerase" title="Methylitaconate Delta-isomerase">Methylitaconate D-isomerase</a></li> <li><a href="/wiki/Aconitate_Delta-isomerase" title="Aconitate Delta-isomerase">Aconitate Delta-isomerase</a></li> <li><a href="/wiki/Enoyl_CoA_isomerase" title="Enoyl CoA isomerase">Enoyl CoA isomerase</a></li> <li><a href="/wiki/Prostaglandin-A1_Delta-isomerase" title="Prostaglandin-A1 Delta-isomerase">Prostaglandin-A1 Delta-isomerase</a></li> <li><a href="/wiki/5-carboxymethyl-2-hydroxymuconate_Delta-isomerase" title="5-carboxymethyl-2-hydroxymuconate Delta-isomerase">5-carboxymethyl-2-hydroxymuconate D-isomerase</a></li> <li><a href="/wiki/Isopiperitenone_Delta-isomerase" title="Isopiperitenone Delta-isomerase">Isopiperitenone D-isomerase</a></li> <li><a href="/wiki/L-dopachrome_isomerase" title="L-dopachrome isomerase">L-dopachrome isomerase</a></li> <li><a href="/wiki/Polyenoic_fatty_acid_isomerase" title="Polyenoic fatty acid isomerase">Polyenoic fatty acid isomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.4:_Transposing_S-S_Bonds" title="List of EC numbers (EC 5)">5.3.4</a>: S-S</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein_disulfide-isomerase" title="Protein disulfide-isomerase">Protein disulfide-isomerase</a> (<a href="/wiki/PDIA3" title="PDIA3">PDIA3</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.99:_Other_Intramolecular_Oxidoreductases" title="List of EC numbers (EC 5)">5.3.99</a>: other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostaglandin_D2_synthase" title="Prostaglandin D2 synthase">Prostaglandin D2 synthase</a>/<a href="/wiki/Prostaglandin-D_synthase" title="Prostaglandin-D synthase">Prostaglandin-D synthase</a></li> <li><a href="/wiki/Prostaglandin_E_synthase" title="Prostaglandin E synthase">Prostaglandin E synthase</a></li> <li><a href="/wiki/Prostacyclin_synthase" title="Prostacyclin synthase">Prostacyclin synthase</a></li> <li><a href="/wiki/Thromboxane-A_synthase" title="Thromboxane-A synthase">Thromboxane-A synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a class="mw-selflink selflink">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Metabolism:_lipid_metabolism_–_ketones/cholesterol_synthesis_enzymes/steroid_metabolism" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e7dcc3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cholesterol_and_steroid_metabolism_enzymes" title="Template:Cholesterol and steroid metabolism enzymes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_metabolism_enzymes" title="Template talk:Cholesterol and steroid metabolism enzymes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_metabolism_enzymes" title="Special:EditPage/Template:Cholesterol and steroid metabolism enzymes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metabolism:_lipid_metabolism_–_ketones/cholesterol_synthesis_enzymes/steroid_metabolism" style="font-size:114%;margin:0 4em"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a>: <a href="/wiki/Lipid_metabolism" title="Lipid metabolism">lipid metabolism</a> – <a class="mw-selflink selflink">ketones</a>/<a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> synthesis <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a>/<a href="/wiki/Steroid_metabolism" class="mw-redirect" title="Steroid metabolism">steroid metabolism</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiolase" title="Thiolase">Acetyl-Coenzyme A acetyltransferase</a></li> <li><a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA synthase</a> (regulated step)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Ketogenesis" title="Ketogenesis">Ketogenesis</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-hydroxy-3-methylglutaryl-CoA_lyase" class="mw-redirect" title="3-hydroxy-3-methylglutaryl-CoA lyase">HMG-CoA lyase</a></li> <li><a href="/wiki/3-hydroxybutyrate_dehydrogenase" class="mw-redirect" title="3-hydroxybutyrate dehydrogenase">3-hydroxybutyrate dehydrogenase</a></li> <li><a href="/wiki/Thiophorase" class="mw-redirect" title="Thiophorase">Thiophorase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA reductase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mevalonate_kinase" title="Mevalonate kinase">Mevalonate kinase</a></li> <li><a href="/wiki/Phosphomevalonate_kinase" title="Phosphomevalonate kinase">Phosphomevalonate kinase</a></li> <li><a href="/wiki/Pyrophosphomevalonate_decarboxylase" class="mw-redirect" title="Pyrophosphomevalonate decarboxylase">Pyrophosphomevalonate decarboxylase</a></li> <li><a href="/wiki/Isopentenyl-diphosphate_delta_isomerase" title="Isopentenyl-diphosphate delta isomerase">Isopentenyl-diphosphate delta isomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">Geranyl-</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimethylallyltranstransferase" title="Dimethylallyltranstransferase">Dimethylallyltranstransferase</a></li> <li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl-diphosphate_farnesyltransferase" title="Farnesyl-diphosphate farnesyltransferase">Farnesyl-diphosphate farnesyltransferase</a></li> <li><a href="/wiki/Squalene_monooxygenase" title="Squalene monooxygenase">Squalene monooxygenase</a></li> <li><a href="/wiki/Lanosterol_synthase" title="Lanosterol synthase">Lanosterol synthase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a> path</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lanosterol_14%CE%B1-demethylase" class="mw-redirect" title="Lanosterol 14α-demethylase">Lanosterol 14α-demethylase</a></li> <li><a href="/wiki/Sterol-C5-desaturase-like" title="Sterol-C5-desaturase-like">Sterol-C5-desaturase-like</a></li> <li><a href="/wiki/7-Dehydrocholesterol_reductase" title="7-Dehydrocholesterol reductase">7-Dehydrocholesterol reductase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a> path</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/24-Dehydrocholesterol_reductase" title="24-Dehydrocholesterol reductase">24-Dehydrocholesterol reductase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol_7%CE%B1-hydroxylase" class="mw-redirect" title="Cholesterol 7α-hydroxylase">Cholesterol 7α-hydroxylase</a></li> <li><a href="/wiki/CYP27A1" title="CYP27A1">Sterol 27-hydroxylase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite"><a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">Steroidogenesis</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">Cholesterol side-chain cleavage</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a>:</i> <a href="/wiki/Aldosterone_synthase" title="Aldosterone synthase">18-Hydroxylase</a></li></ul> <ul><li><i><a href="/wiki/Cortisol" title="Cortisol">cortisol</a>/<a href="/wiki/Cortisone" title="Cortisone">cortisone</a>:</i> <a href="/wiki/CYP17A1" title="CYP17A1">17α-Hydroxylase</a></li> <li><a href="/wiki/11%CE%B2-Hydroxysteroid_dehydrogenase" title="11β-Hydroxysteroid dehydrogenase">11β-<abbr title="Hydroxysteroid dehydrogenase">HSD</abbr></a> <ul><li><a href="/wiki/11%CE%B2-Hydroxysteroid_dehydrogenase_type_1" title="11β-Hydroxysteroid dehydrogenase type 1">1</a></li> <li><a href="/wiki/11%CE%B2-Hydroxysteroid_dehydrogenase_type_2" class="mw-redirect" title="11β-Hydroxysteroid dehydrogenase type 2">2</a></li></ul></li></ul> <ul><li><i>both:</i> <a href="/wiki/3%CE%B2-Hydroxysteroid_dehydrogenase" title="3β-Hydroxysteroid dehydrogenase">3β-<abbr title="Hydroxysteroid dehydrogenase">HSD</abbr></a> <ul><li><a href="/wiki/HSD3B1" title="HSD3B1">1</a></li> <li><a href="/wiki/HSD3B2" title="HSD3B2">2</a></li></ul></li> <li><a href="/wiki/21-Hydroxylase" title="21-Hydroxylase">21-Hydroxylase</a></li> <li><a href="/wiki/11%CE%B2-Hydroxylase" class="mw-redirect" title="11β-Hydroxylase">11β-Hydroxylase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Androgen" title="Androgen">androgens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CYP17A1" title="CYP17A1">17α-Hydroxylase</a></li> <li><a href="/wiki/CYP17A1" title="CYP17A1">17,20-Lyase</a></li> <li><a href="/wiki/3%CE%B2-Hydroxysteroid_dehydrogenase" title="3β-Hydroxysteroid dehydrogenase">3β-<abbr title="Hydroxysteroid dehydrogenase">HSD</abbr></a></li> <li><a href="/wiki/17%CE%B2-Hydroxysteroid_dehydrogenase" title="17β-Hydroxysteroid dehydrogenase">17β-<abbr title="Hydroxysteroid dehydrogenase">HSD</abbr></a></li> <li><a href="/wiki/5-alpha_reductase" class="mw-redirect" title="5-alpha reductase">5α-Reductase</a> <ul><li><a href="/wiki/SRD5A1" title="SRD5A1">1</a></li> <li><a href="/wiki/SRD5A2" title="SRD5A2">2</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">To <a href="/wiki/Estrogen" title="Estrogen">estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aromatase" title="Aromatase">Aromatase</a></li> <li><a href="/wiki/17%CE%B2-Hydroxysteroid_dehydrogenase" title="17β-Hydroxysteroid dehydrogenase">17β-<abbr title="Hydroxysteroid dehydrogenase">HSD</abbr></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">Other/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Steroid_metabolism" class="mw-redirect" title="Steroid metabolism">Steroid metabolism</a>: <i><a href="/wiki/Sulfatase" title="Sulfatase">sulfatase</a></i> <ul><li><a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase">Steroid sulfatase</a></li></ul></li> <li><i><a href="/wiki/Sulfotransferase" title="Sulfotransferase">sulfotransferase</a></i> <ul><li><a href="/wiki/SULT1A1" title="SULT1A1">SULT1A1</a></li> <li><a href="/wiki/SULT2A1" class="mw-redirect" title="SULT2A1">SULT2A1</a></li></ul></li></ul> <ul><li><a href="/wiki/Steroidogenic_acute_regulatory_protein" title="Steroidogenic acute regulatory protein">Steroidogenic acute regulatory protein</a></li> <li><a href="/wiki/Cholesterol_total_synthesis" title="Cholesterol total synthesis">Cholesterol total synthesis</a></li> <li><a href="/wiki/Reverse_cholesterol_transport" title="Reverse cholesterol transport">Reverse cholesterol transport</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferase:_one_carbon_transferases_(EC_2.1)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:One-carbon_transferases" title="Template:One-carbon transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:One-carbon_transferases" title="Template talk:One-carbon transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:One-carbon_transferases" title="Special:EditPage/Template:One-carbon transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferase:_one_carbon_transferases_(EC_2.1)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferase</a>: one carbon transferases (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.1)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.1.1:_Methyltransferases" title="List of EC numbers (EC 2)">2.1.1</a>: <a href="/wiki/Methyltransferase" title="Methyltransferase">Methyl-</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">N-</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Histamine_N-methyltransferase" title="Histamine