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nomenclature subsection</span> </button> <ul id="toc-Structure_and_nomenclature-sublist" class="vector-toc-list"> <li id="toc-Linear-chain_monosaccharides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Linear-chain_monosaccharides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Linear-chain monosaccharides</span> </div> </a> <ul id="toc-Linear-chain_monosaccharides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Open-chain_stereoisomers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Open-chain_stereoisomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Open-chain stereoisomers</span> </div> </a> <ul id="toc-Open-chain_stereoisomers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Configuration_of_monosaccharides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Configuration_of_monosaccharides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Configuration of monosaccharides</span> </div> </a> <ul id="toc-Configuration_of_monosaccharides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclisation_of_monosaccharides_(hemiacetal_formation)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyclisation_of_monosaccharides_(hemiacetal_formation)"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span><span><span>Cyclisation</span></span> of monosaccharides (hemiacetal formation)</span> </div> </a> <ul id="toc-Cyclisation_of_monosaccharides_(hemiacetal_formation)-sublist" class="vector-toc-list"> <li id="toc-Haworth_projection" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Haworth_projection"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4.1</span> <span>Haworth projection</span> </div> </a> <ul id="toc-Haworth_projection-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Derivatives</span> </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Literature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Literature"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Literature</span> </div> </a> <ul id="toc-Literature-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">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Monosaccharide</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 69 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-69" 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">69 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%B3%D9%83%D8%B1_%D8%A3%D8%AD%D8%A7%D8%AF%D9%8A" title="سكر أحادي – Arabic" lang="ar" hreflang="ar" data-title="سكر أحادي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Monosac%C3%A1ridu" title="Monosacáridu – Asturian" lang="ast" hreflang="ast" data-title="Monosacáridu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Monosaxarid" title="Monosaxarid – Azerbaijani" lang="az" hreflang="az" data-title="Monosaxarid" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%85%D9%88%D9%86%D9%88%D8%B3%D8%A7%DA%A9%D8%A7%D8%B1%DB%8C%D8%AF" title="مونوساکارید – South Azerbaijani" lang="azb" hreflang="azb" data-title="مونوساکارید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AE%E0%A6%A8%E0%A7%8B%E0%A6%B8%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%95%E0%A6%BE%E0%A6%B0%E0%A6%BE%E0%A6%87%E0%A6%A1" title="মনোস্যাকারাইড – Bangla" lang="bn" hreflang="bn" data-title="মনোস্যাকারাইড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Tan-thn%CC%82g" title="Tan-thn̂g – Minnan" lang="nan" hreflang="nan" data-title="Tan-thn̂g" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%B0%D1%86%D1%83%D0%BA%D1%80%D1%8B%D0%B4%D1%8B" title="Монацукрыды – Belarusian" lang="be" hreflang="be" data-title="Монацукрыды" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%B0%D1%86%D1%83%D0%BA%D1%80%D1%8B%D0%B4%D1%8B" title="Монацукрыды – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Монацукрыды" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%BE%D0%B7%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4" title="Монозахарид – Bulgarian" lang="bg" hreflang="bg" data-title="Монозахарид" 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/Monosaharidi" title="Monosaharidi – Bosnian" lang="bs" hreflang="bs" data-title="Monosaharidi" 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/Monosac%C3%A0rid" title="Monosacàrid – Catalan" lang="ca" hreflang="ca" data-title="Monosacàrid" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://cs.wikipedia.org/wiki/Monosacharidy" title="Monosacharidy – Czech" lang="cs" hreflang="cs" data-title="Monosacharidy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Monosaccharide" title="Monosaccharide – German" lang="de" hreflang="de" data-title="Monosaccharide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Monosahhariidid" title="Monosahhariidid – Estonian" lang="et" hreflang="et" data-title="Monosahhariidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9C%CE%BF%CE%BD%CE%BF%CF%83%CE%B1%CE%BA%CF%87%CE%B1%CF%81%CE%AF%CF%84%CE%B7%CF%82" title="Μονοσακχαρίτης – Greek" lang="el" hreflang="el" data-title="Μονοσακχαρίτης" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Monosac%C3%A1rido" title="Monosacárido – Spanish" lang="es" hreflang="es" data-title="Monosacárido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Monosa%C4%A5arido" title="Monosaĥarido – Esperanto" lang="eo" hreflang="eo" data-title="Monosaĥarido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Monosakarido" title="Monosakarido – Basque" lang="eu" hreflang="eu" data-title="Monosakarido" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D9%86%D9%88%D8%B3%D8%A7%DA%A9%D8%A7%D8%B1%DB%8C%D8%AF" title="منوساکارید – Persian" lang="fa" hreflang="fa" data-title="منوساکارید" 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/Ose" title="Ose – French" lang="fr" hreflang="fr" data-title="Ose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Monosacharide" title="Monosacharide – Western Frisian" lang="fy" hreflang="fy" data-title="Monosacharide" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Monaisi%C3%BAicr%C3%ADd" title="Monaisiúicríd – Irish" lang="ga" hreflang="ga" data-title="Monaisiúicríd" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Monosac%C3%A1rido" title="Monosacárido – Galician" lang="gl" hreflang="gl" data-title="Monosacárido" 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/%EB%8B%A8%EB%8B%B9%EB%A5%98" title="단당류 – Korean" lang="ko" hreflang="ko" data-title="단당류" 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/%D5%84%D5%B8%D5%B6%D5%B8%D5%BD%D5%A1%D5%AD%D5%A1%D6%80%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Մոնոսախարիդներ – Armenian" lang="hy" hreflang="hy" data-title="Մոնոսախարիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%95%E0%A4%B2%E0%A4%B6%E0%A4%B0%E0%A5%8D%E0%A4%95%E0%A4%B0%E0%A4%BE" title="एकलशर्करा – Hindi" lang="hi" hreflang="hi" data-title="एकलशर्करा" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Monosaharidi" title="Monosaharidi – Croatian" lang="hr" hreflang="hr" data-title="Monosaharidi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Ozo" title="Ozo – Ido" lang="io" hreflang="io" data-title="Ozo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Monosakarida" title="Monosakarida – Indonesian" lang="id" hreflang="id" data-title="Monosakarida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-zu mw-list-item"><a href="https://zu.wikipedia.org/wiki/IsiNcithinye" title="IsiNcithinye – Zulu" lang="zu" hreflang="zu" data-title="IsiNcithinye" data-language-autonym="IsiZulu" data-language-local-name="Zulu" class="interlanguage-link-target"><span>IsiZulu</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Einsykrur" title="Einsykrur – Icelandic" lang="is" hreflang="is" data-title="Einsykrur" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Monosaccaridi" title="Monosaccaridi – Italian" lang="it" hreflang="it" data-title="Monosaccaridi" 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%97%D7%93-%D7%A1%D7%95%D7%9B%D7%A8" title="חד-סוכר – Hebrew" lang="he" hreflang="he" data-title="חד-סוכר" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%BE%D1%81%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4%D1%82%D0%B5%D1%80" title="Моносахаридтер – Kazakh" lang="kk" hreflang="kk" data-title="Моносахаридтер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Monosakar%C3%AEd" title="Monosakarîd – Kurdish" lang="ku" hreflang="ku" data-title="Monosakarîd" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%BE%D1%81%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4%D0%B4%D0%B5%D1%80" title="Моносахариддер – Kyrgyz" lang="ky" hreflang="ky" data-title="Моносахариддер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Monosahar%C4%ABdi" title="Monosaharīdi – Latvian" lang="lv" hreflang="lv" data-title="Monosaharīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Monosacharidai" title="Monosacharidai – Lithuanian" lang="lt" hreflang="lt" data-title="Monosacharidai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Monoszacharid" title="Monoszacharid – Hungarian" lang="hu" hreflang="hu" data-title="Monoszacharid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D0%BE%D0%BD%D0%BE%D1%81%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4" title="Моносахарид – Macedonian" lang="mk" hreflang="mk" data-title="Моносахарид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Monosakarida" title="Monosakarida – Malay" lang="ms" hreflang="ms" data-title="Monosakarida" 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/Monosacharide" title="Monosacharide – Dutch" lang="nl" hreflang="nl" data-title="Monosacharide" 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/%E5%8D%98%E7%B3%96" title="単糖 – Japanese" lang="ja" hreflang="ja" data-title="単糖" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Enkle_sukkerarter" title="Enkle sukkerarter – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Enkle sukkerarter" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Monosakkarid" title="Monosakkarid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Monosakkarid" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/%C3%92sa" title="Òsa – Occitan" lang="oc" hreflang="oc" data-title="Òsa" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Monosaxaridlar" title="Monosaxaridlar – Uzbek" lang="uz" hreflang="uz" data-title="Monosaxaridlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Monosacharydy" title="Monosacharydy – Polish" lang="pl" hreflang="pl" data-title="Monosacharydy" 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/Monossacar%C3%ADdeo" title="Monossacarídeo – Portuguese" lang="pt" hreflang="pt" data-title="Monossacarídeo" 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/Monozaharid%C4%83" title="Monozaharidă – Romanian" lang="ro" hreflang="ro" data-title="Monozaharidă" 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%9C%D0%BE%D0%BD%D0%BE%D1%81%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4%D1%8B" title="Моносахариды – Russian" lang="ru" hreflang="ru" data-title="Моносахариды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Monosakaridet" title="Monosakaridet – Albanian" lang="sq" hreflang="sq" data-title="Monosakaridet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%B8%E0%B7%9C%E0%B6%B1%E0%B7%9C%E0%B7%83%E0%B7%90%E0%B6%9A%E0%B6%BB%E0%B6%BA%E0%B7%92%E0%B6%A9" title="මොනොසැකරයිඩ – Sinhala" lang="si" hreflang="si" data-title="මොනොසැකරයිඩ" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Monosaccharide" title="Monosaccharide – Simple English" lang="en-simple" hreflang="en-simple" data-title="Monosaccharide" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Monosacharid" title="Monosacharid – Slovak" lang="sk" hreflang="sk" data-title="Monosacharid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Monosaharid" title="Monosaharid – Slovenian" lang="sl" hreflang="sl" data-title="Monosaharid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Monosaharid" title="Monosaharid – Serbian" lang="sr" hreflang="sr" data-title="Monosaharid" 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/Monosaharidi" title="Monosaharidi – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Monosaharidi" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Monosakarida" title="Monosakarida – Sundanese" lang="su" hreflang="su" data-title="Monosakarida" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Monosakkaridi" title="Monosakkaridi – Finnish" lang="fi" hreflang="fi" data-title="Monosakkaridi" 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/Monosackarid" title="Monosackarid – Swedish" lang="sv" hreflang="sv" data-title="Monosackarid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%92%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AF%88%E0%AE%9A%E0%AF%8D%E0%AE%9A%E0%AE%B0%E0%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%B0%E0%AF%88" title="ஒற்றைச்சர்க்கரை – Tamil" lang="ta" hreflang="ta" data-title="ஒற்றைச்சர்க்கரை" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%82%E0%B8%A1%E0%B9%82%E0%B8%99%E0%B9%81%E0%B8%8B%E0%B9%87%E0%B8%81%E0%B8%84%E0%B8%B2%E0%B9%84%E0%B8%A3%E0%B8%94%E0%B9%8C" title="โมโนแซ็กคาไรด์ – Thai" lang="th" hreflang="th" data-title="โมโนแซ็กคาไรด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Monosakkarit" title="Monosakkarit – Turkish" lang="tr" hreflang="tr" data-title="Monosakkarit" 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%9C%D0%BE%D0%BD%D0%BE%D1%81%D0%B0%D1%85%D0%B0%D1%80%D0%B8%D0%B4%D0%B8" title="Моносахариди – Ukrainian" lang="uk" hreflang="uk" data-title="Моносахариди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Monosaccharide" title="Monosaccharide – Vietnamese" lang="vi" hreflang="vi" data-title="Monosaccharide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%8D%95%E7%B3%96" title="单糖 – Wu" lang="wuu" hreflang="wuu" data-title="单糖" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%96%AE%E9%86%A3" title="單醣 – Cantonese" lang="yue" hreflang="yue" data-title="單醣" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%96%AE%E9%86%A3" title="單醣 – Chinese" lang="zh" hreflang="zh" data-title="單醣" 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 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Chemically, monosaccharides are polyhydroxy aldehydes with the formula <span class="chemf nowrap">H-[CHOH]<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">n</sub></span></span>-CHO</span> or polyhydroxy ketones with the formula <span class="chemf nowrap">H-[CHOH]<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">m</sub></span></span>-CO-[CHOH]<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">n</sub></span></span>-H</span> with three or more carbon atoms.<sup id="cite_ref-:1_1-0" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>They are usually <a href="/wiki/Transparency_and_translucency" title="Transparency and translucency">colorless</a>, <a href="/wiki/Water" title="Water">water</a>-<a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a>, and <a href="/wiki/Crystal" title="Crystal">crystalline</a> organic solids. Contrary to their name (sugars), only some monosaccharides have a <a href="/wiki/Sweetness" title="Sweetness">sweet taste</a>. Most monosaccharides have the formula (CH<sub>2</sub>O)<sub><i>x</i></sub> (though not all molecules with this formula are monosaccharides). </p><p>Examples of monosaccharides include <a href="/wiki/Glucose" title="Glucose">glucose</a> (dextrose), <a href="/wiki/Fructose" title="Fructose">fructose</a> (levulose), and <a href="/wiki/Galactose" title="Galactose">galactose</a>. Monosaccharides are the building blocks of <a href="/wiki/Disaccharide" title="Disaccharide">disaccharides</a> (such as <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, <a href="/wiki/Lactose" title="Lactose">lactose</a> and <a href="/wiki/Maltose" title="Maltose">maltose</a>) and <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> (such as <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> and <a href="/wiki/Starch" title="Starch">starch</a>). The <a href="/wiki/White_sugar" title="White sugar">table sugar</a> used in everyday vernacular is itself a disaccharide sucrose comprising one molecule of each of the two monosaccharides <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-fructose.