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class="vector-toc-numb">2</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Classification</span> </div> </a> <button aria-controls="toc-Classification-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 Classification subsection</span> </button> <ul id="toc-Classification-sublist" class="vector-toc-list"> <li id="toc-Racemases,_epimerases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Racemases,_epimerases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Racemases, epimerases</span> </div> </a> <ul id="toc-Racemases,_epimerases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cis-trans_isomerases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cis-trans_isomerases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cis-trans isomerases</span> </div> </a> <ul id="toc-Cis-trans_isomerases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_oxidoreductases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_oxidoreductases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Intramolecular oxidoreductases</span> </div> </a> <ul id="toc-Intramolecular_oxidoreductases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_transferases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_transferases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Intramolecular transferases</span> </div> </a> <ul id="toc-Intramolecular_transferases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_lyases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_lyases"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Intramolecular lyases</span> </div> </a> <ul id="toc-Intramolecular_lyases-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Mechanisms_of_isomerases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanisms_of_isomerases"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Mechanisms of isomerases</span> </div> </a> <button aria-controls="toc-Mechanisms_of_isomerases-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 Mechanisms of isomerases subsection</span> </button> <ul id="toc-Mechanisms_of_isomerases-sublist" class="vector-toc-list"> <li id="toc-Ring_expansion_and_contraction_via_tautomers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ring_expansion_and_contraction_via_tautomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Ring expansion and contraction via tautomers</span> </div> </a> <ul id="toc-Ring_expansion_and_contraction_via_tautomers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epimerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epimerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Epimerization</span> </div> </a> <ul id="toc-Epimerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_transfer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_transfer"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Intramolecular transfer</span> </div> </a> <ul id="toc-Intramolecular_transfer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramolecular_oxidoreduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramolecular_oxidoreduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Intramolecular oxidoreduction</span> </div> </a> <ul id="toc-Intramolecular_oxidoreduction-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-The_role_of_isomerase_in_human_disease" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#The_role_of_isomerase_in_human_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>The role of isomerase in human disease</span> </div> </a> <button aria-controls="toc-The_role_of_isomerase_in_human_disease-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 The role of isomerase in human disease subsection</span> </button> <ul id="toc-The_role_of_isomerase_in_human_disease-sublist" class="vector-toc-list"> <li id="toc-Phosphohexose_isomerase_deficiency" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphohexose_isomerase_deficiency"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Phosphohexose isomerase deficiency</span> </div> </a> <ul id="toc-Phosphohexose_isomerase_deficiency-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Triosephosphate_isomerase_deficiency" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Triosephosphate_isomerase_deficiency"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Triosephosphate isomerase deficiency</span> </div> </a> <ul id="toc-Triosephosphate_isomerase_deficiency-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Industrial_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Industrial applications</span> </div> </a> <ul id="toc-Industrial_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Membrane-associated_isomerases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Membrane-associated_isomerases"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Membrane-associated isomerases</span> </div> </a> <ul id="toc-Membrane-associated_isomerases-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">8</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">9</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 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Available in 34 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-34" 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">34 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%B2%D9%88%D9%85%D9%8A%D8%B1%D8%A7%D8%B2" title="إيزوميراز – Arabic" lang="ar" hreflang="ar" data-title="إيزوميراز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%86%D0%B7%D0%B0%D0%BC%D0%B5%D1%80%D0%B0%D0%B7%D1%8B" title="Ізамеразы – Belarusian" lang="be" hreflang="be" data-title="Ізамеразы" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%98%D0%B7%D0%BE%D0%BC%D0%B5%D1%80%D0%B0%D0%B7%D0%B0" title="Изомераза – Bulgarian" lang="bg" hreflang="bg" data-title="Изомераза" 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/Izomeraza" title="Izomeraza – Bosnian" lang="bs" hreflang="bs" data-title="Izomeraza" 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/Isomerasa" title="Isomerasa – Catalan" lang="ca" hreflang="ca" data-title="Isomerasa" 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/Izomer%C3%A1za" title="Izomeráza – Czech" lang="cs" hreflang="cs" data-title="Izomeráza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Isomerase" title="Isomerase – Danish" lang="da" hreflang="da" data-title="Isomerase" 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/Isomerasen" title="Isomerasen – German" lang="de" hreflang="de" data-title="Isomerasen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Isomerasa" title="Isomerasa – Spanish" lang="es" hreflang="es" data-title="Isomerasa" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B2%D9%88%D9%85%D8%B1%D8%A7%D8%B2" title="ایزومراز – Persian" lang="fa" hreflang="fa" data-title="ایزومراز" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Isom%C3%A9rase" title="Isomérase – French" lang="fr" hreflang="fr" data-title="Isomérase" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Isomerase" title="Isomerase – Galician" lang="gl" hreflang="gl" data-title="Isomerase" 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%9D%B4%EC%84%B1%EC%A7%88%ED%99%94_%ED%9A%A8%EC%86%8C" title="이성질화 효소 – Korean" lang="ko" hreflang="ko" data-title="이성질화 효소" 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%BB%D5%A6%D5%B8%D5%B4%D5%A5%D6%80%D5%A1%D5%A6%D5%B6%D5%A5%D6%80" title="Իզոմերազներ – Armenian" lang="hy" hreflang="hy" data-title="Իզոմերազներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Isomerasi" title="Isomerasi – Italian" lang="it" hreflang="it" data-title="Isomerasi" 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%90%D7%99%D7%96%D7%95%D7%9E%D7%A8%D7%90%D7%96" title="איזומראז – Hebrew" lang="he" hreflang="he" data-title="איזומראז" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%90%E0%B2%B8%E0%B3%8A%E0%B2%AE%E0%B2%B0%E0%B3%87%E0%B2%B8%E0%B3%81%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಐಸೊಮರೇಸುಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಐಸೊಮರೇಸುಗಳು" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Izomeraz%C4%97" title="Izomerazė – Lithuanian" lang="lt" hreflang="lt" data-title="Izomerazė" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Isomerase" title="Isomerase – Malay" lang="ms" hreflang="ms" data-title="Isomerase" 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/Isomerase" title="Isomerase – Dutch" lang="nl" hreflang="nl" data-title="Isomerase" 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/%E7%95%B0%E6%80%A7%E5%8C%96%E9%85%B5%E7%B4%A0" title="異性化酵素 – Japanese" lang="ja" hreflang="ja" data-title="異性化酵素" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Isomerase" title="Isomerase – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Isomerase" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Izomerazy" title="Izomerazy – Polish" lang="pl" hreflang="pl" data-title="Izomerazy" 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/Isomerase" title="Isomerase – Portuguese" lang="pt" hreflang="pt" data-title="Isomerase" 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/Izomeraz%C4%83" title="Izomerază – Romanian" lang="ro" hreflang="ro" data-title="Izomerază" 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%98%D0%B7%D0%BE%D0%BC%D0%B5%D1%80%D0%B0%D0%B7%D1%8B" title="Изомеразы – Russian" lang="ru" hreflang="ru" data-title="Изомеразы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Izomer%C3%A1za" title="Izomeráza – Slovak" lang="sk" hreflang="sk" data-title="Izomeráza" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Izomeraza" title="Izomeraza – Serbian" lang="sr" hreflang="sr" data-title="Izomeraza" 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/Izomeraza" title="Izomeraza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Izomeraza" 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/Isomeraasit" title="Isomeraasit – Finnish" lang="fi" hreflang="fi" data-title="Isomeraasit" 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/Isomeras" title="Isomeras – Swedish" lang="sv" hreflang="sv" data-title="Isomeras" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C4%B0zomeraz" title="İzomeraz – Turkish" lang="tr" hreflang="tr" data-title="İzomeraz" 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%86%D0%B7%D0%BE%D0%BC%D0%B5%D1%80%D0%B0%D0%B7%D0%B8" title="Ізомерази – Ukrainian" lang="uk" hreflang="uk" data-title="Ізомерази" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%95%B0%E6%A7%8B%E9%85%B6" title="異構酶 – Chinese" lang="zh" hreflang="zh" data-title="異構酶" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q118026#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Isomerase" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Isomerase" rel="discussion" 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<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">Class of enzymes which convert a molecule between isomeric forms</div> <p>In <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, <b>isomerases</b> are a general class of <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that convert a molecule from one <a href="/wiki/Isomer" title="Isomer">isomer</a> to another. Isomerases facilitate intramolecular rearrangements in which <a href="/wiki/Chemical_bond" title="Chemical bond">bonds</a> are <a href="/wiki/Bond_cleavage" title="Bond cleavage">broken</a> and formed. The general form of such a reaction is as follows: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {A-B}}\quad {\xrightarrow[{\text{ isomerase }}]{}}\quad {\ce {B-A}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>B</mtext> </mrow> <mspace width="1em" /> <mrow class="MJX-TeXAtom-ORD"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <mtext> isomerase </mtext> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em" /> </munderover> </mrow> <mspace width="1em" /> <mrow class="MJX-TeXAtom-ORD"> <mtext>B</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>A</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {A-B}}\quad {\xrightarrow[{\text{ isomerase }}]{}}\quad {\ce {B-A}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/3e7114e4d3961ea355ca13869f9ea72fc1b38e08" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.767ex; margin-top: -0.452ex; margin-bottom: -0.571ex; width:24.394ex; height:4.676ex;" alt="{\displaystyle {\ce {A-B}}\quad {\xrightarrow[{\text{ isomerase }}]{}}\quad {\ce {B-A}}}"></span></dd></dl> <p>There is only one <a href="/wiki/Enzyme_substrate_(biology)" class="mw-redirect" title="Enzyme substrate (biology)">substrate</a> yielding one product. This product has the same <a href="/wiki/Chemical_formula" title="Chemical formula">molecular formula</a> as the substrate but differs in bond connectivity or spatial arrangement. Isomerases <a href="/wiki/Catalyze" class="mw-redirect" title="Catalyze">catalyze</a> reactions across many biological processes, such as in <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> and <a href="/wiki/Carbohydrate_metabolism" title="Carbohydrate metabolism">carbohydrate metabolism</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Isomerization">Isomerization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=1" title="Edit section: Isomerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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:204px;max-width:204px"><div class="trow"><div class="theader">Examples of isomers</div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Hexane_isomers.svg" class="mw-file-description"><img alt="zig-zag models of hexane and four isomers" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Hexane_isomers.svg/200px-Hexane_isomers.svg.png" decoding="async" width="200" height="215" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Hexane_isomers.svg/300px-Hexane_isomers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Hexane_isomers.svg/400px-Hexane_isomers.svg.png 2x" data-file-width="330" data-file-height="354" /></a></span></div><div class="thumbcaption">The structural isomers of hexane</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Cis-trans_example.svg" class="mw-file-description"><img alt="zig-zag model of cis-2-butene vs trans-2-butene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/200px-Cis-trans_example.svg.png" decoding="async" width="200" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/300px-Cis-trans_example.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Cis-trans_example.svg/400px-Cis-trans_example.svg.png 2x" data-file-width="540" data-file-height="230" /></a></span></div><div class="thumbcaption">Cis-2-butene and Trans-2-butene</div></div></div><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Epimers-Glucose_Mannose.png" class="mw-file-description"><img alt="projection of D-glucose and D-mannose" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Epimers-Glucose_Mannose.png/200px-Epimers-Glucose_Mannose.png" decoding="async" width="200" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/c/ca/Epimers-Glucose_Mannose.png 1.5x" data-file-width="255" data-file-height="223" /></a></span></div><div class="thumbcaption">Epimers: D-glucose and D-mannose</div></div></div></div></div> <p>Isomerases <a href="/wiki/Catalysis" title="Catalysis">catalyze</a> changes within one molecule.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They convert one isomer to another, meaning that the end product has the same molecular formula but a different physical structure. <a href="/wiki/Isomer" title="Isomer">Isomers</a> themselves exist in many varieties but can generally be classified as <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a> or <a href="/wiki/Stereoisomerism" title="Stereoisomerism">stereoisomers</a>. Structural isomers have a different ordering of bonds and/or different bond connectivity from one another, as in the case of <a href="/wiki/Hexane" title="Hexane">hexane</a> and its four other isomeric forms (<a href="/wiki/2-methylpentane" class="mw-redirect" title="2-methylpentane">2-methylpentane</a>, <a href="/wiki/3-methylpentane" class="mw-redirect" title="3-methylpentane">3-methylpentane</a>, <a href="/wiki/2,2-dimethylbutane" class="mw-redirect" title="2,2-dimethylbutane">2,2-dimethylbutane</a>, and <a href="/wiki/2,3-dimethylbutane" class="mw-redirect" title="2,3-dimethylbutane">2,3-dimethylbutane</a>). </p><p>Stereoisomers have the same ordering of individual bonds and the same connectivity but the three-dimensional arrangement of bonded atoms differ. For example, <a href="/wiki/2-butene" class="mw-redirect" title="2-butene">2-butene</a> exists in two isomeric forms: <i>cis</i>-2-butene and <i>trans</i>-2-butene.<sup id="cite_ref-gold_2-0" class="reference"><a href="#cite_note-gold-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The sub-categories of isomerases containing racemases, epimerases and cis-trans isomers are examples of enzymes catalyzing the interconversion of stereoisomers. Intramolecular lyases, oxidoreductases and transferases catalyze the interconversion of structural isomers. </p><p>The prevalence of each isomer in nature depends in part on the <a href="/wiki/Activation_energy" title="Activation energy">isomerization energy</a>, the difference in energy between isomers. Isomers close in energy can interconvert easily and are often seen in comparable proportions. The isomerization energy, for example, for converting from a stable <i>cis</i> isomer to the less stable <i>trans</i> isomer is greater than for the reverse reaction, explaining why in the absence of isomerases or an outside energy source such as <a href="/wiki/Ultraviolet_radiation" class="mw-redirect" title="Ultraviolet radiation">ultraviolet radiation</a> a given <i>cis</i> isomer tends to be present in greater amounts than the <i>trans</i> isomer. Isomerases can increase the <a href="/wiki/Reaction_rate" title="Reaction rate">reaction rate</a> by lowering the isomerization energy.<sup id="cite_ref-organic_3-0" class="reference"><a href="#cite_note-organic-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Calculating isomerase <a href="/wiki/Enzyme_kinetics" title="Enzyme kinetics">kinetics</a> from experimental data can be more difficult than for other enzymes because the use of <a href="/wiki/Reaction_progress_kinetic_analysis" title="Reaction progress kinetic analysis">product inhibition experiments</a> is impractical.<sup id="cite_ref-kinetics_4-0" class="reference"><a href="#cite_note-kinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> That is, isomerization is not an <a href="/wiki/Irreversible_process" title="Irreversible process">irreversible reaction</a> since a reaction vessel will contain one substrate and one product so the typical simplified model for calculating <a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">reaction kinetics</a> does not hold. There are also practical difficulties in determining the <a href="/wiki/Rate-determining_step" title="Rate-determining step">rate-determining step</a> at high concentrations in a single isomerization. Instead, tracer perturbation can overcome these technical difficulties if there are two forms of the unbound enzyme. This technique uses <a href="/wiki/Isotopic_labeling" title="Isotopic labeling">isotope exchange</a> to measure indirectly the <a href="/wiki/Reversible_reaction" title="Reversible reaction">interconversion</a> of the free enzyme between its two forms. The radiolabeled substrate and product <a href="/wiki/Diffusion" title="Diffusion">diffuse</a> in a time-dependent manner. When the system reaches <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> the addition of unlabeled substrate perturbs or unbalances it. As equilibrium is established again, the radiolabeled substrate and product are tracked to determine energetic information.