N-methyltransferase">Histamine N-methyltransferase</a></li> <li><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">Phenylethanolamine N-methyltransferase</a></li> <li><a href="/wiki/Amine_N-methyltransferase" title="Amine N-methyltransferase">Amine N-methyltransferase</a></li> <li><a href="/wiki/Phosphatidylethanolamine_N-methyltransferase" title="Phosphatidylethanolamine N-methyltransferase">Phosphatidylethanolamine N-methyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">O-</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylserotonin_O-methyltransferase" title="Acetylserotonin O-methyltransferase">5-hydroxyindole-O-methyltransferase</a>/<a href="/wiki/Acetylserotonin_O-methyltransferase" title="Acetylserotonin O-methyltransferase">Acetylserotonin O-methyltransferase</a></li> <li><a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase">Catechol-O-methyl transferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Betaine-homocysteine_S-methyltransferase" class="mw-redirect" title="Betaine-homocysteine S-methyltransferase">Betaine-homocysteine methyltransferase</a></li> <li><a href="/wiki/Homocysteine_methyltransferase" class="mw-redirect" title="Homocysteine methyltransferase">Homocysteine methyltransferase</a></li> <li><a href="/wiki/Methionine_synthase" title="Methionine synthase">Methionine synthase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphatidyl_ethanolamine_methyltransferase" class="mw-redirect" title="Phosphatidyl ethanolamine methyltransferase">Phosphatidyl ethanolamine methyltransferase</a></li> <li><a href="/wiki/DNMT3B" title="DNMT3B">DNMT3B</a></li> <li><a href="/wiki/Histone_methyltransferase" title="Histone methyltransferase">Histone methyltransferase</a></li> <li><a href="/wiki/Thymidylate_synthase" title="Thymidylate synthase">Thymidylate synthase</a></li> <li><a href="/wiki/DNA_methyltransferase" title="DNA methyltransferase">DNA methyltransferase</a></li> <li><a href="/wiki/Thiopurine_methyltransferase" title="Thiopurine methyltransferase">Thiopurine methyltransferase</a></li> <li><a href="/wiki/Cyclopropane-fatty-acyl-phospholipid_synthase" title="Cyclopropane-fatty-acyl-phospholipid synthase">Cyclopropane-fatty-acyl-phospholipid synthase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.1.2:_Hydroxymethyl-.2C_Formyl-_and_Related_Transferases" title="List of EC numbers (EC 2)">2.1.2</a>: <a href="/wiki/Hydroxymethyl" class="mw-redirect" title="Hydroxymethyl">Hydroxymethyl</a>-,<br /><a href="/wiki/Formyl" class="mw-redirect" title="Formyl">Formyl</a>- and Related</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydroxymethyltransferase" class="mw-redirect" title="Hydroxymethyltransferase">Hydroxymethyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Serine_hydroxymethyltransferase" title="Serine hydroxymethyltransferase">Serine hydroxymethyltransferase</a></li> <li><a href="/wiki/3-methyl-2-oxobutanoate_hydroxymethyltransferase" title="3-methyl-2-oxobutanoate hydroxymethyltransferase">3-methyl-2-oxobutanoate hydroxymethyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Formyltransferase" class="mw-redirect" title="Formyltransferase">Formyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphoribosylglycinamide_formyltransferase" title="Phosphoribosylglycinamide formyltransferase">Phosphoribosylglycinamide formyltransferase</a></li> <li><a href="/wiki/Inosine_monophosphate_synthase" title="Inosine monophosphate synthase">Inosine monophosphate synthase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glutamate_formimidoyltransferase" title="Glutamate formimidoyltransferase">Glutamate formimidoyltransferase</a></li> <li><a href="/wiki/Aminomethyltransferase" title="Aminomethyltransferase">Aminomethyltransferase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.1.3:_Carboxy-_and_Carbamoyltransferases" title="List of EC numbers (EC 2)">2.1.3</a>: <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxy</a>-<br />and <a href="/wiki/Carbamoyl" class="mw-redirect" title="Carbamoyl">Carbamoyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl-CoA_carboxytransferase" title="Methylmalonyl-CoA carboxytransferase">methylmalonyl-CoA carboxytransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Carbamoyl</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartate_carbamoyltransferase" title="Aspartate carbamoyltransferase">Aspartate carbamoyltransferase</a></li> <li><a href="/wiki/Ornithine_carbamoyltransferase" class="mw-redirect" title="Ornithine carbamoyltransferase">Ornithine carbamoyltransferase</a></li> <li><a href="/wiki/Oxamate_carbamoyltransferase" title="Oxamate carbamoyltransferase">Oxamate carbamoyltransferase</a></li> <li><a href="/wiki/Putrescine_carbamoyltransferase" title="Putrescine carbamoyltransferase">Putrescine carbamoyltransferase</a></li> <li><a href="/wiki/3-hydroxymethylcephem_carbamoyltransferase" title="3-hydroxymethylcephem carbamoyltransferase">3-hydroxymethylcephem carbamoyltransferase</a></li> <li><a href="/wiki/Lysine_carbamoyltransferase" title="Lysine carbamoyltransferase">Lysine carbamoyltransferase</a></li> <li><a href="/wiki/N-acetylornithine_carbamoyltransferase" title="N-acetylornithine carbamoyltransferase">N-acetylornithine carbamoyltransferase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.1.4:_Amidinotransferases" title="List of EC numbers (EC 2)">2.1.4</a>: <a href="/wiki/Amidine" title="Amidine">Amidine</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arginine:glycine_amidinotransferase" title="Arginine:glycine amidinotransferase">Arginine:glycine amidinotransferase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_aldehyde-ketone_(EC_2.2)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aldehyde-ketone_transferases" title="Template:Aldehyde-ketone transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aldehyde-ketone_transferases" title="Template talk:Aldehyde-ketone transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aldehyde-ketone_transferases" title="Special:EditPage/Template:Aldehyde-ketone transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_aldehyde-ketone_(EC_2.2)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>-<a class="mw-selflink selflink">ketone</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.2)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.2.1:_Transketolases_and_Transaldolases" title="List of EC numbers (EC 2)">2.2.1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetolactate_synthase" title="Acetolactate synthase">Acetolactate synthase</a></li> <li><a href="/wiki/Transaldolase" title="Transaldolase">Transaldolase</a></li> <li><a href="/wiki/Transketolase" title="Transketolase">Transketolase</a></li> <li><a href="/wiki/DXP_synthase" class="mw-redirect" title="DXP synthase">DXP synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_acyltransferases_(EC_2.3)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Acyltransferases" title="Template:Acyltransferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acyltransferases" title="Template talk:Acyltransferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acyltransferases" title="Special:EditPage/Template:Acyltransferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_acyltransferases_(EC_2.3)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Acyltransferase" title="Acyltransferase">acyltransferases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.3)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.3.1:_Transferring_groups_other_than_amino-acyl_groups" title="List of EC numbers (EC 2)">2.3.1</a>: other than amino-acyl groups</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Acetyltransferase" title="Acetyltransferase">acetyltransferases</a>:</i> <a href="/wiki/Thiolase" title="Thiolase">Acetyl-Coenzyme A acetyltransferase</a></li> <li><a href="/wiki/N-Acetylglutamate_synthase" title="N-Acetylglutamate synthase">N-Acetylglutamate synthase</a></li> <li><a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase">Choline acetyltransferase</a></li> <li><a href="/wiki/Dihydrolipoyl_transacetylase" title="Dihydrolipoyl transacetylase">Dihydrolipoyl transacetylase</a></li> <li><a href="/wiki/Acetyl-CoA_C-acyltransferase" class="mw-redirect" title="Acetyl-CoA C-acyltransferase">Acetyl-CoA C-acyltransferase</a></li> <li><a href="/wiki/Beta-galactoside_transacetylase" class="mw-redirect" title="Beta-galactoside transacetylase">Beta-galactoside transacetylase</a></li> <li><a href="/wiki/Chloramphenicol_acetyltransferase" title="Chloramphenicol acetyltransferase">Chloramphenicol acetyltransferase</a></li> <li><a href="/wiki/N-acetyltransferase" title="N-acetyltransferase">N-acetyltransferase</a> <ul><li><a href="/wiki/Serotonin_N-acetyl_transferase" class="mw-redirect" title="Serotonin N-acetyl transferase">Serotonin N-acetyl transferase</a></li> <li><a href="/wiki/HGSNAT" title="HGSNAT">HGSNAT</a></li> <li><a href="/wiki/ARD1A" class="mw-redirect" title="ARD1A">ARD1A</a></li></ul></li> <li><a href="/wiki/Histone_acetyltransferase" title="Histone acetyltransferase">Histone acetyltransferase</a> <ul><li><a href="/wiki/P300-CBP_coactivator_family" title="P300-CBP coactivator family">P300/CBP</a></li> <li><a href="/wiki/NAT2" class="mw-redirect" title="NAT2">NAT2</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Palmitoyltransferase" class="mw-redirect" title="Palmitoyltransferase">palmitoyltransferases</a>:</i> <a href="/wiki/Carnitine_O-palmitoyltransferase" title="Carnitine O-palmitoyltransferase">Carnitine O-palmitoyltransferase</a> <ul><li><a href="/wiki/Carnitine_palmitoyltransferase_I" title="Carnitine palmitoyltransferase I">CPT1</a></li> <li><a href="/wiki/Carnitine_palmitoyltransferase_II" title="Carnitine palmitoyltransferase II">CPT2</a></li></ul></li> <li><a href="/wiki/Serine_C-palmitoyltransferase" title="Serine C-palmitoyltransferase">Serine C-palmitoyltransferase</a> <ul><li><a href="/wiki/SPTLC1" title="SPTLC1">SPTLC1</a></li> <li><a href="/wiki/SPTLC2" title="SPTLC2">SPTLC2</a></li></ul></li></ul> <ul><li><i>other:</i> <a href="/wiki/Acyltransferase_like_2" title="Acyltransferase like 2">Acyltransferase like 2</a></li> <li><a href="/wiki/Aminolevulinic_acid_synthase" title="Aminolevulinic acid synthase">Aminolevulinic acid synthase</a></li> <li><a href="/wiki/Beta-ketoacyl-ACP_synthase" title="Beta-ketoacyl-ACP synthase">Beta-ketoacyl-ACP synthase</a></li> <li><a href="/wiki/Glyceronephosphate_O-acyltransferase" title="Glyceronephosphate O-acyltransferase">Glyceronephosphate O-acyltransferase</a></li> <li><a href="/wiki/Lecithin%E2%80%94cholesterol_acyltransferase" class="mw-redirect" title="Lecithin—cholesterol acyltransferase">Lecithin—cholesterol acyltransferase </a></li></ul> <ul><li><a href="/wiki/Glycerol-3-phosphate_O-acyltransferase" title="Glycerol-3-phosphate