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Each <a href="/wiki/Carbon" title="Carbon">carbon</a> atom that supports a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>, except those at the end of the chain. This gives rise to a number of <a href="/wiki/Isomer" title="Isomer">isomeric</a> forms, all with the same chemical formula. For instance, galactose and glucose are both <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexoses</a>, but have different physical structures and chemical properties. </p><p>The monosaccharide glucose plays a pivotal role in <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, where the chemical energy is extracted through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> and the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> to provide energy to living organisms. Maltose is the <a href="/wiki/Condensation_reaction" title="Condensation reaction">dehydration condensate</a> of two glucose molecules. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_nomenclature">Structure and nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=1" title="Edit section: Structure and nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Monosaccharide_nomenclature" title="Monosaccharide nomenclature">Monosaccharide nomenclature</a></div> <p>With few exceptions (e.g., <a href="/wiki/Deoxyribose" title="Deoxyribose">deoxyribose</a>), monosaccharides have the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> (CH<sub>2</sub>O)<sub><i>x</i></sub>, where conventionally <i>x</i> ≥ 3.<sup id="cite_ref-:1_1-1" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Monosaccharides can be classified by the number <i>x</i> of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms they contain: <a href="/wiki/Triose" title="Triose">triose</a> (3), <a href="/wiki/Tetrose" title="Tetrose">tetrose</a> (4), <a href="/wiki/Pentose" title="Pentose">pentose</a> (5), <a href="/wiki/Hexose" title="Hexose">hexose</a> (6), <a href="/wiki/Heptose" title="Heptose">heptose</a> (7), and so on. </p><p>Glucose, used as an energy source and for the synthesis of starch, glycogen and cellulose, is a <a href="/wiki/Hexose" title="Hexose">hexose</a>. Ribose and deoxyribose (in <a href="/wiki/RNA" title="RNA">RNA</a> and <a href="/wiki/DNA" title="DNA">DNA</a>, respectively) are pentose sugars. Examples of heptoses include the <a href="/wiki/Ketose" title="Ketose">ketoses</a> <a href="/wiki/Mannoheptulose" title="Mannoheptulose">mannoheptulose</a> and <a href="/wiki/Sedoheptulose" title="Sedoheptulose">sedoheptulose</a>. Monosaccharides with eight or more carbons are rarely observed as they are quite unstable. In <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solutions</a> monosaccharides exist as rings if they have more than four carbons. </p> <div class="mw-heading mw-heading3"><h3 id="Linear-chain_monosaccharides">Linear-chain monosaccharides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=2" title="Edit section: Linear-chain monosaccharides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Simple monosaccharides have a linear and unbranched carbon skeleton with one <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> (C=O) <a href="/wiki/Functional_group" title="Functional group">functional group</a>, and one <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (OH) group on each of the remaining carbon <a href="/wiki/Atom" title="Atom">atoms</a>. Therefore, the molecular structure of a simple monosaccharide can be written as H(CHOH)<sub><i>n</i></sub>(C=O)(CHOH)<sub><i>m</i></sub>H, where <span class="nowrap"><i>n</i> + 1 + <i>m</i> = <i>x</i></span>; so that its elemental formula is C<sub><i>x</i></sub>H<sub>2<i>x</i></sub>O<sub><i>x</i></sub>. </p><p>By convention, the carbon atoms are numbered from 1 to <i>x</i> along the backbone, starting from the end that is closest to the C=O group. Monosaccharides are the simplest units of carbohydrates and the simplest form of sugar. </p><p>If the carbonyl is at position 1 (that is, <i>n</i> or <i>m</i> is zero), the molecule begins with a <a href="/wiki/Formyl" class="mw-redirect" title="Formyl">formyl</a> group H(C=O)− and is technically an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>. In that case, the compound is termed an <a href="/wiki/Aldose" title="Aldose">aldose</a>. Otherwise, the molecule has a <a href="/wiki/Ketone" title="Ketone">ketone</a> group, a carbonyl −(C=O)− between two carbons; then it is formally a ketone, and is termed a ketose. Ketoses of biological interest usually have the carbonyl at position 2. </p><p>The various classifications above can be combined, resulting in names such as "aldohexose" and "ketotriose". </p><p>A more general nomenclature for open-chain monosaccharides combines a Greek prefix to indicate the number of carbons (tri-, tetr-, pent-, hex-, etc.) with the suffixes "-ose" for aldoses and "-ulose" for ketoses.<sup id="cite_ref-auto_3-0" class="reference"><a href="#cite_note-auto-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In the latter case, if the carbonyl is not at position 2, its position is then indicated by a numeric infix. So, for example, H(C=O)(CHOH)<sub>4</sub>H is pentose, H(CHOH)(C=O)(CHOH)<sub>3</sub>H is pentulose, and H(CHOH)<sub>2</sub>(C=O)(CHOH)<sub>2</sub>H is pent-3-ulose. </p> <div class="mw-heading mw-heading3"><h3 id="Open-chain_stereoisomers">Open-chain stereoisomers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=3" title="Edit section: Open-chain stereoisomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Two monosaccharides with equivalent <a href="/wiki/Molecular_graph" title="Molecular graph">molecular graphs</a> (same chain length and same carbonyl position) may still be distinct <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a>, whose molecules differ in spatial orientation. This happens only if the molecule contains a <a href="/wiki/Stereogenic_center" class="mw-redirect" title="Stereogenic center">stereogenic center</a>, specifically a carbon atom that is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> (connected to four distinct molecular sub-structures). Those four bonds can have any of two configurations in space distinguished by their <a href="/wiki/Handedness" title="Handedness">handedness</a>. In a simple open-chain monosaccharide, every carbon is chiral except the first and the last atoms of the chain, and (in ketoses) the carbon with the keto group. </p><p>For example, the triketose H(CHOH)(C=O)(CHOH)H (glycerone, <a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">dihydroxyacetone</a>) has no stereogenic center, and therefore exists as a single stereoisomer. The other triose, the aldose H(C=O)(CHOH)<sub>2</sub>H (<a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">glyceraldehyde</a>), has one chiral carbon—the central one, number 2—which is bonded to groups −H, −OH, −C(OH)H<sub>2</sub>, and −(C=O)H. Therefore, it exists as two stereoisomers whose molecules are mirror images of each other (like a left and a right glove). Monosaccharides with four or more carbons may contain multiple chiral carbons, so they typically have more than two stereoisomers. The number of distinct stereoisomers with the same diagram is bounded by 2<sup><i>c</i></sup>, where <i>c</i> is the total number of chiral carbons. </p><p>The <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a> is a systematic way of drawing the <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formula</a> of an acyclic monosaccharide so that the handedness of each chiral carbon is well specified. Each stereoisomer of a simple open-chain monosaccharide can be identified by the positions (right or left) in the Fischer diagram of the chiral hydroxyls (the hydroxyls attached to the chiral carbons). </p><p>Most stereoisomers are themselves chiral (distinct from their mirror images). In the Fischer projection, two mirror-image isomers differ by having the positions of all chiral hydroxyls reversed right-to-left. Mirror-image isomers are chemically identical in non-chiral environments, but usually have very different biochemical properties and occurrences in nature. </p><p>While most stereoisomers can be arranged in pairs of mirror-image forms, there are some non-chiral stereoisomers that are identical to their mirror images, in spite of having chiral centers. This happens whenever the molecular