<sup id="cite_ref-proline_5-0" class="reference"><a href="#cite_note-proline-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The earliest use of this technique elucidated the kinetics and <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">mechanism</a> underlying the action of <a href="/wiki/Phosphoglucomutase" title="Phosphoglucomutase">phosphoglucomutase</a>, favoring the model of indirect transfer of <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> with one <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediate</a> and the direct transfer of <a href="/wiki/Glucose" title="Glucose">glucose</a>.<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> This technique was then adopted to study the profile of <a href="/wiki/Proline_racemase" title="Proline racemase">proline racemase</a> and its two states: the form which isomerizes L-<a href="/wiki/Proline" title="Proline">proline</a> and the other for D-proline. At high concentrations it was shown that the <a href="/wiki/Transition_state" title="Transition state">transition state</a> in this interconversion is <a href="/wiki/Rate-determining_step" title="Rate-determining step">rate-limiting</a> and that these enzyme forms may differ just in the <a href="/wiki/Protonation" title="Protonation">protonation</a> at the <a href="/wiki/Acid" title="Acid">acidic</a> and <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> <a href="/wiki/Functional_group" title="Functional group">groups</a> of the <a href="/wiki/Active_site" title="Active site">active site</a>.<sup id="cite_ref-proline_5-1" class="reference"><a href="#cite_note-proline-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=2" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Generally, "the names of isomerases are formed as "<i>substrate</i> isomerase" (for example, <a href="/wiki/Enoyl_CoA_isomerase" title="Enoyl CoA isomerase">enoyl CoA isomerase</a>), or as "<i>substrate</i> <i>type of isomerase</i>" (for example, <a href="/wiki/Phosphoglucomutase" title="Phosphoglucomutase">phosphoglucomutase</a>)."<sup id="cite_ref-essential_7-0" class="reference"><a href="#cite_note-essential-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=3" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Enzyme-catalyzed reactions each have a uniquely assigned classification number. Isomerase-catalyzed reactions have their own <a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> category: EC 5.<sup id="cite_ref-nomenclature_8-0" class="reference"><a href="#cite_note-nomenclature-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Isomerases are further classified into six subclasses: </p> <div class="mw-heading mw-heading3"><h3 id="Racemases,_epimerases"><span id="Racemases.2C_epimerases"></span>Racemases, epimerases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=4" title="Edit section: Racemases, epimerases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This category (EC 5.1) includes (<a href="/wiki/Racemase" class="mw-redirect" title="Racemase">racemases</a>) and <a href="/wiki/Epimerase" class="mw-redirect" title="Epimerase">epimerases</a>). These isomerases invert <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> at the target <a href="/wiki/Stereocenter" title="Stereocenter">chiral carbon</a>. <a href="/wiki/Epimerase_and_racemase" title="Epimerase and racemase">Racemases</a> act upon molecules with one chiral carbon for inversion of stereochemistry, whereas epimerases target molecules with multiple chiral carbons and act upon one of them. A molecule with only one chiral carbon has two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomeric</a> forms, such as <a href="/wiki/Serine" title="Serine">serine</a> having the isoforms D-serine and L-serine differing only in the <a href="/wiki/Absolute_configuration" title="Absolute configuration">absolute configuration</a> about the chiral carbon. A molecule with multiple chiral carbons has two forms at each chiral carbon. Isomerization at one chiral carbon of several yields <a href="/wiki/Epimer" title="Epimer">epimers</a>, which differ from one another in absolute configuration at just one chiral carbon.<sup id="cite_ref-gold_2-1" class="reference"><a href="#cite_note-gold-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> For example, D-<a href="/wiki/Glucose" title="Glucose">glucose</a> and D-<a href="/wiki/Mannose" title="Mannose">mannose</a> differ in configuration at just one chiral carbon. This class is further broken down by the group the enzyme acts upon: </p> <table class="wikitable"> <caption>Racemases and epimerases: </caption> <tbody><tr> <th>EC number</th> <th>Description</th> <th>Examples </th></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.1.1" title="Category:EC 5.1.1">EC 5.1.1</a></td> <td>Acting on Amino Acids and Derivative</td> <td><a href="/wiki/Alanine_racemase" title="Alanine racemase">alanine racemase</a>, <a href="/wiki/Methionine_racemase" title="Methionine racemase">methionine racemase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.1.2" title="Category:EC 5.1.2">EC 5.1.2</a></td> <td>Acting on Hydroxy Acids and Derivatives</td> <td><a href="/wiki/Lactate_racemase" title="Lactate racemase">lactate racemase</a>, <a href="/wiki/Tartrate_epimerase" title="Tartrate epimerase">tartrate epimerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.1.3" title="Category:EC 5.1.3">EC 5.1.3</a></td> <td>Acting on Carbohydrates and Derivatives</td> <td><a href="/wiki/Ribulose-phosphate_3-epimerase" class="mw-redirect" title="Ribulose-phosphate 3-epimerase">ribulose-phosphate 3-epimerase</a>, <a href="/wiki/UDP-glucose_4-epimerase" title="UDP-glucose 4-epimerase">UDP-glucose 4-epimerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.1.99" title="Category:EC 5.1.99">EC 5.1.99</a></td> <td>Acting on Other Compounds</td> <td><a href="/wiki/Methylmalonyl_CoA_epimerase" title="Methylmalonyl CoA epimerase">methylmalonyl CoA epimerase</a>, <a href="/wiki/Hydantoin_racemase" title="Hydantoin racemase">hydantoin racemase</a> </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Cis-trans_isomerases">Cis-trans isomerases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=5" title="Edit section: Cis-trans isomerases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This category (EC 5.2) includes enzymes that catalyze the isomerization of <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">cis-trans isomers</a>. <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">Alkenes</a> and <a href="/wiki/Cycloalkanes" class="mw-redirect" title="Cycloalkanes">cycloalkanes</a> may have cis-trans stereoisomers. These isomers are not distinguished by <a href="/wiki/Absolute_configuration" title="Absolute configuration">absolute configuration</a> but rather by the position of substituent groups relative to a plane of reference, as across a double bond or relative to a ring structure. <i>Cis</i> isomers have substituent groups on the same side and <i>trans</i> isomers have groups on opposite sides.<sup id="cite_ref-gold_2-2" class="reference"><a href="#cite_note-gold-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>This category is not broken down any further. All entries presently include: </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Proline-cis-trans-isomerisation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Proline-cis-trans-isomerisation.svg/220px-Proline-cis-trans-isomerisation.svg.png" decoding="async" width="220" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Proline-cis-trans-isomerisation.svg/330px-Proline-cis-trans-isomerisation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Proline-cis-trans-isomerisation.svg/440px-Proline-cis-trans-isomerisation.svg.png 2x" data-file-width="512" data-file-height="197" /></a><figcaption>Conversion mediated by peptidylprolyl isomerase (PPIase).