O-acyltransferase">Glycerol-3-phosphate O-acyltransferase</a></li> <li><a href="/wiki/1-acylglycerol-3-phosphate_O-acyltransferase" title="1-acylglycerol-3-phosphate O-acyltransferase">1-acylglycerol-3-phosphate O-acyltransferase</a></li> <li><a href="/wiki/2-acylglycerol-3-phosphate_O-acyltransferase" title="2-acylglycerol-3-phosphate O-acyltransferase">2-acylglycerol-3-phosphate O-acyltransferase</a></li> <li><a href="/wiki/ABHD5" title="ABHD5">ABHD5</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.3.2:_Aminoacyltransferases" title="List of EC numbers (EC 2)">2.3.2</a>: <a href="/wiki/Aminoacyltransferase" title="Aminoacyltransferase">Aminoacyltransferases</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gamma-glutamyl_transpeptidase" class="mw-redirect" title="Gamma-glutamyl transpeptidase">Gamma-glutamyl transpeptidase</a></li> <li><a href="/wiki/Peptidyl_transferase" class="mw-redirect" title="Peptidyl transferase">Peptidyl transferase</a></li> <li><a href="/wiki/Transglutaminase" title="Transglutaminase">Transglutaminase</a> <ul><li><a href="/wiki/Tissue_transglutaminase" title="Tissue transglutaminase">Tissue transglutaminase</a></li> <li><a href="/wiki/Keratinocyte_transglutaminase" title="Keratinocyte transglutaminase">Keratinocyte transglutaminase</a></li> <li><a href="/wiki/Factor_XIII" title="Factor XIII">Factor XIII</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.3.3:_Acyl_groups_converted_into_alkyl_on_transfer" title="List of EC numbers (EC 2)">2.3.3</a>: converted into alkyl on transfer</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrate_synthase" title="Citrate synthase">Citrate synthase</a></li> <li><a href="/wiki/Decylcitrate_synthase" title="Decylcitrate synthase">Decylcitrate synthase</a></li> <li><a href="/wiki/Citrate_(Re)-synthase" title="Citrate (Re)-synthase">Citrate (Re)-synthase</a></li> <li><a href="/wiki/Decylhomocitrate_synthase" title="Decylhomocitrate synthase">Decylhomocitrate synthase</a></li> <li><a href="/wiki/2-methylcitrate_synthase" title="2-methylcitrate synthase">2-methylcitrate synthase</a></li> <li><a href="/wiki/2-ethylmalate_synthase" title="2-ethylmalate synthase">2-ethylmalate synthase</a></li> <li><a href="/wiki/3-ethylmalate_synthase" title="3-ethylmalate synthase">3-ethylmalate synthase</a></li> <li><a href="/wiki/ATP_citrate_lyase" class="mw-redirect" title="ATP citrate lyase">ATP citrate lyase</a></li> <li><a href="/wiki/Malate_synthase" title="Malate synthase">Malate synthase</a></li> <li><a href="/wiki/Hydroxymethylglutaryl-CoA_synthase" title="Hydroxymethylglutaryl-CoA synthase">HMG-CoA synthase</a> <ul><li><a href="/wiki/HMGCS2" title="HMGCS2">HMGCS2</a></li></ul></li> <li><a href="/wiki/2-hydroxyglutarate_synthase" title="2-hydroxyglutarate synthase">2-hydroxyglutarate synthase</a></li> <li><a href="/wiki/3-propylmalate_synthase" title="3-propylmalate synthase">3-propylmalate synthase</a></li> <li><a href="/wiki/2-isopropylmalate_synthase" title="2-isopropylmalate synthase">2-isopropylmalate synthase</a></li> <li><a href="/wiki/Homocitrate_synthase" title="Homocitrate synthase">Homocitrate synthase</a></li> <li><a href="/wiki/Sulfoacetaldehyde_acetyltransferase" title="Sulfoacetaldehyde acetyltransferase">Sulfoacetaldehyde acetyltransferase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_glycosyltransferases_(EC_2.4)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycosyltransferases" title="Template:Glycosyltransferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycosyltransferases" title="Template talk:Glycosyltransferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycosyltransferases" title="Special:EditPage/Template:Glycosyltransferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_glycosyltransferases_(EC_2.4)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">glycosyltransferases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.4)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.4.1:_Hexosyltransferases" title="List of EC numbers (EC 2)">2.4.1</a>: <a href="/wiki/Hexosyltransferase" title="Hexosyltransferase">Hexosyl-<br />transferases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucosyltransferase" title="Glucosyltransferase">Glucosyl-</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphorylase" title="Phosphorylase">Phosphorylase</a> <ul><li><a href="/wiki/Starch_phosphorylase" title="Starch phosphorylase">Starch</a></li> <li><a href="/wiki/Glycogen_phosphorylase" title="Glycogen phosphorylase">Glycogen</a></li> <li><a href="/wiki/Cellobiose_phosphorylase" title="Cellobiose phosphorylase">Cellobiose</a></li> <li><a href="/wiki/Myophosphorylase" title="Myophosphorylase">Myo-</a></li></ul></li> <li><a href="/wiki/Glycogen_synthase" title="Glycogen synthase">Glycogen synthase</a></li> <li><a href="/wiki/Glycogen_debranching_enzyme" title="Glycogen debranching enzyme">Debranching enzyme</a></li> <li><a href="/wiki/Glycogen_branching_enzyme" title="Glycogen branching enzyme">Branching enzyme</a></li> <li><a href="/wiki/1,3-Beta-glucan_synthase" title="1,3-Beta-glucan synthase">1,3-Beta-glucan synthase</a></li> <li><a href="/wiki/Ceramide_glucosyltransferase" title="Ceramide glucosyltransferase">Ceramide glucosyltransferase</a></li> <li><a href="/wiki/N-glycosyltransferase" title="N-glycosyltransferase">N-glycosyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Galactosyltransferase" title="Galactosyltransferase">Galactosyl-</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lactose_synthase" title="Lactose synthase">Lactose synthase</a></li> <li><a href="/wiki/B-N-acetylglucosaminyl-glycopeptide_b-1,4-galactosyltransferase" title="B-N-acetylglucosaminyl-glycopeptide b-1,4-galactosyltransferase">B-N-acetylglucosaminyl-glycopeptide b-1,4-galactosyltransferase</a></li> <li><a href="/wiki/Glycoprotein-N-acetylgalactosamine_3-beta-galactosyltransferase" title="Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase">Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase</a> (<a href="/wiki/C1GALT1" title="C1GALT1">C1GALT1</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucuronosyltransferase" title="Glucuronosyltransferase">Glucuronosyl-</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/B3GAT1" title="B3GAT1">B3GAT1</a></li> <li><a href="/wiki/B3GAT2" title="B3GAT2">B3GAT2</a></li> <li><a href="/wiki/B3GAT3" title="B3GAT3">B3GAT3</a></li></ul> <ul><li><a href="/wiki/UDP_glucuronosyltransferase_1_family,_polypeptide_A1" title="UDP glucuronosyltransferase 1 family, polypeptide A1">UGT1A1</a></li> <li><a href="/wiki/UGT1A3" title="UGT1A3">UGT1A3</a></li> <li><a href="/wiki/UGT1A4" title="UGT1A4">UGT1A4</a></li> <li><a href="/wiki/UGT1A5" title="UGT1A5">UGT1A5</a></li> <li><a href="/wiki/UGT1A6" title="UGT1A6">UGT1A6</a></li> <li><a href="/wiki/UGT1A7" class="mw-redirect" title="UGT1A7">UGT1A7</a></li> <li><a href="/wiki/UGT1A8" title="UGT1A8">UGT1A8</a></li> <li><a href="/wiki/UGT1A9" title="UGT1A9">UGT1A9</a></li> <li><a href="/wiki/UGT1A10" title="UGT1A10">UGT1A10</a></li></ul> <ul><li><a href="/wiki/UGT2A1" title="UGT2A1">UGT2A1</a></li> <li><a href="/wiki/UGT2A2" title="UGT2A2">UGT2A2</a></li> <li><a href="/wiki/UGT2A3" class="mw-redirect" title="UGT2A3">UGT2A3</a></li> <li><a href="/wiki/UGT2B4" title="UGT2B4">UGT2B4</a></li> <li><a href="/wiki/UGT2B7" title="UGT2B7">UGT2B7</a></li> <li><a href="/wiki/UGT2B10" title="UGT2B10">UGT2B10</a></li> <li><a href="/wiki/UGT2B11" class="mw-redirect" title="UGT2B11">UGT2B11</a></li> <li><a href="/wiki/UGT2B15" title="UGT2B15">UGT2B15</a></li> <li><a href="/wiki/UGT2B17" title="UGT2B17">UGT2B17</a></li> <li><a href="/wiki/UGT2B28" class="mw-redirect" title="UGT2B28">UGT2B28</a></li></ul> <ul><li><a href="/wiki/Hyaluronan_synthase" title="Hyaluronan synthase">Hyaluronan synthase</a>: <a href="/wiki/HAS1" title="HAS1">HAS1</a></li> <li><a href="/wiki/HAS2" title="HAS2">HAS2</a></li> <li><a href="/wiki/HAS3" title="HAS3">HAS3</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fucosyltransferase" title="Fucosyltransferase">Fucosyl-</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/GDP-fucose_protein_O-fucosyltransferase_1" title="GDP-fucose protein O-fucosyltransferase 1">POFUT1</a></li> <li><a href="/wiki/GDP-fucose_protein_O-fucosyltransferase_2" title="GDP-fucose protein O-fucosyltransferase 2">POFUT2</a></li> <li><a href="/wiki/FUT1" title="FUT1">FUT1</a></li> <li><a href="/wiki/FUT2" title="FUT2">FUT2</a></li> <li><a href="/wiki/Fucosyltransferase_3" title="Fucosyltransferase 3">FUT3</a></li> <li><a href="/wiki/FUT4" title="FUT4">FUT4</a></li> <li><a href="/wiki/FUT5" title="FUT5">FUT5</a></li> <li><a href="/wiki/FUT6" title="FUT6">FUT6</a></li> <li><a href="/wiki/FUT7" title="FUT7">FUT7</a></li> <li><a href="/wiki/FUT8" title="FUT8">FUT8</a></li> <li><a href="/wiki/FUT9" title="FUT9">FUT9</a></li> <li><a href="/w/index.php?title=FUT10&action=edit&redlink=1" class="new" title="FUT10 (page does not exist)">FUT10</a></li> <li><a href="/w/index.php?title=FUT11&action=edit&redlink=1" class="new" title="FUT11 (page does not exist)">FUT11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mannosyltransferase" title="Mannosyltransferase">Mannosyl-</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dolichyl-phosphate-mannose-protein_mannosyltransferase" title="Dolichyl-phosphate-mannose-protein mannosyltransferase">Dolichyl-phosphate-mannose-protein mannosyltransferase</a> <ul><li><a href="/wiki/POMT1" title="POMT1">POMT1</a></li> <li><a href="/wiki/POMT2" title="POMT2">POMT2</a></li></ul></li> <li><a href="/wiki/DPM1" title="DPM1">DPM1</a></li> <li><a href="/wiki/DPM3" title="DPM3">DPM3</a></li></ul> <ul><li><a href="/wiki/ALG1" title="ALG1">ALG1</a></li> <li><a href="/wiki/ALG2" title="ALG2">ALG2</a></li> <li><a href="/wiki/ALG3" title="ALG3">ALG3</a></li> <li><a href="/wiki/ALG6" title="ALG6">ALG6</a></li> <li><a href="/wiki/ALG8" title="ALG8">ALG8</a></li> <li><a href="/wiki/ALG9" title="ALG9">ALG9</a></li> <li><a href="/wiki/ALG12" title="ALG12">ALG12</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.4.2:_Pentosyltransferases" title="List of EC numbers (EC 2)">2.4.2</a>: <a href="/wiki/Pentosyltransferase" title="Pentosyltransferase">Pentosyl-<br />transferases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Ribose" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ribose" title="Ribose">Ribose</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/NAD(%2B)%E2%80%94diphthamide_ADP-ribosyltransferase" title="NAD(+)—diphthamide ADP-ribosyltransferase">NAD<sup>+</sup>:diphthamide ADP-ribosyltransferase</a> <ul><li><a href="/wiki/Diphtheria_toxin" title="Diphtheria toxin">Diphtheria toxin</a></li> <li><a href="/wiki/Pseudomonas_exotoxin" title="Pseudomonas exotoxin">Pseudomonas exotoxin</a></li></ul></li></ul> <ul><li><a