graph is symmetrical, as in the 3-ketopentoses H(CHOH)<sub>2</sub>(CO)(CHOH)<sub>2</sub>H, and the two halves are mirror images of each other. In that case, mirroring is equivalent to a half-turn rotation. For this reason, there are only three distinct 3-ketopentose stereoisomers, even though the molecule has two chiral carbons. </p><p>Distinct stereoisomers that are not mirror-images of each other usually have different chemical properties, even in non-chiral environments. Therefore, each mirror pair and each non-chiral stereoisomer may be given a specific <a href="/wiki/Monosaccharide_nomenclature" title="Monosaccharide nomenclature">monosaccharide name</a>. For example, there are 16 distinct aldohexose stereoisomers, but the name "glucose" means a specific pair of mirror-image aldohexoses. In the Fischer projection, one of the two glucose isomers has the hydroxyl at left on C3, and at right on C4 and C5; while the other isomer has the reversed pattern. These specific monosaccharide names have conventional three-letter abbreviations, like "Glu" for glucose and "Thr" for <a href="/wiki/Threose" title="Threose">threose</a>. </p><p>Generally, a monosaccharide with <i>n</i> asymmetrical carbons has 2<sup><i>n</i></sup> stereoisomers. The number of open chain stereoisomers for an aldose monosaccharide is larger by one than that of a ketose monosaccharide of the same length. Every ketose will have 2<sup>(<i>n</i>−3)</sup> stereoisomers where <i>n</i> > 2 is the number of carbons. Every aldose will have 2<sup>(<i>n</i>−2)</sup> stereoisomers where <i>n</i> > 2 is the number of carbons. These are also referred to as epimers which have the different arrangement of −OH and −H groups at the asymmetric or chiral carbon atoms (this does not apply to those carbons having the carbonyl functional group). </p> <div class="mw-heading mw-heading3"><h3 id="Configuration_of_monosaccharides">Configuration of monosaccharides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=4" title="Edit section: Configuration of monosaccharides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like many chiral molecules, the two stereoisomers of glyceraldehyde will gradually rotate the <a href="/wiki/Optical_rotation" title="Optical rotation">polarization direction</a> of linearly <a href="/wiki/Polarized_light" class="mw-redirect" title="Polarized light">polarized light</a> as it passes through it, even in solution. The two stereoisomers are identified with the prefixes <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-, according to the sense of rotation: <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glyceraldehyde is <a href="/wiki/Dextrorotatory" class="mw-redirect" title="Dextrorotatory">dextrorotatory</a> (rotates the polarization axis clockwise), while <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-glyceraldehyde is <a href="/wiki/Levorotatory" class="mw-redirect" title="Levorotatory">levorotatory</a> (rotates it counterclockwise). </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:DL-Glucose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/DL-Glucose.svg/300px-DL-Glucose.svg.png" decoding="async" width="300" height="243" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/DL-Glucose.svg/450px-DL-Glucose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/DL-Glucose.svg/600px-DL-Glucose.svg.png 2x" data-file-width="361" data-file-height="293" /></a><figcaption><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-glucose</figcaption></figure> <p>The <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>- prefixes are also used with other monosaccharides, to distinguish two particular stereoisomers that are mirror-images of each other. For this purpose, one considers the chiral carbon that is furthest removed from the C=O group. Its four bonds must connect to −H, −OH, −CH<sub>2</sub>(OH), and the rest of the molecule. If the molecule can be rotated in space so that the directions of those four groups match those of the analog groups in <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glyceraldehyde's C2, then the isomer receives the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- prefix. Otherwise, it receives the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>- prefix. </p><p>In the Fischer projection, the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>- prefixes specifies the configuration at the carbon atom that is second from bottom: <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- if the hydroxyl is on the right side, and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>- if it is on the left side. </p><p>Note that the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>- and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>- prefixes do not indicate the direction of rotation of polarized light, which is a combined effect of the arrangement at all chiral centers. However, the two enantiomers will always rotate the light in opposite directions, by the same amount. See also <a href="/wiki/Absolute_configuration#By_relative_configuration:_D-_and_L-" title="Absolute configuration"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D/L</span></span> system</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Cyclisation_of_monosaccharides_(hemiacetal_formation)"><span id="Cyclisation_of_monosaccharides_.28hemiacetal_formation.29"></span><style data-mw-deduplicate="TemplateStyles:r1238216509">.mw-parser-output .vanchor>:target~.vanchor-text{background-color:#b1d2ff}@media screen{html.skin-theme-clientpref-night .mw-parser-output .vanchor>:target~.vanchor-text{background-color:#0f4dc9}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .vanchor>:target~.vanchor-text{background-color:#0f4dc9}}</style><span class="vanchor"><span id="Cyclisation"></span><span class="vanchor-text">Cyclisation</span></span> of monosaccharides (hemiacetal formation)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=5" title="Edit section: Cyclisation of monosaccharides (hemiacetal formation)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A monosaccharide often switches from the acyclic (open-chain) form to a <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> form, through a <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> reaction between the carbonyl group and one of the hydroxyl groups of the same molecule. The reaction creates a ring of carbon atoms closed by one bridging <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom. The resulting molecule has a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> or <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a> group, depending on whether the linear form was an aldose or a ketose. The reaction is easily reversed, yielding the original open-chain form. </p><p>In these cyclic forms, the ring usually has five or six atoms. These forms are called <a href="/wiki/Furanose" title="Furanose">furanoses</a> and <a href="/wiki/Pyranose" title="Pyranose">pyranoses</a>, respectively—by analogy with <a href="/wiki/Furan" title="Furan">furan</a> and <a href="/wiki/Pyran" title="Pyran">pyran</a>, the simplest compounds with the same carbon-oxygen ring (although they lack the double bonds of these two molecules). For example, the aldohexose <a href="/wiki/Glucose" title="Glucose">glucose</a> may form a hemiacetal linkage between the aldehyde group on carbon 1 and the hydroxyl on carbon 4, yielding a molecule with a 5-membered ring, called <a href="/wiki/Glucofuranose" class="mw-redirect" title="Glucofuranose">glucofuranose</a>. The same reaction can take place between carbons 1 and 5 to form a molecule with a <span class="nowrap">6-membered</span> ring, called <a href="/wiki/Glucopyranose" class="mw-redirect" title="Glucopyranose">glucopyranose</a>. Cyclic forms with a seven-atom ring (the same of <a href="/wiki/Oxepane" title="Oxepane">oxepane</a>), rarely encountered, are called <a href="/wiki/Heptose" title="Heptose">heptoses</a>. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Existence_in_solution.