</figcaption></figure> <table class="wikitable"> <caption>Cis-trans isomerases: </caption> <tbody><tr> <th>EC number</th> <th>Examples </th></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.1</a></td> <td><a href="/wiki/Maleate_isomerase" title="Maleate isomerase">Maleate isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.2</a></td> <td><a href="/wiki/Maleylacetoacetate_isomerase" title="Maleylacetoacetate isomerase">Maleylacetoacetate isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.4</a></td> <td><a href="/wiki/Maleylpyruvate_isomerase" title="Maleylpyruvate isomerase">Maleylpyruvate isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.5</a></td> <td><a href="/wiki/Linoleate_isomerase" title="Linoleate isomerase">Linoleate isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.6</a></td> <td><a href="/wiki/Furylfuramide_isomerase" title="Furylfuramide isomerase">Furylfuramide isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.8</a></td> <td><a href="/wiki/Peptidylprolyl_isomerase_A" title="Peptidylprolyl isomerase A">Peptidylprolyl isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.9</a></td> <td><a href="/wiki/Farnesol_2-isomerase" title="Farnesol 2-isomerase">Farnesol 2-isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.10</a></td> <td><a href="/wiki/2-chloro-4-carboxymethylenebut-2-en-1,4-olide_isomerase" title="2-chloro-4-carboxymethylenebut-2-en-1,4-olide isomerase">2-chloro-4-carboxymethylenebut-2-en-1,4-olide isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.12</a></td> <td><a href="/wiki/Zeta-carotene_isomerase" title="Zeta-carotene isomerase">Zeta-carotene isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.13</a></td> <td><a href="/wiki/Prolycopene_isomerase" title="Prolycopene isomerase">Prolycopene isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.2.1" title="Category:EC 5.2.1">EC 5.2.1.14</a></td> <td><a href="/wiki/Beta-carotene_isomerase" title="Beta-carotene isomerase">Beta-carotene isomerase</a> </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_oxidoreductases">Intramolecular oxidoreductases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=6" title="Edit section: Intramolecular oxidoreductases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This category (EC 5.3) includes <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductases</a>. These isomerases catalyze the transfer of <a href="/wiki/Electron" title="Electron">electrons</a> from one part of the molecule to another. In other words, they catalyze the <a href="/wiki/Redox" title="Redox">oxidation</a> of one part of the molecule and the concurrent reduction of another part.<sup id="cite_ref-nomenclature_8-1" class="reference"><a href="#cite_note-nomenclature-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Sub-categories of this class are: </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphoribosylanthranilate_isomerase.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Phosphoribosylanthranilate_isomerase.jpg/220px-Phosphoribosylanthranilate_isomerase.jpg" decoding="async" width="220" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Phosphoribosylanthranilate_isomerase.jpg/330px-Phosphoribosylanthranilate_isomerase.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Phosphoribosylanthranilate_isomerase.jpg/440px-Phosphoribosylanthranilate_isomerase.jpg 2x" data-file-width="539" data-file-height="134" /></a><figcaption>reaction catalyzed by phosphoribosylanthranilate isomerase</figcaption></figure> <table class="wikitable"> <caption>Intramolecular oxidoreductases: </caption> <tbody><tr> <th>EC number</th> <th>Description</th> <th>Examples </th></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.3.1" title="Category:EC 5.3.1">EC 5.3.1</a></td> <td>Interconverting Aldoses and Ketoses</td> <td><a href="/wiki/Triose-phosphate_isomerase" class="mw-redirect" title="Triose-phosphate isomerase">Triose-phosphate isomerase</a>, <a href="/wiki/Ribose-5-phosphate_isomerase" title="Ribose-5-phosphate isomerase">Ribose-5-phosphate isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.3.2" title="Category:EC 5.3.2">EC 5.3.2</a></td> <td>Interconverting Keto- and Enol-Groups</td> <td><a href="/wiki/Phenylpyruvate_tautomerase" title="Phenylpyruvate tautomerase">Phenylpyruvate tautomerase</a>, <a href="/wiki/Oxaloacetate_tautomerase" title="Oxaloacetate tautomerase">Oxaloacetate tautomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.3.3" title="Category:EC 5.3.3">EC 5.3.3</a></td> <td>Transposing C=C Double Bonds</td> <td><a href="/wiki/Steroid_Delta-isomerase" title="Steroid Delta-isomerase">Steroid Delta-isomerase</a>, <a href="/wiki/L-dopachrome_isomerase" title="L-dopachrome isomerase">L-dopachrome isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.3.4" title="Category:EC 5.3.4">EC 5.3.4</a></td> <td>Transposing S-S Bonds</td> <td><a href="/wiki/Protein_disulfide-isomerase" title="Protein disulfide-isomerase">Protein disulfide-isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.3.99" title="Category:EC 5.3.99">EC 5.3.99</a></td> <td>Other Intramolecular Oxidoreductases</td> <td><a href="/wiki/Prostaglandin-D_synthase" title="Prostaglandin-D synthase">Prostaglandin-D synthase</a>, <a href="/wiki/Allene-oxide_cyclase" class="mw-redirect" title="Allene-oxide cyclase">Allene-oxide cyclase</a> </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_transferases">Intramolecular transferases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=7" title="Edit section: Intramolecular transferases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This category (EC 5.4) includes intramolecular <a href="/wiki/Transferase" title="Transferase">transferases</a> (<a href="/wiki/Mutase" title="Mutase">mutases</a>). These isomerases catalyze the transfer of <a href="/wiki/Functional_group" title="Functional group">functional groups</a> from one part of a molecule to another.<sup id="cite_ref-nomenclature_8-2" class="reference"><a href="#cite_note-nomenclature-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Phosphotransferases (EC 5.4.2) were categorized as transferases (EC 2.7.5) with regeneration of donors until 1983.<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> This sub-class can be broken down according to the functional group the enzyme transfers: </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:PEP_to_PPR.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PEP_to_PPR.png/220px-PEP_to_PPR.png" decoding="async" width="220" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PEP_to_PPR.png/330px-PEP_to_PPR.png 1.5x, //upload.wikimedia.org/wikipedia/commons/3/3f/PEP_to_PPR.png 2x" data-file-width="332" data-file-height="120" /></a><figcaption>reaction catalyzed by phosphoenolpyruvate mutase</figcaption></figure> <table class="wikitable"> <caption>Intramolecular transferases: </caption> <tbody><tr> <th>EC number</th> <th>Description</th> <th>Examples </th></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.4.1" title="Category:EC 5.4.1">EC 5.4.1</a></td> <td>Transferring Acyl Groups</td> <td><a href="/wiki/Lysolecithin_acylmutase" title="Lysolecithin acylmutase">Lysolecithin acylmutase</a>, <a href="/wiki/Precorrin-8X_methylmutase" title="Precorrin-8X methylmutase">Precorrin-8X methylmutase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.4.2" title="Category:EC 5.4.2">EC 5.4.2</a></td> <td>Phosphotransferases (Phosphomutases)</td> <td><a href="/wiki/Phosphoglucomutase" title="Phosphoglucomutase">Phosphoglucomutase</a>, <a href="/wiki/Phosphopentomutase" title="Phosphopentomutase">Phosphopentomutase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.4.3" title="Category:EC 5.4.3">EC 5.4.3</a></td> <td>Transferring Amino Groups</td> <td><a href="/wiki/Beta-lysine_5,6-aminomutase" title="Beta-lysine 5,6-aminomutase">Beta-lysine 5,6-aminomutase</a>, <a href="/wiki/Tyrosine_2,3-aminomutase" title="Tyrosine 2,3-aminomutase">Tyrosine 2,3-aminomutase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.4.4" title="Category:EC 5.4.4">EC 5.4.4</a></td> <td>Transferring hydroxy groups</td> <td><a href="/wiki/(hydroxyamino)benzene_mutase" title="(hydroxyamino)benzene mutase">(hydroxyamino)benzene mutase</a>, <a href="/wiki/Isochorismate_synthase" title="Isochorismate synthase">Isochorismate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.4.99" title="Category:EC 5.4.99">EC 5.4.99</a></td> <td>Transferring Other Groups</td> <td><a href="/wiki/Methylaspartate_mutase" title="Methylaspartate mutase">Methylaspartate mutase</a>, <a href="/wiki/Chorismate_mutase" title="Chorismate mutase">Chorismate mutase</a> </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_lyases">Intramolecular lyases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=8" title="Edit section: Intramolecular lyases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This category (EC 5.5) includes intramolecular <a href="/wiki/Lyase" title="Lyase">lyases</a>. These enzymes catalyze "reactions in which a group can be regarded as eliminated from one part of a molecule, leaving a double bond, while remaining <a href="/wiki/Covalent_bond" title="Covalent bond">covalently</a> attached to the molecule."