href="/wiki/NAD(P)(%2B)%E2%80%94protein-arginine_ADP-ribosyltransferase" title="NAD(P)(+)—protein-arginine ADP-ribosyltransferase">NAD(P)<sup>+</sup>:arginine ADP-ribosyltransferase</a> <ul><li><a href="/wiki/Pertussis_toxin" title="Pertussis toxin">Pertussis toxin</a></li> <li><a href="/wiki/Cholera_toxin" title="Cholera toxin">Cholera toxin</a></li></ul></li></ul> <ul><li><a href="/wiki/Poly_ADP_ribose_polymerase" class="mw-redirect" title="Poly ADP ribose polymerase">Poly ADP ribose polymerase</a></li></ul> <ul><li><a href="/wiki/Sirtuin" title="Sirtuin">Sirtuin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphoribosyltransferase" title="Phosphoribosyltransferase">Phosphoribosyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenine_phosphoribosyltransferase" title="Adenine phosphoribosyltransferase">Adenine phosphoribosyltransferase</a></li> <li><a href="/wiki/Hypoxanthine-guanine_phosphoribosyltransferase" title="Hypoxanthine-guanine phosphoribosyltransferase">Hypoxanthine-guanine phosphoribosyltransferase</a></li> <li><a href="/wiki/Uracil_phosphoribosyltransferase" title="Uracil phosphoribosyltransferase">Uracil phosphoribosyltransferase</a></li> <li><a href="/wiki/Amidophosphoribosyltransferase" title="Amidophosphoribosyltransferase">Amidophosphoribosyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Purine_nucleoside_phosphorylase" title="Purine nucleoside phosphorylase">Purine nucleoside phosphorylase</a>: <a href="/wiki/Thymidine_phosphorylase" title="Thymidine phosphorylase">Thymidine phosphorylase</a> <ul><li><a href="/wiki/ECGF1" class="mw-redirect" title="ECGF1">ECGF1</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Xylosyltransferase" title="Xylosyltransferase">Xylosyltransferase</a> <ul><li><a href="/wiki/XYLT1" title="XYLT1">XYLT1</a></li> <li><a href="/wiki/XYLT2" title="XYLT2">XYLT2</a></li></ul></li> <li><a href="/wiki/Arabinosyltransferase" title="Arabinosyltransferase">Arabinosyltransferase</a> <ul><li><a href="/wiki/Indolylacetylinositol_arabinosyltransferase" title="Indolylacetylinositol arabinosyltransferase">Indolylacetylinositol arabinosyltransferase</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.4.99:_Transferring_Other_Glycosyl_Groups" title="List of EC numbers (EC 2)">2.4.99</a>: <a href="/wiki/Sialyltransferase" title="Sialyltransferase">Sialyl<br />transferases</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-galactoside_alpha-2,6-sialyltransferase" title="Beta-galactoside alpha-2,6-sialyltransferase">Beta-galactoside alpha-2,6-sialyltransferase</a></li> <li><a href="/wiki/Monosialoganglioside_sialyltransferase" title="Monosialoganglioside sialyltransferase">Monosialoganglioside sialyltransferase</a></li> <li><a href="/wiki/ST8SIA4" title="ST8SIA4">ST8SIA4</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_alkyl_and_aryl_(EC_2.5)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alkyl_and_aryl_transferases" title="Template:Alkyl and aryl transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alkyl_and_aryl_transferases" title="Template talk:Alkyl and aryl transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alkyl_and_aryl_transferases" title="Special:EditPage/Template:Alkyl and aryl transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_alkyl_and_aryl_(EC_2.5)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Alkane" title="Alkane">alkyl</a> and <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.5)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.5:_Transferring_Alkyl_or_Aryl_Groups.2C_Other_than_Methyl_Groups" title="List of EC numbers (EC 2)">2.5.1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dimethylallyltranstransferase" title="Dimethylallyltranstransferase">Dimethylallyltranstransferase</a></li> <li><a href="/wiki/Thiaminase" title="Thiaminase">Thiaminase I</a></li> <li><a href="/wiki/Methionine_adenosyltransferase" class="mw-redirect" title="Methionine adenosyltransferase">Methionine adenosyltransferase</a></li> <li><a href="/wiki/Riboflavin_synthase" title="Riboflavin synthase">Riboflavin synthase</a></li> <li><a href="/wiki/Dihydropteroate_synthase" title="Dihydropteroate synthase">Dihydropteroate synthase</a></li> <li><a href="/wiki/Spermidine_synthase" title="Spermidine synthase">Spermidine synthase</a></li> <li><a href="/wiki/Glutathione_S-transferase" title="Glutathione S-transferase">Glutathione S-transferase</a></li> <li><a href="/wiki/Farnesyl-diphosphate_farnesyltransferase" title="Farnesyl-diphosphate farnesyltransferase">Farnesyl-diphosphate farnesyltransferase</a></li> <li><a href="/wiki/Spermine_synthase" title="Spermine synthase">Spermine synthase</a></li> <li><a href="/wiki/Alkylglycerone_phosphate_synthase" title="Alkylglycerone phosphate synthase">Alkylglycerone phosphate synthase</a></li> <li><a href="/wiki/Farnesyltransferase" title="Farnesyltransferase">Farnesyltransferase</a></li> <li><a href="/wiki/Geranylgeranyltransferase_type_1" title="Geranylgeranyltransferase type 1">Geranylgeranyltransferase type 1</a></li> <li><a href="/wiki/Porphobilinogen_deaminase" title="Porphobilinogen deaminase">Porphobilinogen deaminase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferase:_nitrogenous_groups_(EC_2.6)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nitrogenous_transferases" title="Template:Nitrogenous transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogenous_transferases" title="Template talk:Nitrogenous transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogenous_transferases" title="Special:EditPage/Template:Nitrogenous transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferase:_nitrogenous_groups_(EC_2.6)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferase</a>: <a href="/wiki/Nitrogen" title="Nitrogen">nitrogenous</a> groups (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.6)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.6.1:_Transaminases" title="List of EC numbers (EC 2)">2.6.1</a>: <a href="/wiki/Transaminase" title="Transaminase">Transaminases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartate_transaminase" title="Aspartate transaminase">Aspartate transaminase</a> <ul><li><a href="/wiki/GOT1" title="GOT1">GOT1</a></li> <li><a href="/wiki/GOT2" title="GOT2">GOT2</a></li></ul></li> <li><a href="/wiki/Alanine_transaminase" title="Alanine transaminase">Alanine transaminase</a></li> <li><a href="/wiki/4-Aminobutyrate_aminotransferase" class="mw-redirect" title="4-Aminobutyrate aminotransferase">GABA transaminase</a></li> <li><a href="/wiki/Tyrosine_aminotransferase" title="Tyrosine aminotransferase">Tyrosine aminotransferase</a></li> <li><a href="/wiki/Kynurenine%E2%80%94oxoglutarate_transaminase" title="Kynurenine—oxoglutarate transaminase">Kynurenine—oxoglutarate transaminase</a></li> <li><a href="/wiki/Ornithine_aminotransferase" title="Ornithine aminotransferase">Ornithine aminotransferase</a></li> <li><a href="/wiki/Branched-chain_amino_acid_aminotransferase" title="Branched-chain amino acid aminotransferase">Branched-chain amino acid aminotransferase</a></li> <li><a href="/wiki/Alanine%E2%80%94glyoxylate_transaminase" title="Alanine—glyoxylate transaminase">Alanine—glyoxylate transaminase</a> <ul><li><a href="/wiki/AGXT" title="AGXT">AGXT</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.6.3:_Oximinotransferases" title="List of EC numbers (EC 2)">2.6.3</a>: Oximinotransferases</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oximinotransferase" title="Oximinotransferase">Oximinotransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.6.99:_Transferring_Other_Nitrogenous_Groups" title="List of EC numbers (EC 2)">2.6.99</a>: Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pyridoxine_5%27-phosphate_synthase" title="Pyridoxine 5'-phosphate synthase">Pyridoxine 5'-phosphate synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_phosphorus-containing_groups_(EC_2.7)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Kinases" title="Template:Kinases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Kinases" title="Template talk:Kinases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Kinases" title="Special:EditPage/Template:Kinases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_phosphorus-containing_groups_(EC_2.7)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a>-containing groups (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.7)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">2.7.1-2.7.4:<br /><a href="/wiki/Phosphotransferase" title="Phosphotransferase">phosphotransferase</a>/<a href="/wiki/Kinase" title="Kinase">kinase</a><br />(<a href="/wiki/Phosphate" title="Phosphate">PO<sub>4</sub></a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.1:_Phosphotransferases_with_an_Alcohol_Group_as_Acceptor" title="List of EC numbers (EC 2)">2.7.1</a>: <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">OH</a> acceptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexokinase" title="Hexokinase">Hexo-</a></li> <li><a href="/wiki/Glucokinase" title="Glucokinase">Gluco-</a></li> <li><a href="/wiki/Fructokinase" title="Fructokinase">Fructo-</a> <ul><li><a href="/wiki/Hepatic_fructokinase" title="Hepatic fructokinase">Hepatic</a></li></ul></li> <li><a href="/wiki/Galactokinase" title="Galactokinase">Galacto-</a></li> <li><a href="/wiki/Phosphofructokinase" title="Phosphofructokinase">Phosphofructo-</a> <ul><li><a href="/wiki/Phosphofructokinase_1" title="Phosphofructokinase 1">1</a></li> <li><a href="/wiki/PFKL" title="PFKL">Liver</a></li> <li><a href="/wiki/PFKM" title="PFKM">Muscle</a></li> <li><a href="/wiki/PFKP" title="PFKP">Platelet</a></li> <li><a href="/wiki/Phosphofructokinase_2" title="Phosphofructokinase 2">2</a></li></ul></li> <li><a href="/wiki/Riboflavin_kinase" title="Riboflavin kinase">Riboflavin</a></li> <li><a href="/wiki/Shikimate_kinase" title="Shikimate kinase">Shikimate</a></li> <li><a href="/wiki/Thymidine_kinase" title="Thymidine kinase">Thymidine</a> <ul><li><a href="/wiki/ADP%E2%80%94thymidine_kinase" title="ADP—thymidine kinase">ADP-thymidine</a></li></ul></li> <li><a href="/wiki/NAD%2B_kinase" title="NAD+ kinase">NAD<sup>+</sup></a></li> <li><a href="/wiki/Glycerol_kinase" title="Glycerol kinase">Glycerol</a></li> <li><a href="/wiki/Pantothenate_kinase" title="Pantothenate kinase">Pantothenate</a></li> <li><a href="/wiki/Mevalonate_kinase" title="Mevalonate kinase">Mevalonate</a></li> <li><a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">Pyruvate</a></li> <li><a href="/wiki/Deoxycytidine_kinase" title="Deoxycytidine kinase">Deoxycytidine</a></li> <li><a href="/wiki/PFP_(enzyme)" title="PFP (enzyme)">PFP</a></li> <li><a href="/wiki/Diacylglycerol_kinase" title="Diacylglycerol kinase">Diacylglycerol</a></li> <li><a href="/wiki/Phosphoinositide_3-kinase" title="Phosphoinositide 