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Existence_in_solution.png/500px-Existence_in_solution.png" decoding="async" width="500" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Existence_in_solution.png/750px-Existence_in_solution.png 1.5x, //upload.wikimedia.org/wikipedia/commons/0/09/Existence_in_solution.png 2x" data-file-width="774" data-file-height="240" /></a><figcaption>Conversion between the furanose, acyclic, and pyranose forms of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose</figcaption></figure> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Structure_of_D-pentoses.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Structure_of_D-pentoses.png/500px-Structure_of_D-pentoses.png" decoding="async" width="500" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Structure_of_D-pentoses.png/750px-Structure_of_D-pentoses.png 1.5x, //upload.wikimedia.org/wikipedia/commons/8/85/Structure_of_D-pentoses.png 2x" data-file-width="924" data-file-height="112" /></a><figcaption>Pyranose forms of some pentose sugars</figcaption></figure> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Structure_of_D-hexoses.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Structure_of_D-hexoses.png/500px-Structure_of_D-hexoses.png" decoding="async" width="500" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Structure_of_D-hexoses.png/750px-Structure_of_D-hexoses.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/79/Structure_of_D-hexoses.png 2x" data-file-width="924" data-file-height="317" /></a><figcaption>Pyranose forms of some hexose sugars</figcaption></figure> <p>For many monosaccharides (including glucose), the cyclic forms predominate, in the solid state and in solutions, and therefore the same name commonly is used for the open- and closed-chain isomers. Thus, for example, the term "glucose" may signify glucofuranose, glucopyranose, the open-chain form, or a mixture of the three. </p><p>Cyclization creates a new <a href="/wiki/Stereogenic" class="mw-redirect" title="Stereogenic">stereogenic</a> center at the carbonyl-bearing carbon. The −OH group that replaces the carbonyl's oxygen may end up in two distinct positions relative to the ring's midplane. Thus each open-chain monosaccharide yields two cyclic isomers (<a href="/wiki/Anomer" title="Anomer">anomers</a>), denoted by the prefixes α- and β-. The molecule can change between these two forms by a process called <a href="/wiki/Mutarotation" title="Mutarotation">mutarotation</a>, that consists in a reversal of the ring-forming reaction followed by another ring formation.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Haworth_projection">Haworth projection</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=6" title="Edit section: Haworth projection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The stereochemical structure of a cyclic monosaccharide can be represented in a <a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a>. In this diagram, the α-isomer for the pyranose form of a <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-aldohexose has the −OH of the <a href="/wiki/Anomeric_carbon" class="mw-redirect" title="Anomeric carbon">anomeric carbon</a> below the plane of the carbon atoms, while the β-isomer has the −OH of the anomeric carbon above the plane. Pyranoses typically adopt a chair conformation, similar to that of <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>. In this conformation, the α-isomer has the −OH of the anomeric carbon in an axial position, whereas the β-isomer has the −OH of the anomeric carbon in equatorial position (considering <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-aldohexose sugars).<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucopyranose.svg" class="mw-file-description" title="α-D-Glucopyranose"><img alt="α-D-Glucopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/111px-Alpha-D-Glucopyranose.svg.png" decoding="async" width="111" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/166px-Alpha-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/222px-Alpha-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span></div> <div class="gallerytext">α-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Glucopyranose</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucopyranose.svg" class="mw-file-description" title="β-D-Glucopyranose"><img alt="β-D-Glucopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/111px-Beta-D-Glucopyranose.svg.png" decoding="async" width="111" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/166px-Beta-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/222px-Beta-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span></div> <div class="gallerytext">β-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Glucopyranose</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Derivatives">Derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=7" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A large number of biologically important modified monosaccharides exist: </p> <ul><li><a href="/wiki/Amino_sugar" title="Amino sugar">Amino sugars</a> such as: <ul><li><a href="/wiki/Galactosamine" title="Galactosamine">galactosamine</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">glucosamine</a></li> <li><a href="/wiki/Sialic_acid" title="Sialic acid">sialic acid</a></li> <li><a href="/wiki/N-Acetylglucosamine" title="N-Acetylglucosamine"><i>N</i>-acetylglucosamine</a></li></ul></li> <li>Sulfosugars such as: <ul><li><a href="/wiki/Sulfoquinovose" title="Sulfoquinovose">sulfoquinovose</a></li></ul></li> <li>Others such as: <ul><li><a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a></li> <li><a href="/wiki/Mannitol" title="Mannitol">mannitol</a></li> <li><a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Monosaccharide_nomenclature" title="Monosaccharide nomenclature">Monosaccharide nomenclature</a></li> <li><a href="/wiki/Reducing_sugar" title="Reducing sugar">Reducing sugar</a></li> <li><a href="/wiki/Sugar_acid" title="Sugar acid">Sugar acid</a></li> <li><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohol</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-:1-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFIUPAC_Chemical_Nomenclature_and_Structure_Representation_Division2013" class="citation book cs1">IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-102.1.2". In Favre, Henri A.; Powell, Warren H. (eds.). <a rel="nofollow" class="external text" href="https://pubs.rsc.org/en/Content/eBook/978-0-85404-182-4"><i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013</i></a>. <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>–<a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=P-102.1.2&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pub=IUPAC%E2%80%93RSC&rft.date=2013&rft.isbn=978-0-85404-182-4&rft.au=IUPAC+Chemical+Nomenclature+and+Structure+Representation+Division&rft_id=https%3A%2F%2Fpubs.rsc.org%2Fen%2FContent%2FeBook%2F978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMonosaccharide" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCollinsFerrier1995" class="citation book cs1">Collins, Peter M.; Ferrier, Robert J. (1995). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/30894482"><i>Monosaccharides : their chemistry and their roles in natural products</i></a>. Robert J. Ferrier. Chichester: Wiley & Sons. p. 4. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-95343-1" title="Special:BookSources/0-471-95343-1"><bdi>0-471-95343-1</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/30894482">30894482</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Monosaccharides+%3A+their+chemistry+and+their+roles+in+natural+products&rft.place=Chichester&rft.pages=4&rft.pub=Wiley+%26+Sons&rft.date=1995&rft_id=info%3Aoclcnum%2F30894482&rft.isbn=0-471-95343-1&rft.aulast=Collins&rft.aufirst=Peter+M.&rft.au=Ferrier%2C+Robert+J.&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F30894482&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMonosaccharide" class="Z3988"></span></span> </li> <li id="cite_note-auto-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-auto_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.rsc.org/Education/Teachers/Resources/cfb/Carbohydrates.htm">"Carbohydrates"</a>. <i>Chemistry for Biologists</i>. Royal Society of Chemistry<span class="reference-accessdate">. Retrieved <span class="nowrap">10 March</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+for+Biologists&rft.atitle=Carbohydrates&rft_id=http%3A%2F%2Fwww.rsc.org%2FEducation%2FTeachers%2FResources%2Fcfb%2FCarbohydrates.