<sup id="cite_ref-nomenclature_8-3" class="reference"><a href="#cite_note-nomenclature-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Some of these catalyzed reactions involve the breaking of a ring structure. </p><p>This category is not broken down any further. All entries presently include: </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ent-CDP_synthase_reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ent-CDP_synthase_reaction.png/220px-Ent-CDP_synthase_reaction.png" decoding="async" width="220" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ent-CDP_synthase_reaction.png/330px-Ent-CDP_synthase_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Ent-CDP_synthase_reaction.png/440px-Ent-CDP_synthase_reaction.png 2x" data-file-width="2057" data-file-height="348" /></a><figcaption>reaction catalyzed by ent-Copalyl diphosphate synthase</figcaption></figure> <table class="wikitable"> <caption>Intramolecular lyases: </caption> <tbody><tr> <th>EC number</th> <th>Examples </th></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.1</a></td> <td><a href="/wiki/Muconate_cycloisomerase" class="mw-redirect" title="Muconate cycloisomerase">Muconate cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.2</a></td> <td><a href="/wiki/3-carboxy-cis,cis-muconate_cycloisomerase" title="3-carboxy-cis,cis-muconate cycloisomerase">3-carboxy-cis,cis-muconate cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.3</a></td> <td><a href="/wiki/Tetrahydroxypteridine_cycloisomerase" title="Tetrahydroxypteridine cycloisomerase">Tetrahydroxypteridine cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.4</a></td> <td><a href="/wiki/Inositol-3-phosphate_synthase" title="Inositol-3-phosphate synthase">Inositol-3-phosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.5</a></td> <td><a href="/wiki/Carboxy-cis,cis-muconate_cyclase" title="Carboxy-cis,cis-muconate cyclase">Carboxy-cis,cis-muconate cyclase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.6</a></td> <td><a href="/wiki/Chalcone_isomerase" title="Chalcone isomerase">Chalcone isomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.7</a></td> <td><a href="/wiki/Chloromuconate_cycloisomerase" title="Chloromuconate cycloisomerase">Chloromuconate cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.8</a></td> <td><a href="/wiki/Bornyl_diphosphate_synthase" title="Bornyl diphosphate synthase">(+)-bornyl diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.9</a></td> <td><a href="/wiki/Cycloeucalenol_cycloisomerase" title="Cycloeucalenol cycloisomerase">Cycloeucalenol cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.10</a></td> <td><a href="/wiki/Alpha-pinene-oxide_decyclase" title="Alpha-pinene-oxide decyclase">Alpha-pinene-oxide decyclase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.11</a></td> <td><a href="/wiki/Dichloromuconate_cycloisomerase" title="Dichloromuconate cycloisomerase">Dichloromuconate cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.12</a></td> <td><a href="/wiki/Copalyl_diphosphate_synthase" title="Copalyl diphosphate synthase">Copalyl diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.13</a></td> <td><a href="/wiki/Ent-copalyl_diphosphate_synthase" class="mw-redirect" title="Ent-copalyl diphosphate synthase">Ent-copalyl diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.14</a></td> <td><a href="/wiki/Syn-copalyl-diphosphate_synthase" title="Syn-copalyl-diphosphate synthase">Syn-copalyl-diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.15</a></td> <td><a href="/wiki/Terpentedienyl-diphosphate_synthase" title="Terpentedienyl-diphosphate synthase">Terpentedienyl-diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.16</a></td> <td><a href="/wiki/Halimadienyl-diphosphate_synthase" title="Halimadienyl-diphosphate synthase">Halimadienyl-diphosphate synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.17</a></td> <td><a href="/wiki/(S)-beta-macrocarpene_synthase" title="(S)-beta-macrocarpene synthase">(S)-beta-macrocarpene synthase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.18</a></td> <td><a href="/wiki/Lycopene_epsilon-cyclase" title="Lycopene epsilon-cyclase">Lycopene epsilon-cyclase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.19</a></td> <td><a href="/wiki/Lycopene_beta-cyclase" title="Lycopene beta-cyclase">Lycopene beta-cyclase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.20</a></td> <td><a href="/wiki/Prosolanapyrone-III_cycloisomerase" title="Prosolanapyrone-III cycloisomerase">Prosolanapyrone-III cycloisomerase</a> </td></tr> <tr> <td align=""><a href="/wiki/Category:EC_5.5.1" title="Category:EC 5.5.1">EC 5.5.1.n1</a></td> <td>D-ribose pyranase </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Mechanisms_of_isomerases">Mechanisms of isomerases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=9" title="Edit section: Mechanisms of isomerases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Ring_expansion_and_contraction_via_tautomers">Ring expansion and contraction via tautomers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=10" title="Edit section: Ring expansion and contraction via tautomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phosphoglucose_Isomerase_Mechanism.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/2/2c/Phosphoglucose_Isomerase_Mechanism.jpg/220px-Phosphoglucose_Isomerase_Mechanism.jpg" decoding="async" width="220" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/2/2c/Phosphoglucose_Isomerase_Mechanism.jpg/330px-Phosphoglucose_Isomerase_Mechanism.jpg 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/2/2c/Phosphoglucose_Isomerase_Mechanism.jpg/440px-Phosphoglucose_Isomerase_Mechanism.jpg 2x" data-file-width="1796" data-file-height="1264" /></a><figcaption>The isomerization of glucose-6-phosphate by glucose-6-phosphate isomerase</figcaption></figure> <p>A classic example of ring opening and contraction is the isomerization of <a href="/wiki/Glucose" title="Glucose">glucose</a> (an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> with a six-membered ring) to <a href="/wiki/Fructose" title="Fructose">fructose</a> (a <a href="/wiki/Ketone" title="Ketone">ketone</a> with a five-membered ring). The conversion of D-glucose-6-phosphate to D-fructose-6-phosphate is catalyzed by <a href="/wiki/Glucose-6-phosphate_isomerase" title="Glucose-6-phosphate isomerase">glucose-6-phosphate isomerase</a>, an intramolecular <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductase</a>. The overall reaction involves the opening of the ring to form an aldose via <a href="/wiki/Acid_catalysis" title="Acid catalysis">acid/base catalysis</a> and the subsequent formation of a cis-endiol intermediate. A ketose is then formed and the ring is closed again. </p><p>Glucose-6-phosphate first binds to the <a href="/wiki/Active_site" title="Active site">active site</a> of the isomerase. The isomerase opens the ring: its <a href="/wiki/Histidine" title="Histidine">His388</a> residue <a href="/wiki/Protonation" title="Protonation">protonates</a> the oxygen on the glucose ring (and thereby breaking the O5-C1 bond) in conjunction with <a href="/wiki/Lysine" title="Lysine">Lys518</a> deprotonating the C1 <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> oxygen. The ring opens to form a straight-chain <a href="/wiki/Aldose" title="Aldose">aldose</a> with an acidic C2 proton. The C3-C4 bond rotates and <a href="/wiki/Glutamic_acid" title="Glutamic acid">Glu357</a> (assisted by His388) depronates C2 to form a double bond between C1 and C2. A <a href="/wiki/Enol" title="Enol">cis-endiol</a> intermediate is created and the C1 oxygen is protonated by the catalytic residue, accompanied by the deprotonation of the endiol C2 oxygen. The straight-chain <a href="/wiki/Ketose" title="Ketose">ketose</a> is formed. To close the fructose ring, the reverse of ring opening occurs and the ketose is protonated.<sup id="cite_ref-phosphoglucose_10-0" class="reference"><a href="#cite_note-phosphoglucose-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Epimerization">Epimerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=11" title="Edit section: Epimerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ribulose-phosphate_3-epimerase_reaction.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/2/2e/Ribulose-phosphate_3-epimerase_reaction.jpg/220px-Ribulose-phosphate_3-epimerase_reaction.jpg" decoding="async" width="220" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/2/2e/Ribulose-phosphate_3-epimerase_reaction.jpg/330px-Ribulose-phosphate_3-epimerase_reaction.jpg 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/2/2e/Ribulose-phosphate_3-epimerase_reaction.jpg/440px-Ribulose-phosphate_3-epimerase_reaction.jpg 2x" data-file-width="1290" data-file-height="292" /></a><figcaption>The conversion of ribulose-5-phosphate to xylulose-5-phosphate</figcaption></figure> <p>An example of epimerization is found in the Calvin cycle when D-ribulose-5-phosphate is converted into D-xylulose-5-phosphate by <a href="/wiki/Ribulose-phosphate_3-epimerase" class="mw-redirect" title="Ribulose-phosphate 3-epimerase">ribulose-phosphate 3-epimerase</a>. The substrate and product differ only in <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> at the third carbon in the chain. The underlying mechanism involves the deprotonation of that third carbon to form a reactive <a href="/wiki/Enol" title="Enol">enolate</a> intermediate. The enzyme's active site contains two <a href="/wiki/Aspartate" class="mw-redirect" title="Aspartate">Asp</a> residues. After the substrate binds to the enzyme, the first Asp deprotonates the third carbon from one side of the molecule. This leaves a planar <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">sp<sup>2</sup>-hybridized</a> intermediate. The second Asp is located on the opposite side of the active side and it protonates the molecule, effectively adding a proton from the back side. These coupled steps invert stereochemistry at the third carbon.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_transfer">Intramolecular transfer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=12" title="Edit section: Intramolecular transfer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Chorismate_mutase_mechanism.