3-kinase">Phosphoinositide 3</a> <ul><li><a href="/wiki/Class_I_PI_3-kinases" title="Class I PI 3-kinases">Class I PI 3</a></li> <li><a href="/wiki/Class_II_PI_3-kinases" title="Class II PI 3-kinases">Class II PI 3</a></li></ul></li> <li><a href="/wiki/Sphingosine_kinase" title="Sphingosine kinase">Sphingosine</a></li> <li><a href="/wiki/Glucose-1,6-bisphosphate_synthase" title="Glucose-1,6-bisphosphate synthase">Glucose-1,6-bisphosphate synthase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.2:_Phosphotransferases_with_a_carboxy_group_as_acceptor" title="List of EC numbers (EC 2)">2.7.2</a>: <a href="/wiki/Carboxy" class="mw-redirect" title="Carboxy">COOH</a> acceptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphoglycerate_kinase" title="Phosphoglycerate kinase">Phosphoglycerate</a></li> <li><a href="/wiki/Aspartate_kinase" title="Aspartate kinase">Aspartate kinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.3:_Phosphotransferases_with_a_nitrogenous_group_as_acceptor" title="List of EC numbers (EC 2)">2.7.3</a>: <a href="/wiki/Nitrogen" title="Nitrogen">N</a> acceptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Creatine_kinase" title="Creatine kinase">Creatine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.4:_Phosphotransferases_with_a_phosphate_group_as_acceptor" title="List of EC numbers (EC 2)">2.7.4</a>: <a href="/wiki/Phosphate" title="Phosphate">PO<sub>4</sub></a> acceptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphomevalonate_kinase" title="Phosphomevalonate kinase">Phosphomevalonate</a></li> <li><a href="/wiki/Adenylate_kinase" title="Adenylate kinase">Adenylate</a></li> <li><a href="/wiki/Nucleoside-diphosphate_kinase" title="Nucleoside-diphosphate kinase">Nucleoside-diphosphate</a></li> <li><a href="/wiki/UMP_kinase" title="UMP kinase">Uridylate</a></li> <li><a href="/wiki/Guanylate_kinase" title="Guanylate kinase">Guanylate</a></li> <li><a href="/wiki/Thiamine-diphosphate_kinase" title="Thiamine-diphosphate kinase">Thiamine-diphosphate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.6:_Diphosphotransferases" title="List of EC numbers (EC 2)">2.7.6</a>: <a href="/wiki/Diphosphotransferase" title="Diphosphotransferase">diphosphotransferase</a><br />(<a href="/wiki/Diphosphate" class="mw-redirect" title="Diphosphate">P<sub>2</sub>O<sub>7</sub></a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ribose-phosphate_diphosphokinase" title="Ribose-phosphate diphosphokinase">Ribose-phosphate diphosphokinase</a></li> <li><a href="/wiki/Thiamine_diphosphokinase" title="Thiamine diphosphokinase">Thiamine diphosphokinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.7:_Nucleotidyltransferases" title="List of EC numbers (EC 2)">2.7.7</a>: <a href="/wiki/Nucleotidyltransferase" title="Nucleotidyltransferase">nucleotidyltransferase</a><br />(<a href="/wiki/Nucleoside_monophosphate" class="mw-redirect" title="Nucleoside monophosphate">PO<sub>4</sub>-nucleoside</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polymerase" title="Polymerase">Polymerase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DNA_polymerase" title="DNA polymerase">DNA polymerase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <dl><dt>DNA-directed DNA polymerase</dt> <dd><a href="/wiki/DNA_polymerase_I" title="DNA polymerase I">I</a>/A <dl><dd><a href="/wiki/POLG" title="POLG">γ</a></dd> <dd><a href="/wiki/POLQ" title="POLQ">θ</a></dd> <dd><a href="/wiki/DNA_polymerase_nu" title="DNA polymerase nu">ν</a></dd> <dd><a href="/wiki/T7_DNA_polymerase" title="T7 DNA polymerase">T7</a></dd> <dd><a href="/wiki/Taq_polymerase" title="Taq polymerase"><i>Taq</i></a></dd></dl></dd> <dd><a href="/wiki/DNA_polymerase_II" title="DNA polymerase II">II</a>/B <dl><dd><a href="/wiki/DNA_polymerase_alpha" title="DNA polymerase alpha">α</a></dd> <dd><a href="/wiki/DNA_polymerase_delta" title="DNA polymerase delta">δ</a></dd> <dd><a href="/wiki/DNA_polymerase_epsilon" title="DNA polymerase epsilon">ε</a></dd> <dd><a href="/wiki/REV3L" title="REV3L">ζ</a></dd> <dd><a href="/wiki/Pfu_DNA_polymerase" title="Pfu DNA polymerase"><i>Pfu</i></a></dd></dl></dd> <dd><a href="/wiki/DNA_polymerase_III_holoenzyme" title="DNA polymerase III holoenzyme">III</a>/C</dd> <dd><a href="/wiki/DNA_polymerase_IV" title="DNA polymerase IV">IV</a>/X <dl><dd><a href="/wiki/DNA_polymerase_beta" title="DNA polymerase beta">β</a></dd> <dd><a href="/wiki/DNA_polymerase_lambda" title="DNA polymerase lambda">λ</a></dd> <dd><a href="/wiki/DNA_polymerase_mu" title="DNA polymerase mu">μ</a></dd> <dd><a href="/wiki/Terminal_deoxynucleotidyl_transferase" title="Terminal deoxynucleotidyl transferase">TDT</a></dd></dl></dd> <dd><a href="/wiki/DNA_polymerase_V" title="DNA polymerase V">V</a>/Y <dl><dd><a href="/wiki/DNA_polymerase_eta" title="DNA polymerase eta">η</a></dd> <dd><a href="/wiki/POLI" title="POLI">ι</a></dd> <dd><a href="/wiki/POLK" title="POLK">κ</a></dd></dl></dd></dl> <dl><dt>RNA-directed DNA polymerase</dt> <dd><a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">Reverse transcriptase</a> <dl><dd><a href="/wiki/Telomerase" title="Telomerase">Telomerase</a></dd></dl></dd></dl> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <dl><dt><a href="/wiki/RNA_polymerase" title="RNA polymerase">Template-directed</a></dt> <dd><a href="/wiki/RNA_polymerase_I" title="RNA polymerase I">RNA polymerase I</a></dd> <dd><a href="/wiki/RNA_polymerase_II" title="RNA polymerase II">II</a></dd> <dd><a href="/wiki/RNA_polymerase_III" title="RNA polymerase III">III</a></dd> <dd><a href="/wiki/RNA_polymerase_IV" title="RNA polymerase IV">IV</a></dd> <dd><a href="/wiki/RNA_polymerase_V" title="RNA polymerase V">V</a></dd> <dd><a href="/wiki/T7_RNA_polymerase" title="T7 RNA polymerase">ssRNAP</a> <dl><dd><a href="/wiki/POLRMT" title="POLRMT">POLRMT</a></dd></dl></dd> <dd><a href="/wiki/Primase" title="Primase">Primase</a> <dl><dd><a href="/wiki/PRIM1" title="PRIM1">1</a></dd> <dd><a href="/wiki/PRIM2" title="PRIM2">2</a></dd> <dd><a href="/wiki/PrimPol" title="PrimPol">PrimPol</a></dd></dl></dd> <dd><a href="/wiki/RNA-dependent_RNA_polymerase" title="RNA-dependent RNA polymerase">RNA-dependent RNA polymerase</a></dd> <dt><a href="/wiki/Polyadenylation" title="Polyadenylation">Polyadenylation</a></dt> <dd><a href="/wiki/Polynucleotide_adenylyltransferase" title="Polynucleotide adenylyltransferase">PAP</a></dd> <dd><a href="/wiki/Polynucleotide_phosphorylase" title="Polynucleotide phosphorylase">PNPase</a></dd></dl> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorolysis" title="Phosphorolysis">Phosphorolytic</a><br />3' to 5' <a href="/wiki/Exoribonuclease" title="Exoribonuclease">exoribonuclease</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/RNase_PH" title="RNase PH">RNase PH</a></li> <li><a href="/wiki/Polynucleotide_phosphorylase" title="Polynucleotide phosphorylase">PNPase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleotidyltransferase" title="Nucleotidyltransferase">Nucleotidyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/UTP%E2%80%94glucose-1-phosphate_uridylyltransferase" title="UTP—glucose-1-phosphate uridylyltransferase">UTP—glucose-1-phosphate uridylyltransferase</a></li> <li><a href="/wiki/Galactose-1-phosphate_uridylyltransferase" title="Galactose-1-phosphate uridylyltransferase">Galactose-1-phosphate uridylyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Guanylyltransferase" title="Guanylyltransferase">Guanylyltransferase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/MRNA_capping_enzyme" class="mw-redirect" title="MRNA capping enzyme">mRNA capping enzyme</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Recombinase" title="Recombinase">Recombinase</a> (<a href="/wiki/Integrase" title="Integrase">Integrase</a>)</li> <li><a href="/wiki/Transposase" title="Transposase">Transposase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.8:_Transferases_for_other_substituted_phosphate_groups" title="List of EC numbers (EC 2)">2.7.8</a>: miscellaneous</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Phosphatidyltransferases</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CDP-diacylglycerol%E2%80%94glycerol-3-phosphate_3-phosphatidyltransferase" title="CDP-diacylglycerol—glycerol-3-phosphate 3-phosphatidyltransferase">CDP-diacylglycerol—glycerol-3-phosphate 3-phosphatidyltransferase</a></li> <li><a href="/wiki/CDP-diacylglycerol%E2%80%94serine_O-phosphatidyltransferase" title="CDP-diacylglycerol—serine O-phosphatidyltransferase">CDP-diacylglycerol—serine O-phosphatidyltransferase</a></li> <li><a href="/wiki/CDP-diacylglycerol%E2%80%94inositol_3-phosphatidyltransferase" title="CDP-diacylglycerol—inositol 3-phosphatidyltransferase">CDP-diacylglycerol—inositol 3-phosphatidyltransferase</a></li> <li><a href="/wiki/Phosphatidylcholine_synthase" title="Phosphatidylcholine synthase">CDP-diacylglycerol—choline O-phosphatidyltransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosyl-1-phosphotransferase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-acetylglucosamine-1-phosphate_transferase" title="N-acetylglucosamine-1-phosphate transferase">N-acetylglucosamine-1-phosphate transferase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">2.7.10-2.7.13: <a href="/wiki/Protein_kinase" title="Protein kinase">protein kinase</a><br />(<a href="/wiki/Phosphate" title="Phosphate">PO<sub>4</sub></a>; protein acceptor)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.10:_Protein-tyrosine_kinases" title="List of EC numbers (EC 2)">2.7.10</a>: <a href="/wiki/Tyrosine_kinase" title="Tyrosine kinase">protein-tyrosine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Tyrosine_kinase" title="Tyrosine kinase">tyrosine kinases</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.11:_Protein-serine/threonine_kinases" title="List of EC numbers (EC 2)">2.7.11</a>: <a href="/wiki/Serine/threonine-specific_protein_kinase" title="Serine/threonine-specific protein kinase">protein-serine/threonine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Template:Serine/threonine-specific_protein_kinases" title="Template:Serine/threonine-specific protein kinases">serine/threonine-specific protein kinases</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.12:_Dual-specificity_kinases_.28those_acting_on_Ser.2FThr_and_Tyr_residues.29" title="List of EC numbers (EC 2)">2.7.12</a>: protein-dual-specificity</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Template:Serine/threonine-specific_protein_kinases" title="Template:Serine/threonine-specific protein kinases">serine/threonine-specific protein kinases</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.7.13:_Protein-histidine_kinases" title="List of EC numbers (EC 2)">2.7.13</a>: protein-histidine</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein-histidine_pros-kinase" title="Protein-histidine