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMonosaccharide" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPigmanAnet,_E._F._L._J.1972" class="citation book cs1"><a href="/wiki/William_Ward_Pigman" title="William Ward Pigman">Pigman, William Ward</a>; Anet, E. F. L. J. (1972). "Chapter 4: Mutarotations and Actions of Acids and Bases". In Pigman and Horton (ed.). <i>The Carbohydrates: Chemistry and Biochemistry</i>. Vol. 1A (2nd ed.). San Diego: Academic Press. pp. 165–194.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+4%3A+Mutarotations+and+Actions+of+Acids+and+Bases&rft.btitle=The+Carbohydrates%3A+Chemistry+and+Biochemistry&rft.place=San+Diego&rft.pages=165-194&rft.edition=2nd&rft.pub=Academic+Press&rft.date=1972&rft.aulast=Pigman&rft.aufirst=William+Ward&rft.au=Anet%2C+E.+F.+L.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMonosaccharide" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/H02749.html">Haworth representation</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.H02749">10.1351/goldbook.H02749</a></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Literature">Literature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Monosaccharide&action=edit&section=10" title="Edit section: Literature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>McMurry, John. Organic Chemistry. 7th ed. Belmont, CA: Thomson Brooks/Cole, 2008. Print.</li></ul> <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=Monosaccharide&action=edit&section=11" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/monosaccharide" class="extiw" title="wiktionary:Special:Search/monosaccharide">monosaccharide</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20101013001727/http://www.chem.qmul.ac.uk/iupac/2carb/app.html">Nomenclature of Carbohydrates</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 dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist 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href="/wiki/List_of_sugars" title="List of sugars">List of sugars and sugar products</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chemistry</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Monosaccharide</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">Glucose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharide</a> <ul><li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li></ul></li> <li><a href="/wiki/Added_sugar" title="Added sugar">Added sugar</a></li> <li><a href="/wiki/Reducing_sugar" title="Reducing sugar">Reducing sugar</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sources</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sugar_beet" title="Sugar beet">Sugar beet</a></li> <li><a href="/wiki/Sugarcane" title="Sugarcane">Sugarcane</a></li> <li><a href="/wiki/Agave_syrup" title="Agave syrup">Agave syrup</a></li> <li><a href="/wiki/Birch_syrup" title="Birch syrup">Birch</a></li> <li><a href="/wiki/Coconut_sugar" title="Coconut sugar">Coconut</a></li> <li><a href="/wiki/Date_sugar" title="Date sugar">Date</a></li> <li><a href="/wiki/Honeydew_(secretion)" title="Honeydew (secretion)">Honeydew</a></li> <li><a href="/wiki/Maple_sugar" title="Maple sugar">Maple</a></li> <li><a href="/wiki/Palm_sugar" title="Palm sugar">Palm</a></li> <li><a href="/wiki/Malt_sugar" class="mw-redirect" title="Malt sugar">Malt</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Syrup" title="Syrup">Syrups</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_syrups" title="List of syrups">List of syrups</a></li> <li><a href="/wiki/Agave_syrup" title="Agave syrup">Agave syrup</a></li> <li><a href="/wiki/Barley_malt_syrup" title="Barley malt syrup">Barley malt syrup</a></li> <li><a href="/wiki/Brown_rice_syrup" title="Brown rice syrup">Brown rice syrup</a></li> <li><a href="/wiki/Cheong_(food)" title="Cheong (food)">Cheong</a> <ul><li><a href="/wiki/Maesil-cheong" class="mw-redirect" title="Maesil-cheong">Maesil-cheong</a></li> <li><a href="/wiki/Mogwa-cheong" class="mw-redirect" title="Mogwa-cheong">Mogwa-cheong</a></li> <li><a href="/wiki/Yuja-cheong" class="mw-redirect" title="Yuja-cheong">Yuja-cheong</a></li></ul></li> <li><a href="/wiki/Corn_syrup" title="Corn syrup">Corn syrup</a></li> <li><a href="/wiki/Glucose_syrup" title="Glucose syrup">Glucose syrup</a></li> <li><a href="/wiki/Golden_syrup" title="Golden syrup">Golden syrup</a></li> <li><a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a></li> <li><a href="/wiki/High-maltose_corn_syrup" title="High-maltose corn syrup">High-maltose corn syrup</a></li> <li><a href="/wiki/Honey" title="Honey">Honey</a></li> <li><a href="/wiki/Inverted_sugar_syrup" title="Inverted sugar syrup">Inverted sugar syrup</a></li> <li><a href="/wiki/Kuromitsu" title="Kuromitsu">Kuromitsu</a></li> <li><a href="/wiki/Maple_syrup" title="Maple syrup">Maple syrup</a></li> <li><a href="/wiki/Mizuame" title="Mizuame">Mizuame</a></li> <li><a href="/wiki/Molasses" title="Molasses">Molasses</a></li> <li><a href="/wiki/Pine_honey" title="Pine honey">Pine honey</a></li> <li><a href="/wiki/Steen%27s_cane_syrup" title="Steen's cane syrup">Steen's cane syrup</a></li> <li><a href="/wiki/Table_syrup" title="Table syrup">Table syrup</a></li> <li><a href="/wiki/Treacle" title="Treacle">Treacle</a></li> <li><a href="/wiki/Yac%C3%B3n_syrup" title="Yacón syrup">Yacón syrup</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Solid forms</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brown_sugar" title="Brown sugar">Brown</a> <ul><li><i><a href="/wiki/Peen_tong" title="Peen tong">Peen tong</a></i></li></ul></li> <li><a href="/wiki/Candi_sugar" title="Candi sugar">Candi sugar</a></li> <li><a href="/wiki/Chancaca" title="Chancaca">Chancaca</a></li> <li><a href="/wiki/Crystalline_fructose" class="mw-redirect" title="Crystalline fructose">Crystalline fructose</a></li> <li><a href="/wiki/Gelling_sugar" title="Gelling sugar">Gelling</a></li> <li><a href="/wiki/Gula_melaka" class="mw-redirect" title="Gula melaka">Gula melaka</a></li> <li><a href="/wiki/Jaggery" title="Jaggery">Jaggery</a></li> <li><a href="/wiki/Misri" class="mw-redirect" title="Misri">Misri</a></li> <li><a href="/wiki/Molasses_sugar" title="Molasses sugar">Molasses sugar</a></li> <li><a href="/wiki/Muscovado" title="Muscovado">Muscovado</a></li> <li><a href="/wiki/Nib_sugar" title="Nib sugar">Nib</a></li> <li><a href="/wiki/Non-centrifugal_cane_sugar" title="Non-centrifugal cane sugar">Non-centrifugal cane sugar</a></li> <li><a href="/wiki/Panela" title="Panela">Panela</a></li> <li><a href="/wiki/Plantation_Reserve" title="Plantation Reserve">Plantation Reserve</a></li> <li><a href="/wiki/Powdered_sugar" title="Powdered sugar">Powdered</a></li> <li><a href="/wiki/Preserving_sugar" title="Preserving sugar">Preserving</a></li> <li><a href="/wiki/Sucanat" title="Sucanat">Sucanat</a></li> <li><a href="/wiki/Sugar_candy" title="Sugar candy">Sugar candy</a> <ul><li><a href="/wiki/Barley_sugar" title="Barley sugar">Barley sugar</a></li> <li><a href="/wiki/Butterscotch" title="Butterscotch">Butterscotch</a></li> <li><a href="/wiki/Candy" title="Candy">Candy</a></li> <li><a href="/wiki/Hard_candy" title="Hard candy">Hard</a></li> <li><a href="/wiki/Rock_candy" title="Rock candy">Rock candy</a></li> <li><a href="/wiki/Toffee" title="Toffee">Toffee</a></li></ul></li> <li><a href="/wiki/Sugar_glass" title="Sugar glass">Sugar glass</a></li> <li><a href="/wiki/Sugarloaf" title="Sugarloaf">Sugarloaf</a></li> <li><a href="/wiki/Wasanbon" title="Wasanbon">Wasanbon</a></li> <li><a href="/wiki/White_sugar" title="White sugar">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other forms</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Caramel" title="Caramel">Caramel</a></li> <li><a href="/wiki/Cotton_candy" title="Cotton candy">Cotton candy floss</a></li> <li><a href="/wiki/List_of_foods_made_from_maple" title="List of