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/7/7d/Chorismate_mutase_mechanism.gif/220px-Chorismate_mutase_mechanism.gif" decoding="async" width="220" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/7/7d/Chorismate_mutase_mechanism.gif/330px-Chorismate_mutase_mechanism.gif 1.5x, //upload.wikimedia.org/wikipedia/en/7/7d/Chorismate_mutase_mechanism.gif 2x" data-file-width="363" data-file-height="289" /></a><figcaption>A proposed mechanism for chorismate mutase. Clark, T., Stewart, J.D. and Ganem, B. Transition-state analogue inhibitors of chlorismate mutase. Tetrahedron 46 (1990) 731–748. © IUBMB 2001</figcaption></figure> <p><a href="/wiki/Chorismate_mutase" title="Chorismate mutase">Chorismate mutase</a> is an intramolecular transferase and it catalyzes the conversion of <a href="/wiki/Chorismic_acid" title="Chorismic acid">chorismate</a> to <a href="/wiki/Prephenic_acid" title="Prephenic acid">prephenate</a>, used as a precursor for <a href="/wiki/Tyrosine" title="Tyrosine">L-tyrosine</a> and <a href="/wiki/Phenylalanine" title="Phenylalanine">L-phenylalanine</a> in some plants and bacteria. This reaction is a <a href="/wiki/Claisen_rearrangement" title="Claisen rearrangement">Claisen rearrangement</a> that can proceed with or without the isomerase, though the rate increases 10<sup>6</sup> fold in the presence of chorismate mutase. The reaction goes through a <a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">chair</a> <a href="/wiki/Transition_state" title="Transition state">transition state</a> with the substrate in a trans-diaxial position.<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> Experimental evidence indicates that the isomerase selectively binds the chair transition state, though the exact mechanism of <a href="/wiki/Catalysis" title="Catalysis">catalysis</a> is not known. It is thought that this binding stabilizes the transition state through electrostatic effects, accounting for the dramatic increase in the reaction rate in the presence of the mutase or upon addition of a specifically-placed cation in the active site.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Intramolecular_oxidoreduction">Intramolecular oxidoreduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=13" title="Edit section: Intramolecular oxidoreduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:IPP_isomerase_mechanism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/IPP_isomerase_mechanism.png/220px-IPP_isomerase_mechanism.png" decoding="async" width="220" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/IPP_isomerase_mechanism.png/330px-IPP_isomerase_mechanism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/IPP_isomerase_mechanism.png/440px-IPP_isomerase_mechanism.png 2x" data-file-width="824" data-file-height="267" /></a><figcaption>Conversion by IPP isomerase</figcaption></figure> <p><a href="/wiki/Isopentenyl-diphosphate_delta_isomerase" title="Isopentenyl-diphosphate delta isomerase">Isopentenyl-diphosphate delta isomerase</a> type I (also known as IPP isomerase) is seen in <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> synthesis and in particular it catalyzes the conversion of <a href="/wiki/Isopentenyl_diphosphate" class="mw-redirect" title="Isopentenyl diphosphate">isopentenyl diphosphate</a> (IPP) to <a href="/wiki/Dimethylallyl_diphosphate" class="mw-redirect" title="Dimethylallyl diphosphate">dimethylallyl diphosphate</a> (DMAPP). In this isomerization reaction a stable carbon-carbon double bond is rearranged top create a highly <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> <a href="/wiki/Allylic_rearrangement" title="Allylic rearrangement">allylic isomer</a>. IPP isomerase catalyzes this reaction by the <a href="/wiki/Stereoselectivity" title="Stereoselectivity">stereoselective</a> <a href="/wiki/Antarafacial" class="mw-redirect" title="Antarafacial">antarafacial</a> transposition of a single proton. The <a href="/wiki/Double_bond" title="Double bond">double bond</a> is protonated at C4 to form a tertiary <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> intermediate at C3. The adjacent carbon, C2, is deprotonated from the opposite face to yield a double bond.<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> In effect, the double bond is shifted over. </p> <div class="mw-heading mw-heading2"><h2 id="The_role_of_isomerase_in_human_disease">The role of isomerase in human disease</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=14" title="Edit section: The role of isomerase in human disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isomerase plays a role in human disease. Deficiencies of this enzyme can cause disorders in humans. </p> <div class="mw-heading mw-heading3"><h3 id="Phosphohexose_isomerase_deficiency">Phosphohexose isomerase deficiency</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=15" title="Edit section: Phosphohexose isomerase deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phosphohexose Isomerase Deficiency (PHI) is also known as phosphoglucose isomerase deficiency or <a href="/w/index.php?title=Glucose-6-phosphate_isomerase_deficiency&action=edit&redlink=1" class="new" title="Glucose-6-phosphate isomerase deficiency (page does not exist)">Glucose-6-phosphate isomerase deficiency</a>, and is a hereditary enzyme deficiency. PHI is the second most frequent <a href="/w/index.php?title=Erthoenzyopathy&action=edit&redlink=1" class="new" title="Erthoenzyopathy (page does not exist)">erthoenzyopathy</a> in <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> besides <a href="/wiki/Pyruvate_kinase_deficiency" title="Pyruvate kinase deficiency">pyruvate kinase deficiency</a>, and is associated with non-spherocytic haemolytic anaemia of variable severity.<sup id="cite_ref-GDI_15-0" class="reference"><a href="#cite_note-GDI-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hemolytic_Anemia_16-0" class="reference"><a href="#cite_note-Hemolytic_Anemia-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> This disease is centered on the glucose-6-phosphate protein. This protein can be found in the secretion of some cancer cells.<sup id="cite_ref-PHI_Deficiency_17-0" class="reference"><a href="#cite_note-PHI_Deficiency-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> PHI is the result of a dimeric enzyme that catalyses the reversible interconversion of fructose-6-phosphate and gluose-6-phosphate.<sup id="cite_ref-GDI_15-1" class="reference"><a href="#cite_note-GDI-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>PHI is a very rare disease with only 50 cases reported in literature to date.<sup id="cite_ref-GDI_15-2" class="reference"><a href="#cite_note-GDI-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Diagnosis is made on the basis of the clinical picture in association with biochemical studies revealing erythrocyte GPI deficiency (between 7 and 60% of normal) and identification of a mutation in the GPI gene by molecular analysis.<sup id="cite_ref-GDI_15-3" class="reference"><a href="#cite_note-GDI-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The deficiency of phosphohexose isomerase can lead to a condition referred to as <a href="/w/index.php?title=Hemolytic_syndrome&action=edit&redlink=1" class="new" title="Hemolytic syndrome (page does not exist)">hemolytic syndrome</a>. As in humans, the hemolytic syndrome, which is characterized by a diminished erythrocyte number, lower hematocrit, lower <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a>, higher number of reticulocytes and plasma bilirubin concentration, as well as increased liver- and spleen-somatic indices, was exclusively manifested in homozygous mutants.<sup id="cite_ref-Hemolytic_Anemia_16-1" class="reference"><a href="#cite_note-Hemolytic_Anemia-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Triosephosphate_isomerase_deficiency">Triosephosphate isomerase deficiency</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=16" title="Edit section: Triosephosphate isomerase deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The disease referred to as triosephosphate isomerase deficiency (TPI), is a severe autosomal recessive inherited multisystem disorder of <a href="/w/index.php?title=Glycolytic_metabolism&action=edit&redlink=1" class="new" title="Glycolytic metabolism (page does not exist)">glycolytic metabolism</a>.<sup id="cite_ref-Orphanet_18-0" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> It is characterized by hemolytic anemia and neurodegeneration, and is caused by anaerobic metabolic dysfunction. This dysfunction results from a missense mutation that effects the encoded TPI protein.<sup id="cite_ref-TPI_Deficiency_19-0" class="reference"><a href="#cite_note-TPI_Deficiency-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The most common mutation is the substitution of gene, Glu104Asp, which produces the most severe <a href="/wiki/Phenotype" title="Phenotype">phenotype</a>, and is responsible for approximately 80% of clinical TPI deficiency.<sup id="cite_ref-Orphanet_18-1" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>TPI deficiency is very rare with less than 50 cases reported in literature.<sup id="cite_ref-TPI_paper_20-0" class="reference"><a href="#cite_note-TPI_paper-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Being an autosomal recessive inherited disease, TPI deficiency has a 25% recurrence risk in the case of heterozygous parents.<sup id="cite_ref-Orphanet_18-2" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TPI_paper_20-1" class="reference"><a href="#cite_note-TPI_paper-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> It is a congenital disease that most often occurs with hemolytic anemia and manifests with jaundice.<sup id="cite_ref-Orphanet_18-3" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Most patients with TPI for Glu104Asp mutation or heterozygous for a TPI null allele and Glu104Asp have a life expectancy of infancy to early childhood. TPI patients with other mutations generally show longer life expectancy. There are only two cases of individuals with TPI living beyond the age of 6. These cases involve two brothers from Hungary, one who did not develop neurological symptoms until the age of 12, and the older brother who has no neurological symptoms and suffers from anemia only.