pros-kinase">Protein-histidine pros-kinase</a></li> <li><a href="/wiki/Protein-histidine_tele-kinase" title="Protein-histidine tele-kinase">Protein-histidine tele-kinase</a></li> <li><a href="/wiki/Histidine_kinase" title="Histidine kinase">Histidine kinase</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_sulfur-containing_group_(EC_2.8)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Sulfur-containing_group_transferases" title="Template:Sulfur-containing group transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sulfur-containing_group_transferases" title="Template talk:Sulfur-containing group transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sulfur-containing_group_transferases" title="Special:EditPage/Template:Sulfur-containing group transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_sulfur-containing_group_(EC_2.8)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>-containing group (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.8)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.1:_Sulfurtransferases" title="List of EC numbers (EC 2)">2.8.1</a>: <a href="/wiki/Sulfurtransferase" title="Sulfurtransferase">Sulfurtransferases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiosulfate_sulfurtransferase" class="mw-redirect" title="Thiosulfate sulfurtransferase">Thiosulfate sulfurtransferase</a> <ul><li><a href="/wiki/Rhodanese" title="Rhodanese">Rhodanese</a></li></ul></li> <li><a href="/wiki/3-mercaptopyruvate_sulfurtransferase" title="3-mercaptopyruvate sulfurtransferase">3-mercaptopyruvate sulfurtransferase</a></li> <li><a href="/wiki/Thiosulfate%E2%80%94thiol_sulfurtransferase" title="Thiosulfate—thiol sulfurtransferase">thiosulfate—thiol sulfurtransferase</a></li> <li><a href="/wiki/TRNA_sulfurtransferase" title="TRNA sulfurtransferase">tRNA sulfurtransferase</a></li> <li><a href="/wiki/Thiosulfate%E2%80%94dithiol_sulfurtransferase" title="Thiosulfate—dithiol sulfurtransferase">thiosulfate—dithiol sulfurtransferase</a></li> <li><a href="/wiki/Biotin_synthase" title="Biotin synthase">biotin synthase</a></li> <li><a href="/wiki/Cysteine_desulfurase" title="Cysteine desulfurase">cysteine desulfurase</a></li> <li><a href="/wiki/Lipoyl_synthase" title="Lipoyl synthase">lipoyl synthase</a></li> <li><a href="/wiki/Molybdenum_cofactor_sulfurtransferase" title="Molybdenum cofactor sulfurtransferase">molybdenum cofactor sulfurtransferase</a></li> <li><a href="/wiki/Thiazole_synthase" title="Thiazole synthase">thiazole synthase</a></li> <li><a href="/wiki/Molybdopterin_synthase_sulfurtransferase" title="Molybdopterin synthase sulfurtransferase">molybdopterin synthase sulfurtransferase</a></li> <li><a href="/wiki/Molybdopterin_synthase" title="Molybdopterin synthase">molybdopterin synthase</a></li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">tRNA-uridine 2-sulfurtransferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">tRNA-5-taurinomethyluridine 2-sulfurtransferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">tRNA-5-methyluridine<sup>54</sup> 2-sulfurtransferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)"><small>L</small>-aspartate semialdehyde sulfurtransferase</a> (*)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.2:_Sulfotransferases" title="List of EC numbers (EC 2)">2.8.2</a>: <a href="/wiki/Sulfotransferase" title="Sulfotransferase">Sulfotransferases</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aryl_sulfotransferase" title="Aryl sulfotransferase">aryl sulfotransferase</a></li> <li><a href="/wiki/Amine_sulfotransferase" title="Amine sulfotransferase">amine sulfotransferase</a></li> <li><a href="/wiki/Estrone_sulfotransferase" title="Estrone sulfotransferase">estrone sulfotransferase</a></li> <li><a href="/wiki/Chondroitin_4-sulfotransferase" title="Chondroitin 4-sulfotransferase">chondroitin 4-sulfotransferase</a></li> <li><a href="/wiki/Choline_sulfotransferase" title="Choline sulfotransferase">choline sulfotransferase</a></li> <li><a href="/wiki/UDP-N-acetylgalactosamine-4-sulfate_sulfotransferase" title="UDP-N-acetylgalactosamine-4-sulfate sulfotransferase">UDP-N-acetylgalactosamine-4-sulfate sulfotransferase</a></li> <li><a href="/w/index.php?title=Heparan_sulfate-glucosamine_N-sulfotransferase&action=edit&redlink=1" class="new" title="Heparan sulfate-glucosamine N-sulfotransferase (page does not exist)">heparan sulfate-glucosamine N-sulfotransferase</a></li> <li><a href="/wiki/Tyrosine-ester_sulfotransferase" title="Tyrosine-ester sulfotransferase">tyrosine-ester sulfotransferase</a></li> <li><a href="/wiki/Renilla-luciferin_sulfotransferase" title="Renilla-luciferin sulfotransferase">Renilla-luciferin sulfotransferase</a></li> <li><a href="/wiki/Galactosylceramide_sulfotransferase" title="Galactosylceramide sulfotransferase">galactosylceramide sulfotransferase</a></li> <li><a href="/wiki/Psychosine_sulfotransferase" title="Psychosine sulfotransferase">psychosine sulfotransferase</a></li> <li><a href="/wiki/Bile_salt_sulfotransferase" title="Bile salt sulfotransferase">bile salt sulfotransferase</a></li> <li><a href="/wiki/Steroid_sulfotransferase" title="Steroid sulfotransferase">steroid sulfotransferase</a></li> <li><a href="/wiki/Thiol_sulfotransferase" title="Thiol sulfotransferase">thiol sulfotransferase</a></li> <li><a href="/wiki/Chondroitin_6-sulfotransferase" title="Chondroitin 6-sulfotransferase">chondroitin 6-sulfotransferase</a></li> <li><a href="/wiki/Cortisol_sulfotransferase" title="Cortisol sulfotransferase">cortisol sulfotransferase</a></li> <li><a href="/wiki/Triglucosylalkylacylglycerol_sulfotransferase" title="Triglucosylalkylacylglycerol sulfotransferase">triglucosylalkylacylglycerol sulfotransferase</a></li> <li><a href="/wiki/Protein-tyrosine_sulfotransferase" class="mw-redirect" title="Protein-tyrosine sulfotransferase">protein-tyrosine sulfotransferase</a></li> <li><a href="/wiki/Keratan_sulfotransferase" title="Keratan sulfotransferase">keratan sulfotransferase</a></li> <li><a href="/wiki/Aryl-sulfate_sulfotransferase" title="Aryl-sulfate sulfotransferase">aryl-sulfate sulfotransferase</a></li> <li><a href="/wiki/(heparan_sulfate)-glucosamine_3-sulfotransferase_1" title="(heparan sulfate)-glucosamine 3-sulfotransferase 1">(heparan sulfate)-glucosamine 3-sulfotransferase 1</a></li> <li><a href="/wiki/Desulfoglucosinolate_sulfotransferase" title="Desulfoglucosinolate sulfotransferase">desulfoglucosinolate sulfotransferase</a></li> <li><a href="/wiki/Flavonol_3-sulfotransferase" title="Flavonol 3-sulfotransferase">flavonol 3-sulfotransferase</a></li> <li><a href="/wiki/Quercetin-3-sulfate_3%27-sulfotransferase" title="Quercetin-3-sulfate 3'-sulfotransferase">quercetin-3-sulfate 3′-sulfotransferase</a></li> <li><a href="/wiki/Quercetin-3-sulfate_4%27-sulfotransferase" title="Quercetin-3-sulfate 4'-sulfotransferase">quercetin-3-sulfate 4′-sulfotransferase</a></li> <li><a href="/w/index.php?title=Quercetin-3,3%E2%80%B2-bissulfate_7-sulfotransferase&action=edit&redlink=1" class="new" title="Quercetin-3,3′-bissulfate 7-sulfotransferase (page does not exist)">quercetin-3,3′-bissulfate 7-sulfotransferase</a></li> <li><a href="/wiki/(heparan_sulfate)-glucosamine_3-sulfotransferase_2" title="(heparan sulfate)-glucosamine 3-sulfotransferase 2">(heparan sulfate)-glucosamine 3-sulfotransferase 2</a></li> <li><a href="/wiki/(heparan_sulfate)-glucosamine_3-sulfotransferase_3" title="(heparan sulfate)-glucosamine 3-sulfotransferase 3">(heparan sulfate)-glucosamine 3-sulfotransferase 3</a></li> <li><a href="/wiki/Petromyzonol_sulfotransferase" title="Petromyzonol sulfotransferase">petromyzonol sulfotransferase</a></li> <li><a href="/wiki/Scymnol_sulfotransferase" title="Scymnol sulfotransferase">scymnol sulfotransferase</a></li> <li><a href="/wiki/N-acetylgalactosamine_4-sulfate_6-O-sulfotransferase" title="N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase">N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase</a></li> <li><a href="/wiki/Glycochenodeoxycholate_sulfotransferase" title="Glycochenodeoxycholate sulfotransferase">glycochenodeoxycholate sulfotransferase</a></li> <li><a href="/wiki/Dermatan_4-sulfotransferase" title="Dermatan 4-sulfotransferase">dermatan 4-sulfotransferase</a></li> <li><a href="/w/index.php?title=Desulfo-A47934_sulfotransferase_(*)&action=edit&redlink=1" class="new" title="Desulfo-A47934 sulfotransferase (*) (page does not exist)">desulfo-A47934 sulfotransferase (*)</a></li> <li><a href="/w/index.php?title=Trehalose_2-sulfotransferase_(*)&action=edit&redlink=1" class="new" title="Trehalose 2-sulfotransferase (*) (page does not exist)">trehalose 2-sulfotransferase (*)</a></li> <li><a href="/w/index.php?title=Aliphatic_desulfoglucosinolate_sulfotransferase_(*)&action=edit&redlink=1" class="new" title="Aliphatic desulfoglucosinolate sulfotransferase (*) (page does not exist)">aliphatic desulfoglucosinolate sulfotransferase (*)</a></li> <li><a href="/w/index.php?title=Hydroxyjasmonate_sulfotransferase_(*)&action=edit&redlink=1" class="new" title="Hydroxyjasmonate sulfotransferase (*) (page does not exist)">hydroxyjasmonate sulfotransferase (*)</a></li> <li><a href="/w/index.php?title=%CE%A9-hydroxy-%CE%B2-dihydromenaquinone-9_sulfotransferase_(*)&action=edit&redlink=1" class="new" title="Ω-hydroxy-β-dihydromenaquinone-9 sulfotransferase (*) (page does not exist)">ω-hydroxy-β-dihydromenaquinone-9 sulfotransferase (*)</a></li> <li><a href="/wiki/Alcohol_sulfotransferase" title="Alcohol sulfotransferase">Alcohol sulfotransferase</a></li> <li><a href="/wiki/Tyrosylprotein_sulfotransferase" title="Tyrosylprotein sulfotransferase">Tyrosylprotein sulfotransferase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.3:_CoA-transferases" title="List of EC numbers (EC 2)">2.8.3</a>: <a href="/wiki/Coenzyme_A" title="Coenzyme A">CoA-transferases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propionate_CoA-transferase" title="Propionate CoA-transferase">Propionate CoA-transferase</a></li> <li><a href="/wiki/Oxalate_CoA-transferase" title="Oxalate CoA-transferase">oxalate CoA-transferase</a></li> <li><a href="/wiki/Malonate_CoA-transferase" title="Malonate CoA-transferase">malonate CoA-transferase</a></li> <li><a href="/wiki/3-oxoacid_CoA-transferase" title="3-oxoacid CoA-transferase">3-oxoacid CoA-transferase</a></li> <li><a href="/wiki/3-oxoadipate_CoA-transferase" title="3-oxoadipate CoA-transferase">3-oxoadipate CoA-transferase</a></li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">succinyl-CoA—<small>D</small>citramalate CoA-transferase</a></li> <li><a href="/wiki/Acetate_CoA-transferase" title="Acetate CoA-transferase">acetate CoA-transferase</a></li> <li><a href="/wiki/Butyrate%E2%80%94acetoacetate_CoA-transferase" title="Butyrate—acetoacetate CoA-transferase">butyrate—acetoacetate