foods made from maple">Maple sugar foods</a></li> <li><a href="/wiki/Rum" title="Rum">Rum</a></li> <li><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohol</a></li> <li><a href="/wiki/Confectionery#Sugar_confectionery" title="Confectionery">Sugar confectionery</a></li> <li><a href="/wiki/Sugarcane_juice" title="Sugarcane juice">Sugarcane juice</a></li> <li><a href="/wiki/Tuzem%C3%A1k" title="Tuzemák">Tuzemák</a></li> <li><a href="/wiki/List_of_unrefined_sweeteners" title="List of unrefined sweeteners">Unrefined sweeteners</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_industry" title="Sugar industry">Industry</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Production</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boilery" title="Boilery">Boilery</a></li> <li><a href="/wiki/Plantation#Sugar" title="Plantation">Plantation</a> <ul><li><a href="/wiki/Casa-grande" title="Casa-grande">Casa-grande</a></li></ul></li> <li><a href="/wiki/Sugar_refinery" title="Sugar refinery">Refinery</a></li> <li><a href="/wiki/Sugar_bush" title="Sugar bush">Sugar bush</a></li> <li><a href="/wiki/Sugarcane_mill" title="Sugarcane mill">Sugarcane mill</a></li> <li><a href="/wiki/Engenho" title="Engenho">Engenho</a></li> <li><a href="/wiki/Batey_(sugar_workers%27_town)" title="Batey (sugar workers' town)">Batey</a></li> <li><a href="/wiki/Zafra_(agriculture)" title="Zafra (agriculture)">Zafra</a></li> <li><a href="/wiki/Sugar_marketing" title="Sugar marketing">Sugar marketing</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By region (current)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_sugar_mills_in_Queensland" title="List of sugar mills in Queensland">Australia</a> <ul><li><a href="/wiki/Bundaberg_Sugar" title="Bundaberg Sugar">Bundaberg Sugar</a></li> <li><a href="/wiki/CSR_Limited" title="CSR Limited">CSR</a></li> <li><a href="/wiki/Wilmar_Sugar" class="mw-redirect" title="Wilmar Sugar">Wilmar Sugar</a></li></ul></li> <li><a href="/wiki/Cuban_sugar_economy" class="mw-redirect" title="Cuban sugar economy">Cuba</a></li> <li><a href="/wiki/Sugar_plantations_in_the_Caribbean" title="Sugar plantations in the Caribbean">Caribbean</a></li> <li><a href="/wiki/List_of_sugar_manufacturers_in_Kenya" title="List of sugar manufacturers in Kenya">Kenya</a></li> <li><a href="/wiki/Sugar_industry_of_India" title="Sugar industry of India">India</a></li> <li><a href="/wiki/Sugar_industry_of_Mauritius" title="Sugar industry of Mauritius">Mauritius</a></li> <li><a href="/wiki/Sugar_industry_of_the_Philippines" title="Sugar industry of the Philippines">Philippines</a></li> <li><a href="/wiki/Sugar_industry_of_Rwanda" title="Sugar industry of Rwanda">Rwanda</a></li> <li><a href="/wiki/Sugar_industry_of_Sri_Lanka" title="Sugar industry of Sri Lanka">Sri Lanka</a></li> <li><a href="/wiki/Agriculture_in_South_Africa#Sugarcane" title="Agriculture in South Africa">South Africa</a> <ul><li><a href="/wiki/Illovo_Sugar" title="Illovo Sugar">Illovo Sugar</a></li> <li><a href="/wiki/Tongaat_Hulett" title="Tongaat Hulett">Tongaat Hulett</a></li></ul></li> <li><a href="/wiki/List_of_sugar_manufacturers_in_Tanzania" title="List of sugar manufacturers in Tanzania">Tanzania</a></li> <li><a href="/wiki/Sugar_industry_of_Uganda" title="Sugar industry of Uganda">Uganda</a></li> <li>United Kingdom <ul><li><a href="/wiki/British_Sugar" title="British Sugar">British Sugar</a></li> <li><a href="/wiki/Tate_%26_Lyle" title="Tate & Lyle">Tate & Lyle</a></li></ul></li> <li><a href="/wiki/Sugar_industry_of_the_United_States" title="Sugar industry of the United States">United States</a> <ul><li><a href="/wiki/Sugar_Association" title="Sugar Association">Sugar Association</a></li> <li><a href="/wiki/U.S._Sugar_Program" title="U.S. Sugar Program">U.S. Sugar Program</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By region (historical)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sugar_production_in_the_Danish_West_Indies" title="Sugar production in the Danish West Indies">Danish West Indies</a></li> <li><a href="/wiki/Sugar_mills_in_Fiji" title="Sugar mills in Fiji">Fiji</a></li> <li><a href="/wiki/Sugar_plantations_in_Hawaii" title="Sugar plantations in Hawaii">Hawaii</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/History_of_sugar" title="History of sugar">History</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1811_German_Coast_uprising" title="1811 German Coast uprising">1811 German Coast uprising</a></li> <li><a href="/wiki/Amelioration_Act_1798" title="Amelioration Act 1798">Amelioration Act 1798</a></li> <li><a href="/wiki/Blackbirding" title="Blackbirding">Blackbirding</a></li> <li><a href="/wiki/Colonial_molasses_trade" title="Colonial molasses trade">Colonial molasses trade</a></li> <li><a href="/wiki/Demerara_rebellion_of_1823" title="Demerara rebellion of 1823">Demerara rebellion of 1823</a></li> <li><a href="/wiki/Holing_cane" title="Holing cane">Holing cane</a></li> <li><a href="/wiki/Leith_Sugar_House" title="Leith Sugar House">Leith Sugar House</a></li> <li><a href="/wiki/Molasses_Act" title="Molasses Act">Molasses Act</a></li> <li><a href="/wiki/Reciprocity_Treaty_of_1875" title="Reciprocity Treaty of 1875">Reciprocity Treaty of 1875</a></li> <li><a href="/wiki/Slavery_in_the_British_and_French_Caribbean" title="Slavery in the British and French Caribbean">Slavery in the British and French Caribbean</a></li> <li><a href="/wiki/Sugar_Act" title="Sugar Act">Sugar Act</a></li> <li><a href="/wiki/Sugar_Duties_Acts_1846" title="Sugar Duties Acts 1846">Sugar Duties Acts 1846</a></li> <li><a href="/wiki/Sugar_Intervention" title="Sugar Intervention">Sugar Intervention</a></li> <li><a href="/wiki/Taiwan_Sugar_Railways" title="Taiwan Sugar Railways">Taiwan Sugar Railways</a></li> <li><a href="/wiki/Triangular_trade" title="Triangular trade">Triangular trade</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Culture</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Added_sugar" title="Added sugar">Added sugar</a></li> <li><a href="/wiki/Crop_Over" title="Crop Over">Crop Over</a></li> <li><a href="/wiki/Sugar_shack" title="Sugar shack">Sugar shack</a></li> <li><a href="/wiki/Sugaring" title="Sugaring">Sugaring</a></li> <li><a href="/wiki/Sugar_nips" title="Sugar nips">Sugar nips</a></li> <li><a href="/wiki/Sugar_packet" title="Sugar packet">Sugar packet</a> <ul><li><a href="/wiki/Sucrology" class="mw-redirect" title="Sucrology">Sucrology</a></li></ul></li> <li><a href="/wiki/Sugar_people" title="Sugar people">Sugar people</a></li> <li><a href="/wiki/Sugar_tit" title="Sugar tit">Sugar tit</a></li> <li><a href="/wiki/Sugar_sculpture" title="Sugar sculpture">Sugar sculpture</a></li> <li><a href="/wiki/Treacle_mining" title="Treacle mining">Treacle mining</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Australian_Aboriginal_sweet_foods" class="mw-redirect" title="Australian Aboriginal sweet foods">Australian Aboriginal sweet foods</a></li> <li><a href="/wiki/Bagasse" title="Bagasse">Bagasse</a></li> <li><a href="/wiki/Blood_sugar_level" title="Blood sugar level">Blood sugar level</a></li> <li><a href="/wiki/Cane_knife" title="Cane knife">Cane knife</a></li> <li><a href="/wiki/Flavored_syrup" title="Flavored syrup">Flavored syrup</a></li> <li><a href="/wiki/Fruit_syrup" title="Fruit syrup">Fruit syrup</a> <ul><li><a href="/wiki/Date_honey" title="Date honey">Date honey</a></li> <li><a href="/wiki/Grape_syrup" title="Grape syrup">Grape</a></li> <li><a href="/wiki/Jallab" title="Jallab">Jallab</a></li></ul></li> <li><a href="/wiki/Health_effects_of_sugar" class="mw-redirect" title="Health effects of sugar">Health effects</a></li> <li><a href="/wiki/Nectar" title="Nectar">Nectar</a></li> <li><a href="/wiki/Sugar_addiction" class="mw-redirect" title="Sugar addiction">Sugar addiction</a></li> <li><a href="/wiki/Sugars_in_wine" title="Sugars in wine">Sugars in wine</a> <ul><li><a href="/wiki/Residual_sugar" class="mw-redirect" title="Residual sugar">Residual sugar</a></li></ul></li> <li><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sugar substitute</a></li> <li><a href="/wiki/Sweetened_beverage" title="Sweetened beverage">Sweetened