<sup id="cite_ref-Anemia_fact_21-0" class="reference"><a href="#cite_note-Anemia_fact-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Individuals with TPI show obvious symptoms after 6–24 months of age. These symptoms include: dystonia, tremor, dyskinesia, pyramidal tract signs, cardiomyopathy and spinal motor neuron involvement.<sup id="cite_ref-Orphanet_18-4" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Patients also show frequent respiratory system bacterial infections.<sup id="cite_ref-Orphanet_18-5" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>TPI is detected through deficiency of enzymatic activity and the build-up of dihyroxyacetone phosphate(DHAP), which is a toxic substrate, in erythrocytes.<sup id="cite_ref-Orphanet_18-6" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TPI_paper_20-2" class="reference"><a href="#cite_note-TPI_paper-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> This can be detected through physical examination and a series of lab work. In detection, there is generally myopathic changes seen in muscles and chronic axonal neuropathy found in the nerves.<sup id="cite_ref-Orphanet_18-7" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Diagnosis of TPI can be confirmed through molecular genetics.<sup id="cite_ref-Orphanet_18-8" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Chorionic villus DNA analysis or analysis of fetal red cells can be used to detect TPI in antenatal diagnosis.<sup id="cite_ref-Orphanet_18-9" class="reference"><a href="#cite_note-Orphanet-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><b>Treatment</b> for TPI is not specific, but varies according to different cases. Because of the range of symptoms TPI causes, a team of specialist may be needed to provide treatment to a single individual. That team of specialists would consists of pediatricians, cardiologists, neurologists, and other healthcare professionals, that can develop a comprehensive plan of action.<sup id="cite_ref-Treatment_of_TPI_22-0" class="reference"><a href="#cite_note-Treatment_of_TPI-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Supportive measures such as red cell transfusions in cases of severe anaemia can be taken to treat TPI as well. In some cases, spleen removal (splenectomy) may improve the anaemia. There is no treatment to prevent progressive neurological impairment of any other non-haematological clinical manifestation of the diseases.<sup id="cite_ref-enerca_23-0" class="reference"><a href="#cite_note-enerca-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_applications">Industrial applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=17" title="Edit section: Industrial applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>By far the most common use of isomerases in industrial applications is in <a href="/wiki/Sugar" title="Sugar">sugar</a> manufacturing. Glucose isomerase (also known as <a href="/wiki/Xylose_isomerase" title="Xylose isomerase">xylose isomerase</a>) catalyzes the conversion of D-<a href="/wiki/Xylose" title="Xylose">xylose</a> and D-<a href="/wiki/Glucose" title="Glucose">glucose</a> to D-<a href="/wiki/Xylulose" title="Xylulose">xylulose</a> and D-<a href="/wiki/Fructose" title="Fructose">fructose</a>. Like most sugar isomerases, glucose isomerase catalyzes the interconversion of <a href="/wiki/Aldose" title="Aldose">aldoses</a> and <a href="/wiki/Ketose" title="Ketose">ketoses</a>.<sup id="cite_ref-glucose_24-0" class="reference"><a href="#cite_note-glucose-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The conversion of glucose to fructose is a key component of <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">high-fructose corn syrup</a> production. <a href="/wiki/Isomerization" title="Isomerization">Isomerization</a> is more specific than older chemical methods of fructose production, resulting in a higher <a href="/wiki/Yield_(chemistry)" title="Yield (chemistry)">yield</a> of fructose and no <a href="/wiki/By-product" title="By-product">side products</a>.<sup id="cite_ref-glucose_24-1" class="reference"><a href="#cite_note-glucose-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The fructose produced from this isomerization reaction is purer with no residual flavors from <a href="/wiki/Contamination" title="Contamination">contaminants</a>. High-fructose corn syrup is preferred by many confectionery and soda manufacturers because of the high sweetening power of fructose (twice that of sucrose<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup>), its relatively low cost and its inability to crystallize. Fructose is also used as a sweetener for use by <a href="/wiki/Diabetics" class="mw-redirect" title="Diabetics">diabetics</a>.<sup id="cite_ref-glucose_24-2" class="reference"><a href="#cite_note-glucose-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Major issues of the use of glucose isomerase involve its inactivation at higher temperatures and the requirement for a high <a href="/wiki/PH" title="PH">pH</a> (between 7.0 and 9.0) in the reaction environment. Moderately high temperatures, above 70 °C, increase the yield of fructose by at least half in the isomerization step.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The enzyme requires a <a href="/wiki/Divalent" class="mw-redirect" title="Divalent">divalent</a> <a href="/wiki/Ion" title="Ion">cation</a> such as <a href="/wiki/Cobalt" title="Cobalt">Co<sup>2+</sup></a> and <a href="/wiki/Magnesium" title="Magnesium">Mg<sup>2+</sup></a> for peak activity, an additional cost to manufacturers. Glucose isomerase also has a much higher affinity for xylose than for glucose, necessitating a carefully controlled environment.<sup id="cite_ref-glucose_24-3" class="reference"><a href="#cite_note-glucose-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>The isomerization of xylose to xylulose has its own commercial applications as interest in <a href="/wiki/Biofuel" title="Biofuel">biofuels</a> has increased. This reaction is often seen naturally in <a href="/wiki/Detritivore" title="Detritivore">bacteria</a> that feed on decaying plant matter. Its most common industrial use is in the production of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, achieved by the <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> of <a href="/wiki/Xylulose" title="Xylulose">xylulose</a>. The use of <a href="/wiki/Hemicellulose" title="Hemicellulose">hemicellulose</a> as source material is very common. Hemicellulose contains <a href="/wiki/Xylan" title="Xylan">xylan</a>, which itself is composed of <a href="/wiki/Xylose" title="Xylose">xylose</a> in <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">β(1,4) linkages</a>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The use of glucose isomerase very efficiently converts xylose to xylulose, which can then be acted upon by fermenting <a href="/wiki/Yeast" title="Yeast">yeast</a>. Overall, extensive research in genetic engineering has been invested into optimizing glucose isomerase and facilitating its recovery from industrial applications for re-use. </p><p>Glucose isomerase is able to catalyze the isomerization of a range of other sugars, including D-<a href="/wiki/Ribose" title="Ribose">ribose</a>, D-<a href="/wiki/Allose" title="Allose">allose</a> and L-<a href="/wiki/Arabinose" title="Arabinose">arabinose</a>. The most efficient substrates are those similar to glucose and xylose, having <a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">equatorial</a> <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups at the third and fourth carbons.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The current model for the mechanism of glucose isomerase is that of a <a href="/wiki/Sigmatropic_reaction" title="Sigmatropic reaction">hydride shift</a> based on <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> and isotope exchange studies.<sup id="cite_ref-glucose_24-4" class="reference"><a href="#cite_note-glucose-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Membrane-associated_isomerases">Membrane-associated isomerases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isomerase&action=edit&section=18" title="Edit section: Membrane-associated isomerases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some isomerases associate with <a href="/wiki/Biological_membranes" class="mw-redirect" title="Biological membranes">biological membranes</a> as <a href="/wiki/Peripheral_membrane_protein" title="Peripheral membrane protein">peripheral membrane proteins</a> or anchored through a single <a href="/wiki/Transmembrane_helix" class="mw-redirect" title="Transmembrane helix">transmembrane helix</a>,<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> for example isomerases with the <a href="/wiki/Thioredoxin_domain" title="Thioredoxin domain">thioredoxin domain</a>, and certain <a href="/wiki/Prolyl_isomerase" title="Prolyl isomerase">prolyl isomerases</a>. </p> <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=Isomerase&action=edit&section=19" 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 reflist-columns references-column-width" style="column-width: 33em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</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 class="citation book cs1"><span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/enzymenomenclatu0000inte"><i>Enzyme nomenclature, 1978 recommendations of the Nomenclature Committee of the International Union of Biochemistry on the nomenclature and classification of enzymes</i></a></span>. New York: Academic Press. 