CoA-transferase</a></li> <li><a href="/wiki/Citrate_CoA-transferase" title="Citrate CoA-transferase">citrate CoA-transferase</a></li> <li><a href="/wiki/Citramalate_CoA-transferase" title="Citramalate CoA-transferase">citramalate CoA-transferase</a></li> <li><a href="/wiki/Glutaconate_CoA-transferase" title="Glutaconate CoA-transferase">glutaconate CoA-transferase</a></li> <li><a href="/wiki/Succinate%E2%80%94hydroxymethylglutarate_CoA-transferase" title="Succinate—hydroxymethylglutarate CoA-transferase">succinate—hydroxymethylglutarate CoA-transferase</a></li> <li><a href="/wiki/5-hydroxypentanoate_CoA-transferase" title="5-hydroxypentanoate CoA-transferase">5-hydroxypentanoate CoA-transferase</a></li> <li><a href="/wiki/Succinyl-CoA:(R)-benzylsuccinate_CoA-transferase" title="Succinyl-CoA:(R)-benzylsuccinate CoA-transferase">succinyl-CoA:(<i>R</i>)-benzylsuccinate CoA-transferase</a></li> <li><a href="/wiki/Formyl-CoA_transferase" title="Formyl-CoA transferase">formyl-CoA transferase</a></li> <li><a href="/wiki/Cinnamoyl-CoA:phenyllactate_CoA-transferase" title="Cinnamoyl-CoA:phenyllactate CoA-transferase">cinnamoyl-CoA:phenyllactate CoA-transferase</a></li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">succinyl-CoA:acetate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">CoA:oxalate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">succinyl-CoA—<small>D</small>-citramalate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)"><small>L</small>-carnitine CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">succinyl-CoA—<small>L</small>-malate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">caffeate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">(<i>R</i>)-2-hydroxy-4-methylpentanoate CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">bile acid CoA-transferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">succinyl-CoA:mesaconate CoA transferase</a> (*)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.4:_Transferring_alkylthio_groups" title="List of EC numbers (EC 2)">2.8.4</a>: Alkylthio</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.5:_Transferring_alkylthio_groups" title="List of EC numbers (EC 2)">2.8.4</a>: <ul><li><a href="/wiki/Coenzyme-B_sulfoethylthiotransferase" title="Coenzyme-B sulfoethylthiotransferase">Coenzyme-B sulfoethylthiotransferase</a></li> <li><a href="/wiki/Arsenate-mycothiol_transferase" title="Arsenate-mycothiol transferase">arsenate-mycothiol transferase</a></li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">tRNA-2-methylthio-<i>N</i><sup>6</sup>-dimethylallyladenosine synthase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">[ribosomal protein S12] (aspartate<sup>89</sup>-<i>C</i><sup>3</sup>)-methylthiotransferase</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)">tRNA (<i>N</i><sup>6</sup>-<small>L</small>-threonylcarbamoyladenosine<sup>37</sup>-<i>C</i><sup>2</sup>)-methylthiotransferase</a> (*)</li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.5:_Transferring_Thiosulfo_groups" title="List of EC numbers (EC 2)">2.8.5</a>:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.8.5:_Transferring_Thiosulfo_groups" title="List of EC numbers (EC 2)">2.8.5</a>: <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)"><i>S</i>-sulfo-<small>L</small>-cysteine synthase (3-phospho-<small>L</small>-serine-dependent)</a> (*)</li> <li><a href="/w/index.php?title=NoWikiArt&action=edit&redlink=1" class="new" title="NoWikiArt (page does not exist)"><small>L</small>-cysteine <i>S</i>-thiosulfotransferase</a> (*)</li></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Transferases:_selenium-containing_group_(EC_2.9)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Selenium-containing_group_transferases" title="Template:Selenium-containing group transferases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Selenium-containing_group_transferases" title="Template talk:Selenium-containing group transferases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Selenium-containing_group_transferases" title="Special:EditPage/Template:Selenium-containing group transferases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transferases:_selenium-containing_group_(EC_2.9)" style="font-size:114%;margin:0 4em"><a href="/wiki/Transferase" title="Transferase">Transferases</a>: <a href="/wiki/Selenium" title="Selenium">selenium</a>-containing group (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 2.9)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_2)#EC_2.9:_Transferring_Selenium-Containing_Groups" title="List of EC numbers (EC 2)">2.9.1</a>: <a href="/wiki/Selenotransferase" title="Selenotransferase">Selenotransferases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/L-seryl-tRNASec_selenium_transferase" title="L-seryl-tRNASec selenium transferase">L-seryl-tRNASec selenium transferase</a></li> <li><a href="/wiki/O-phospho-L-seryl-tRNASec:L-selenocysteinyl-tRNA_synthase" title="O-phospho-L-seryl-tRNASec:L-selenocysteinyl-tRNA synthase">O-phospho-L-seryl-tRNASec:L-selenocysteinyl-tRNA synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerases:_Epimerase_and_racemases_(EC_5.1)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Racemases_and_epimerases" title="Template:Racemases and epimerases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Racemases_and_epimerases" title="Template talk:Racemases and epimerases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Racemases_and_epimerases" title="Special:EditPage/Template:Racemases and epimerases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerases:_Epimerase_and_racemases_(EC_5.1)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerases</a>: <a href="/wiki/Epimerase_and_racemase" title="Epimerase and racemase">Epimerase and racemases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.1)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.1.1:_Acting_on_Amino_acids_and_Derivatives" title="List of EC numbers (EC 5)">5.1.1</a>: <a href="/wiki/Amino_acid" title="Amino acid">Amino acids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amino-acid_racemase" title="Amino-acid racemase">Amino-acid racemase</a>: <a href="/wiki/Phenylalanine_racemase_(ATP-hydrolysing)" title="Phenylalanine racemase (ATP-hydrolysing)">Phenylalanine racemase (ATP-hydrolysing)</a></li> <li><a href="/wiki/Serine_racemase" title="Serine racemase">Serine racemase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.1.2:_Acting_on_Hydroxy_acids_and_Derivatives" title="List of EC numbers (EC 5)">5.1.2</a>: <a href="/wiki/Alpha_hydroxy_acid" class="mw-redirect" title="Alpha hydroxy acid">Hydroxy acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mandelate_racemase" title="Mandelate racemase">Mandelate racemase</a></li> <li><a href="/wiki/Isocitrate_epimerase" title="Isocitrate epimerase">Isocitrate epimerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.1.3:_Acting_on_Carbohydrates_and_Derivatives" title="List of EC numbers (EC 5)">5.1.3</a>: <a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/UDP-glucose_4-epimerase" title="UDP-glucose 4-epimerase">UDP-glucose 4-epimerase</a></li> <li><a href="/wiki/N-acetylneuraminate_epimerase" title="N-acetylneuraminate epimerase">N-acetylneuraminate epimerase</a></li> <li><a href="/wiki/Phosphopentose_epimerase" title="Phosphopentose epimerase">Phosphopentose epimerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.1.99:_Acting_on_Other_Compounds" title="List of EC numbers (EC 5)">5.1.99</a>: Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl_CoA_epimerase" title="Methylmalonyl CoA epimerase">Methylmalonyl CoA epimerase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerases:_geometric_(EC_5.2)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Geometric_isomerases" title="Template:Geometric isomerases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Geometric_isomerases" title="Template talk:Geometric isomerases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Geometric_isomerases" title="Special:EditPage/Template:Geometric isomerases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerases:_geometric_(EC_5.2)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerases</a>: <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">geometric</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.2)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.2:_cis-trans-Isomerases" title="List of EC numbers (EC 5)">5.2.1</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/FKBP" title="FKBP">FKBP</a>: <a href="/wiki/FKBP1A" title="FKBP1A">FKBP1A</a></li> <li><a href="/wiki/FKBP1B" title="FKBP1B">FKBP1B</a></li> <li><a href="/wiki/FKBP2" title="FKBP2">FKBP2</a></li> <li><a href="/wiki/FKBP3" title="FKBP3">FKBP3</a></li> <li><a href="/wiki/FKBP4" title="FKBP4">FKBP4</a></li> <li><a href="/wiki/FKBP5" title="FKBP5">FKBP5</a></li> <li><a href="/wiki/FKBP6" title="FKBP6">FKBP6</a></li> <li><a href="/wiki/FKBP8" title="FKBP8">FKBP8</a></li> <li><a href="/wiki/FKBP9" title="FKBP9">FKBP9</a></li> <li><a href="/wiki/FKBP10" title="FKBP10">FKBP10</a></li> <li><a href="/wiki/FKBPL" title="FKBPL">FKBPL</a></li></ul> <ul><li>other: <a href="/wiki/Cyclophilin" title="Cyclophilin">Cyclophilin</a></li> <li><a href="/wiki/Parvulin" title="Parvulin">Parvulin</a></li> <li><a href="/wiki/Prolyl_isomerase" title="Prolyl isomerase">Prolyl isomerase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerases:_intramolecular_oxidoreductases_(EC_5.3)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Intramolecular_oxidoreductases" title="Template:Intramolecular oxidoreductases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Intramolecular_oxidoreductases" title="Template talk:Intramolecular oxidoreductases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Intramolecular_oxidoreductases" title="Special:EditPage/Template:Intramolecular oxidoreductases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerases:_intramolecular_oxidoreductases_(EC_5.3)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerases</a>: intramolecular <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.3)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.1:_Interconverting_Aldoses_and_Ketoses" title="List of EC numbers (EC 5)">5.3.1</a>: <a href="/wiki/Aldose" title="Aldose">Aldoses</a>/<a href="/wiki/Ketose" title="Ketose">Ketoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Triosephosphate_isomerase" title="Triosephosphate isomerase">Triosephosphate isomerase</a></li> <li><a href="/wiki/Ribose-5-phosphate_isomerase" title="Ribose-5-phosphate isomerase">Ribose-5-phosphate isomerase</a></li> <li><a href="/wiki/Mannose_phosphate_isomerase" title="Mannose phosphate isomerase">Mannose phosphate isomerase</a></li> <li><a href="/wiki/Xylose_isomerase" title="Xylose