beverage</a></li> <li><a href="/wiki/Sweetener" title="Sweetener">Sweetener</a></li> <li><a href="/wiki/Sweetness" title="Sweetness">Sweetness</a></li> <li><a href="/wiki/Vinasse" title="Vinasse">Vinasse</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Research</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Robert_Lustig" title="Robert Lustig">Robert Lustig</a></li> <li><a href="/wiki/John_Yudkin" title="John Yudkin">John Yudkin</a> <ul><li><i><a href="/wiki/Pure,_White_and_Deadly" title="Pure, White and Deadly">Pure, White and Deadly</a></i> (1972)</li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Sugar" title="Category:Sugar">Category</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Sugar_production" title="Category:Sugar production">Production</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="Types_of_carbohydrates" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Carbohydrates" title="Template:Carbohydrates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Carbohydrates" title="Template talk:Carbohydrates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Carbohydrates" title="Special:EditPage/Template:Carbohydrates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_carbohydrates" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldose" title="Aldose">Aldose</a></li> <li><a href="/wiki/Ketose" title="Ketose">Ketose</a></li> <li><a href="/wiki/Furanose" title="Furanose">Furanose</a></li> <li><a href="/wiki/Pyranose" title="Pyranose">Pyranose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geometry</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anomer" title="Anomer">Anomer</a></li> <li><a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">Cyclohexane conformation</a></li> <li><a href="/wiki/Epimer" title="Epimer">Epimer</a></li> <li><a href="/wiki/Mutarotation" title="Mutarotation">Mutarotation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Monosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diose" title="Diose">Dioses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldodiose <ul><li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triose" title="Triose">Trioses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotriose <ul><li><a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a></li></ul></li> <li>Ketotriose <ul><li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrose" title="Tetrose">Tetroses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotetroses <ul><li><a href="/wiki/Erythrose" title="Erythrose">Erythrose</a></li> <li><a href="/wiki/Threose" title="Threose">Threose</a></li></ul></li> <li>Ketotetrose <ul><li><a href="/wiki/Erythrulose" title="Erythrulose">Erythrulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pentose" title="Pentose">Pentoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldopentoses <ul><li><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a></li> <li><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li>Ketopentoses <ul><li><a href="/wiki/Ribulose" title="Ribulose">Ribulose</a></li> <li><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a></li></ul></li> <li><a href="/wiki/Deoxy_sugar" title="Deoxy sugar">Deoxy sugars</a> <ul><li><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">Aldohexoses</a> <ul><li><a href="/wiki/Allose" title="Allose">Allose</a></li> <li><a href="/wiki/Altrose" title="Altrose">Altrose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">Glucose</a></li> <li><a href="/wiki/Gulose" title="Gulose">Gulose</a></li> <li><a href="/wiki/Idose" title="Idose">Idose</a></li> <li><a href="/wiki/Mannose" title="Mannose">Mannose</a></li> <li><a href="/wiki/Talose" title="Talose">Talose</a></li></ul></li> <li><a href="/wiki/Ketohexose" class="mw-redirect" title="Ketohexose">Ketohexoses</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Psicose" title="Psicose">Psicose</a></li> <li><a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></li> <li><a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></li></ul></li> <li>Deoxy sugars <ul><li><a href="/wiki/Fucose" title="Fucose">Fucose</a></li> <li><a href="/wiki/Fuculose" title="Fuculose">Fuculose</a></li> <li><a href="/wiki/Rhamnose" title="Rhamnose">Rhamnose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heptose" title="Heptose">Heptoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ketoheptoses <ul><li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">Mannoheptulose</a></li> <li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">Sedoheptulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Above 7</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Octose" title="Octose">Octoses</a></li> <li><a href="/wiki/Nonose" title="Nonose">Nonoses</a> <ul><li><a href="/wiki/Neuraminic_acid" title="Neuraminic acid">Neuraminic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiple</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cellobiose" title="Cellobiose">Cellobiose</a></li> <li><a href="/wiki/Isomaltose" title="Isomaltose">Isomaltose</a></li> <li><a href="/wiki/Isomaltulose" title="Isomaltulose">Isomaltulose</a></li> <li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Lactulose" title="Lactulose">Lactulose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li> <li><a href="/wiki/Turanose" title="Turanose">Turanose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trisaccharide" title="Trisaccharide">Trisaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Maltotriose" title="Maltotriose">Maltotriose</a></li> <li><a href="/wiki/Melezitose" title="Melezitose">Melezitose</a></li> <li><a href="/wiki/Raffinose" title="Raffinose">Raffinose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrasaccharide" title="Tetrasaccharide">Tetrasaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stachyose" title="Stachyose">Stachyose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acarbose" title="Acarbose">Acarbose</a></li> <li><a href="/wiki/Fructooligosaccharide" title="Fructooligosaccharide">Fructooligosaccharide</a> (FOS)</li> <li><a href="/wiki/Galactooligosaccharide" title="Galactooligosaccharide">Galactooligosaccharide</a> (GOS)</li> <li><a href="/wiki/Isomaltooligosaccharide" title="Isomaltooligosaccharide">Isomaltooligosaccharide</a> (IMO)</li> <li><a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Oat_beta-glucan" title="Oat beta-glucan">Oat beta-glucan</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li> <li><a href="/wiki/Schizophyllan" title="Schizophyllan">Sizofiran</a></li> <li><a href="/wiki/Zymosan" title="Zymosan">Zymosan</a></li> <li><a href="/wiki/Cellulose" title="Cellulose">Cellulose</a></li> <li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li></ul></li> <li><a href="/wiki/Chitosan" title="Chitosan">Chitosan</a></li> <li><a href="/wiki/Dextrin" title="Dextrin">Dextrin</a> / <a href="/wiki/Dextran" title="Dextran">Dextran</a></li> <li><i><a href="/wiki/Fructose" title="Fructose">Fructose</a> / <a href="/wiki/Fructan" title="Fructan">Fructan</a></i> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulin</a></li></ul></li> <li><i><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactose" title="Galactose">Galactan</a></i></li> <li><i><a href="/wiki/Glucose" title="Glucose">Glucose</a> / <a href="/wiki/Glucan" title="Glucan">Glucan</a></i> <ul><li><a href="/wiki/Glycogen" title="Glycogen">Glycogen</a></li></ul></li> <li><a href="/wiki/Hemicellulose" title="Hemicellulose">Hemicellulose</a></li> <li><a href="/wiki/Levan_polysaccharide" title="Levan polysaccharide">Levan beta 2→6</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Mannans" title="Mannans">Mannan</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li> <li><a href="/wiki/Starch" title="Starch">Starch</a> <ul><li><a href="/wiki/Amylopectin" title="Amylopectin">Amylopectin</a></li> <li><a href="/wiki/Amylose" title="Amylose">Amylose</a></li></ul></li> <li><a href="/wiki/Xanthan_gum" title="Xanthan gum">Xanthan gum</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Carbohydrates" title="Category:Carbohydrates">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link 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