1979. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780323144605" title="Special:BookSources/9780323144605"><bdi>9780323144605</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Enzyme+nomenclature%2C+1978+recommendations+of+the+Nomenclature+Committee+of+the+International+Union+of+Biochemistry+on+the+nomenclature+and+classification+of+enzymes.&rft.place=New+York&rft.pub=Academic+Press&rft.date=1979&rft.isbn=9780323144605&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fenzymenomenclatu0000inte&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-gold-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-gold_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-gold_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-gold_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcNaught1997" class="citation book cs1">McNaught AD (1997). <a rel="nofollow" class="external text" href="http://goldbook.iupac.org"><i>Compendium of Chemical Terminology</i></a> (2nd ed.). Oxford: Blackwell Scientific Publications. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9678550-9-7" title="Special:BookSources/978-0-9678550-9-7"><bdi>978-0-9678550-9-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Compendium+of+Chemical+Terminology&rft.place=Oxford&rft.edition=2nd&rft.pub=Blackwell+Scientific+Publications&rft.date=1997&rft.isbn=978-0-9678550-9-7&rft.aulast=McNaught&rft.aufirst=A.+D.&rft_id=http%3A%2F%2Fgoldbook.iupac.org&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-organic-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-organic_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWhitesellFox2004" class="citation book cs1">Whitesell JK, Fox MA (2004). <i>Organic Chemistry</i> (3rd ed.). Sudbury, Mass.: Jones and Bartlett. pp. 220–222. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7637-2197-8" title="Special:BookSources/978-0-7637-2197-8"><bdi>978-0-7637-2197-8</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=Sudbury%2C+Mass.&rft.pages=220-222&rft.edition=3rd&rft.pub=Jones+and+Bartlett&rft.date=2004&rft.isbn=978-0-7637-2197-8&rft.aulast=Whitesell&rft.aufirst=James+K.&rft.au=Fox%2C+Marye+Anne&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-kinetics-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-kinetics_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCornish-Bowden2013" class="citation book cs1"><a href="/wiki/Athel_Cornish-Bowden" title="Athel Cornish-Bowden">Cornish-Bowden A</a> (2013-02-22). <i>Fundamentals of Enzyme Kinetics</i> (4th ed.). 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Studies on rabbit muscle phosphoglucomutase with flux techniques"</a>. <i>The Biochemical Journal</i>. <b>110</b> (2): 161–80. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1042%2Fbj1100161">10.1042/bj1100161</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1187194">1187194</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5726186">5726186</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Biochemical+Journal&rft.atitle=The+mechanism+of+the+phosphoglucomutase+reaction.+Studies+on+rabbit+muscle+phosphoglucomutase+with+flux+techniques&rft.volume=110&rft.issue=2&rft.pages=161-80&rft.date=1968-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1187194%23id-name%3DPMC&rft_id=info%3Apmid%2F5726186&rft_id=info%3Adoi%2F10.1042%2Fbj1100161&rft.aulast=Britton&rft.aufirst=HG&rft.au=Clarke%2C+JB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1187194&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-essential-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-essential_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBruice2010" class="citation book cs1">Bruice PY (2010). <i>Essential Organic Chemistry</i> (2nd ed.). 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"Fermentation of a pentose by yeasts". <i>Biochemical and Biophysical Research Communications</i>. <b>94</b> (1): 248–54. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0006-291x%2880%2980213-0">10.1016/s0006-291x(80)80213-0</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6446306">6446306</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+and+Biophysical+Research+Communications&rft.atitle=Fermentation+of+a+pentose+by+yeasts&rft.volume=94&rft.issue=1&rft.pages=248-54&rft.date=1980-05&rft_id=info%3Adoi%2F10.1016%2Fs0006-291x%2880%2980213-0&rft_id=info%3Apmid%2F6446306&rft.aulast=Wang&rft.aufirst=PY&rft.au=Shopsis%2C+C&rft.au=Schneider%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChen1980" class="citation journal cs1">Chen WP (August–September 1980). "Glucose isomerase". <i>Process Biochemistry</i>. <b>15</b>: 36–41.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Process+Biochemistry&rft.atitle=Glucose+isomerase&rft.volume=15&rft.pages=36-41&rft.date=1980-08%2F1980-09&rft.aulast=Chen&rft.aufirst=WP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsomerase" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://membranome.org/protein_classes/13">Superfamilies of single-pass transmembrane lyases</a> in <a href="/wiki/Membranome_database" title="Membranome database">Membranome database</a></span> </li> </ol></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=Isomerase&action=edit&section=20" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090221090507/http://www.gopubmed.org/GoMeshPubMed/gomeshpubmed/?tool=HotTopicDirect&termAlt=mesh%237535">GoPubMed: Top authors, journals, places publishing on Isomerases</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol 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(biochemistry)">Cofactor</a></li> <li><a href="/wiki/Enzyme_catalysis" title="Enzyme catalysis">Enzyme catalysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Regulation</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/Allosteric_regulation" title="Allosteric regulation">Allosteric regulation</a></li> <li><a href="/wiki/Cooperativity" title="Cooperativity">Cooperativity</a></li> <li><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitor</a></li> <li><a href="/wiki/Enzyme_activator" title="Enzyme activator">Enzyme activator</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Classification</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/Enzyme_Commission_number" title="Enzyme Commission number">EC number</a></li> <li><a href="/wiki/Protein_superfamily" title="Protein superfamily">Enzyme superfamily</a></li> <li><a href="/wiki/Protein_family" title="Protein family">Enzyme family</a></li> <li><a href="/wiki/List_of_enzymes" title="List of enzymes">List of enzymes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kinetics</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/Enzyme_kinetics" title="Enzyme kinetics">Enzyme kinetics</a></li> <li><a href="/wiki/Eadie%E2%80%93Hofstee_diagram" title="Eadie–Hofstee diagram">Eadie–Hofstee diagram</a></li> <li><a href="/wiki/Hanes%E2%80%93Woolf_plot" title="Hanes–Woolf plot">Hanes–Woolf plot</a></li> <li><a href="/wiki/Lineweaver%E2%80%93Burk_plot" title="Lineweaver–Burk plot">Lineweaver–Burk plot</a></li> <li><a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">Michaelis–Menten kinetics</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</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><b>EC1 <a href="/wiki/Oxidoreductase" title="Oxidoreductase">Oxidoreductases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_1)" title="List of EC numbers (EC 1)">list</a>)</li> <li><b>EC2 <a href="/wiki/Transferase" title="Transferase">Transferases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_2)" title="List of EC numbers (EC 2)">list</a>)</li> <li><b>EC3 <a href="/wiki/Hydrolase" title="Hydrolase">Hydrolases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_3)" title="List of EC numbers (EC 3)">list</a>)</li> <li><b>EC4 <a href="/wiki/Lyase" title="Lyase">Lyases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_4)" title="List of EC numbers (EC 4)">list</a>)</li> <li><b>EC5 <a class="mw-selflink selflink">Isomerases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_5)" title="List of EC numbers (EC 5)">list</a>)</li> <li><b>EC6 <a href="/wiki/Ligase" title="Ligase">Ligases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_6)" title="List of EC numbers (EC 6)">list</a>)</li> <li><b>EC7 <a href="/wiki/Translocase" title="Translocase">Translocases</a></b> (<a href="/wiki/List_of_EC_numbers_(EC_7)" title="List of EC numbers (EC 7)">list</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 class="mw-selflink selflink">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 class="mw-selflink selflink">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 class="mw-selflink selflink">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 href="/wiki/Ketone" title="Ketone">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 class="mw-selflink selflink">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 class="mw-selflink selflink">Isomerase</a>: <a class="mw-selflink selflink">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 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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> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output 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