isomerase">Glucose isomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.2:_Interconverting_Keto-_and_Enol-Groups" title="List of EC numbers (EC 5)">5.3.2</a>: <a class="mw-selflink selflink">Keto</a>/<a href="/wiki/Enol" title="Enol">Enol</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phenylpyruvate_tautomerase" title="Phenylpyruvate tautomerase">Phenylpyruvate tautomerase</a></li> <li><a href="/wiki/Oxaloacetate_tautomerase" title="Oxaloacetate tautomerase">Oxaloacetate tautomerase</a></li> <li><a href="/wiki/4-Oxalocrotonate_tautomerase" title="4-Oxalocrotonate tautomerase">4-Oxalocrotonate tautomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.3:_Transposing_C.3DC_Bonds" title="List of EC numbers (EC 5)">5.3.3</a>: C = C</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Steroid_Delta-isomerase" title="Steroid Delta-isomerase">Steroid D-isomerase</a></li> <li><a href="/wiki/Isopentenyl-diphosphate_delta_isomerase" title="Isopentenyl-diphosphate delta isomerase">Isopentenyl-diphosphate delta isomerase</a></li> <li><a href="/wiki/Vinylacetyl-CoA_Delta-isomerase" title="Vinylacetyl-CoA Delta-isomerase">Vinylacetyl-CoA D-isomerase</a></li> <li><a href="/wiki/Muconolactone_Delta-isomerase" class="mw-redirect" title="Muconolactone Delta-isomerase">Muconolactone D-isomerase</a></li> <li><a href="/wiki/Cholestenol_Delta-isomerase" title="Cholestenol Delta-isomerase">Cholestenol Delta-isomerase</a> (<a href="/wiki/Emopamil_binding_protein" title="Emopamil binding protein">EBP</a>)</li> <li><a href="/wiki/Methylitaconate_Delta-isomerase" title="Methylitaconate Delta-isomerase">Methylitaconate D-isomerase</a></li> <li><a href="/wiki/Aconitate_Delta-isomerase" title="Aconitate Delta-isomerase">Aconitate Delta-isomerase</a></li> <li><a href="/wiki/Enoyl_CoA_isomerase" title="Enoyl CoA isomerase">Enoyl CoA isomerase</a></li> <li><a href="/wiki/Prostaglandin-A1_Delta-isomerase" title="Prostaglandin-A1 Delta-isomerase">Prostaglandin-A1 Delta-isomerase</a></li> <li><a href="/wiki/5-carboxymethyl-2-hydroxymuconate_Delta-isomerase" title="5-carboxymethyl-2-hydroxymuconate Delta-isomerase">5-carboxymethyl-2-hydroxymuconate D-isomerase</a></li> <li><a href="/wiki/Isopiperitenone_Delta-isomerase" title="Isopiperitenone Delta-isomerase">Isopiperitenone D-isomerase</a></li> <li><a href="/wiki/L-dopachrome_isomerase" title="L-dopachrome isomerase">L-dopachrome isomerase</a></li> <li><a href="/wiki/Polyenoic_fatty_acid_isomerase" title="Polyenoic fatty acid isomerase">Polyenoic fatty acid isomerase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.4:_Transposing_S-S_Bonds" title="List of EC numbers (EC 5)">5.3.4</a>: S-S</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein_disulfide-isomerase" title="Protein disulfide-isomerase">Protein disulfide-isomerase</a> (<a href="/wiki/PDIA3" title="PDIA3">PDIA3</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.3.99:_Other_Intramolecular_Oxidoreductases" title="List of EC numbers (EC 5)">5.3.99</a>: other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostaglandin_D2_synthase" title="Prostaglandin D2 synthase">Prostaglandin D2 synthase</a>/<a href="/wiki/Prostaglandin-D_synthase" title="Prostaglandin-D synthase">Prostaglandin-D synthase</a></li> <li><a href="/wiki/Prostaglandin_E_synthase" title="Prostaglandin E synthase">Prostaglandin E synthase</a></li> <li><a href="/wiki/Prostacyclin_synthase" title="Prostacyclin synthase">Prostacyclin synthase</a></li> <li><a href="/wiki/Thromboxane-A_synthase" title="Thromboxane-A synthase">Thromboxane-A synthase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerase:_mutases_(EC_5.4)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mutases" title="Template:Mutases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mutases" title="Template talk:Mutases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mutases" title="Special:EditPage/Template:Mutases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerase:_mutases_(EC_5.4)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerase</a>: <a href="/wiki/Mutase" title="Mutase">mutases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.4)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.4.1:_Transferring_Acyl_Groups" title="List of EC numbers (EC 5)">5.4.1</a> Acyl Groups</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysolecithin_acylmutase" title="Lysolecithin acylmutase">Lysolecithin acylmutase</a></li> <li><a href="/wiki/Precorrin-8X_methylmutase" title="Precorrin-8X methylmutase">Precorrin-8X methylmutase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.4.2:_Phosphotransferases_.28Phosphomutases.29" title="List of EC numbers (EC 5)">5.4.2</a> Phosphomutases</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphoglycerate_mutase" title="Phosphoglycerate mutase">Phosphoglycerate mutase</a></li> <li><a href="/wiki/Bisphosphoglycerate_mutase" title="Bisphosphoglycerate mutase">Bisphosphoglycerate mutase</a></li> <li><a href="/wiki/Phosphoglucomutase" title="Phosphoglucomutase">Phosphoglucomutase</a></li> <li><a href="/wiki/Phosphomannomutase" title="Phosphomannomutase">Phosphomannomutase</a> <ul><li><a href="/wiki/PMM1" title="PMM1">PMM1</a></li> <li><a href="/wiki/PMM2" title="PMM2">PMM2</a></li></ul></li> <li><a href="/wiki/Phosphoenolpyruvate_mutase" title="Phosphoenolpyruvate mutase">Phosphoenolpyruvate mutase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.4.99:_Transferring_Other_Groups" title="List of EC numbers (EC 5)">5.4.99</a> Other groups</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cycloartenol_synthase" title="Cycloartenol synthase">Cycloartenol synthase</a></li> <li><a href="/wiki/Lanosterol_synthase" title="Lanosterol synthase">Lanosterol synthase</a></li> <li><a href="/wiki/Lupeol_synthase" title="Lupeol synthase">Lupeol synthase</a></li> <li><a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">Methylmalonyl-CoA mutase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerase:_Intramolecular_Lyases_(EC_5.5)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Intramolecular_Lyases" title="Template:Intramolecular Lyases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Intramolecular_Lyases" title="Template talk:Intramolecular Lyases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Intramolecular_Lyases" title="Special:EditPage/Template:Intramolecular Lyases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerase:_Intramolecular_Lyases_(EC_5.5)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerase</a>: <a href="/wiki/Isomerase" title="Isomerase">Intramolecular Lyases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.5)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.5:_Intramolecular_Lyases" title="List of EC numbers (EC 5)">5.5.1</a> Intramolecular Lyases</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Muconate_cycloisomerase" class="mw-redirect" title="Muconate cycloisomerase">muconate cycloisomerase</a></li> <li><a href="/wiki/3-carboxy-cis,cis-muconate_cycloisomerase" title="3-carboxy-cis,cis-muconate cycloisomerase">3-carboxy-cis,cis-muconate cycloisomerase</a></li> <li><a href="/wiki/Tetrahydroxypteridine_cycloisomerase" title="Tetrahydroxypteridine cycloisomerase">tetrahydroxypteridine cycloisomerase</a></li> <li><a href="/wiki/Inositol-3-phosphate_synthase" title="Inositol-3-phosphate synthase">inositol-3-phosphate synthase</a></li> <li><a href="/wiki/Carboxy-cis,cis-muconate_cyclase" title="Carboxy-cis,cis-muconate cyclase">carboxy-cis,cis-muconate cyclase</a></li> <li><a href="/wiki/Chalcone_isomerase" title="Chalcone isomerase">chalcone isomerase</a></li> <li><a href="/wiki/Chloromuconate_cycloisomerase" title="Chloromuconate cycloisomerase">chloromuconate cycloisomerase</a></li> <li><a href="/wiki/Bornyl_diphosphate_synthase" title="Bornyl diphosphate synthase">bornyl diphosphate synthase</a></li> <li><a href="/wiki/Cycloeucalenol_cycloisomerase" title="Cycloeucalenol cycloisomerase">cycloeucalenol cycloisomerase</a></li> <li><a href="/wiki/A-pinene-oxide_decyclase" class="mw-redirect" title="A-pinene-oxide decyclase">a-pinene-oxide decyclase</a></li> <li><a href="/wiki/Dichloromuconate_cycloisomerase" title="Dichloromuconate cycloisomerase">dichloromuconate cycloisomerase</a></li> <li><a href="/wiki/Copalyl_diphosphate_synthase" title="Copalyl diphosphate synthase">copalyl diphosphate synthase</a></li> <li><a href="/wiki/Ent-copalyl_diphosphate_synthase" class="mw-redirect" title="Ent-copalyl diphosphate synthase">ent-copalyl diphosphate synthase</a></li> <li><a href="/wiki/Syn-copalyl-diphosphate_synthase" title="Syn-copalyl-diphosphate synthase">syn-copalyl-diphosphate synthase</a></li> <li><a href="/wiki/Terpentedienyl-diphosphate_synthase" title="Terpentedienyl-diphosphate synthase">terpentedienyl-diphosphate synthase</a></li> <li><a href="/wiki/Halimadienyl-diphosphate_synthase" title="Halimadienyl-diphosphate synthase">halimadienyl-diphosphate synthase</a></li> <li><a href="/wiki/(S)-beta-macrocarpene_synthase" title="(S)-beta-macrocarpene synthase">(S)-beta-macrocarpene synthase</a></li> <li><a href="/wiki/Lycopene_epsilon-cyclase" title="Lycopene epsilon-cyclase">lycopene epsilon-cyclase</a></li> <li><a href="/wiki/Lycopene_beta-cyclase" title="Lycopene beta-cyclase">lycopene beta-cyclase</a></li> <li><a href="/wiki/Prosolanapyrone-III_cycloisomerase" title="Prosolanapyrone-III cycloisomerase">prosolanapyrone-III cycloisomerase</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Isomerase:_topoisomerases_(EC_5.6)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Topoisomerases" title="Template:Topoisomerases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Topoisomerases" title="Template talk:Topoisomerases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Topoisomerases" title="Special:EditPage/Template:Topoisomerases"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Isomerase:_topoisomerases_(EC_5.6)" style="font-size:114%;margin:0 4em"><a href="/wiki/Isomerase" title="Isomerase">Isomerase</a>: <a href="/wiki/Topoisomerase" title="Topoisomerase">topoisomerases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 5.6)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_EC_numbers_(EC_5)#EC_5.6.2:_Enzymes_altering_nucleic_acid_conformation" title="List of EC numbers (EC 5)">5.6.2</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Type_I_topoisomerase" title="Type I topoisomerase">Type I topoisomerase</a></li> <li><a href="/wiki/Type_II_topoisomerase" title="Type II topoisomerase">Type II topoisomerase</a> <ul><li><a href="/wiki/DNA_gyrase" title="DNA gyrase">gyrase</a></li> <li><a href="/wiki/Topoisomerase_IV" title="Topoisomerase IV">topoisomerase IV</a></li></ul></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div 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