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id="toc-Vishal_Y_Joshi's_method" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vishal_Y_Joshi's_method"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Vishal Y Joshi's method</span> </div> </a> <ul id="toc-Vishal_Y_Joshi's_method-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Glycoside_hydrolases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glycoside_hydrolases"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Glycoside hydrolases</span> </div> </a> <ul id="toc-Glycoside_hydrolases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Glycosyltransferases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glycosyltransferases"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Glycosyltransferases</span> </div> </a> <ul id="toc-Glycosyltransferases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Disaccharide_phosphorylases" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Disaccharide_phosphorylases"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Disaccharide phosphorylases</span> </div> </a> <ul id="toc-Disaccharide_phosphorylases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Directed_glycosylations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Directed_glycosylations"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Directed glycosylations</span> </div> </a> <ul id="toc-Directed_glycosylations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-O-linked_glycopeptides;_pharmaceutical_uses_of_O-glycosylated_peptides" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#O-linked_glycopeptides;_pharmaceutical_uses_of_O-glycosylated_peptides"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>O-linked glycopeptides; pharmaceutical uses of O-glycosylated peptides</span> </div> </a> <ul id="toc-O-linked_glycopeptides;_pharmaceutical_uses_of_O-glycosylated_peptides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-N-Glycosidic_bonds_in_DNA" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#N-Glycosidic_bonds_in_DNA"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>N-Glycosidic bonds in DNA</span> </div> </a> <ul id="toc-N-Glycosidic_bonds_in_DNA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" 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class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Qlikozid_rabit%C9%99si" title="Qlikozid rabitəsi – Azerbaijani" lang="az" hreflang="az" data-title="Qlikozid rabitəsi" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Glikozidna_veza" title="Glikozidna veza – Bosnian" lang="bs" hreflang="bs" data-title="Glikozidna veza" 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/Enlla%C3%A7_glicos%C3%ADdic" title="Enllaç glicosídic – Catalan" lang="ca" hreflang="ca" data-title="Enllaç glicosídic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Glykosidov%C3%A1_vazba" title="Glykosidová vazba – Czech" lang="cs" hreflang="cs" data-title="Glykosidová vazba" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Glykosidbinding" title="Glykosidbinding – Danish" lang="da" hreflang="da" data-title="Glykosidbinding" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Glycosidische_Bindung" title="Glycosidische Bindung – German" lang="de" hreflang="de" data-title="Glycosidische Bindung" 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/Gl%C3%BCkosiidside" title="Glükosiidside – Estonian" lang="et" hreflang="et" data-title="Glükosiidside" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Enlace_glucos%C3%ADdico" title="Enlace glucosídico – Spanish" lang="es" hreflang="es" data-title="Enlace glucosídico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Lotura_glukosidiko" title="Lotura glukosidiko – Basque" lang="eu" hreflang="eu" data-title="Lotura glukosidiko" 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%BE%DB%8C%D9%88%D9%86%D8%AF_%DA%AF%D9%84%DB%8C%DA%A9%D9%88%D8%B2%DB%8C%D8%AF%DB%8C" title="پیوند گلیکوزیدی – Persian" lang="fa" hreflang="fa" data-title="پیوند گلیکوزیدی" 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/Liaison_osidique" title="Liaison osidique – French" lang="fr" hreflang="fr" data-title="Liaison osidique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Enlace_glicos%C3%ADdico" title="Enlace glicosídico – Galician" lang="gl" hreflang="gl" data-title="Enlace glicosídico" 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/%EA%B8%80%EB%A6%AC%EC%BD%94%EC%82%AC%EC%9D%B4%EB%93%9C_%EA%B2%B0%ED%95%A9" title="글리코사이드 결합 – Korean" lang="ko" hreflang="ko" data-title="글리코사이드 결합" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ikatan_glikosidik" title="Ikatan glikosidik – Indonesian" lang="id" hreflang="id" data-title="Ikatan glikosidik" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Legame_glicosidico" title="Legame glicosidico – Italian" lang="it" hreflang="it" data-title="Legame glicosidico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A9%D7%A8_%D7%92%D7%9C%D7%99%D7%A7%D7%95%D7%96%D7%99%D7%93%D7%99" title="קשר גליקוזידי – Hebrew" lang="he" hreflang="he" data-title="קשר גליקוזידי" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Ikatan_glikosidik" title="Ikatan glikosidik – Malay" lang="ms" hreflang="ms" data-title="Ikatan glikosidik" 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/Glycosidische_binding" title="Glycosidische binding – Dutch" lang="nl" hreflang="nl" data-title="Glycosidische binding" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B0%E3%83%AA%E3%82%B3%E3%82%B7%E3%83%89%E7%B5%90%E5%90%88" title="グリコシド結合 – Japanese" lang="ja" hreflang="ja" data-title="グリコシド結合" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Ligam_glicosidic" title="Ligam glicosidic – Occitan" lang="oc" hreflang="oc" data-title="Ligam glicosidic" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Wi%C4%85zanie_glikozydowe" title="Wiązanie glikozydowe – Polish" lang="pl" hreflang="pl" data-title="Wiązanie glikozydowe" 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/Liga%C3%A7%C3%A3o_glicos%C3%ADdica" title="Ligação glicosídica – Portuguese" lang="pt" hreflang="pt" data-title="Ligação glicosídica" 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/Leg%C4%83tur%C4%83_glicozidic%C4%83" title="Legătură glicozidică – Romanian" lang="ro" hreflang="ro" data-title="Legătură glicozidică" 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%93%D0%BB%D0%B8%D0%BA%D0%BE%D0%B7%D0%B8%D0%B4%D0%BD%D0%B0%D1%8F_%D1%81%D0%B2%D1%8F%D0%B7%D1%8C" title="Гликозидная связь – Russian" lang="ru" hreflang="ru" data-title="Гликозидная связь" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Glykozidov%C3%A1_v%C3%A4zba" title="Glykozidová väzba – Slovak" lang="sk" hreflang="sk" data-title="Glykozidová väzba" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Glikozidna_veza" title="Glikozidna veza – Serbian" lang="sr" hreflang="sr" data-title="Glikozidna veza" 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/Glikozidna_veza" title="Glikozidna veza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glikozidna veza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Glykosidisidos" title="Glykosidisidos – Finnish" lang="fi" hreflang="fi" data-title="Glykosidisidos" 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/Glykosidbindning" title="Glykosidbindning – Swedish" lang="sv" hreflang="sv" data-title="Glykosidbindning" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Glikosidik_ba%C4%9F" title="Glikosidik bağ – Turkish" lang="tr" hreflang="tr" data-title="Glikosidik bağ" 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%93%D0%BB%D1%96%D0%BA%D0%BE%D0%B7%D0%B8%D0%B4%D0%BD%D0%B8%D0%B9_%D0%B7%D0%B2%27%D1%8F%D0%B7%D0%BE%D0%BA" title="Глікозидний зв'язок – Ukrainian" lang="uk" hreflang="uk" 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Covalent bond joining a sugar molecule to another group</div> <p>A <b>glycosidic bond</b> or <b>glycosidic linkage</b> is a type of <a href="/wiki/Ether_bond" class="mw-redirect" title="Ether bond">ether bond</a> that joins a <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> (sugar) molecule to another group, which may or may not be another carbohydrate. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ethyl-glucoside.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ethyl-glucoside.png/550px-Ethyl-glucoside.png" decoding="async" width="550" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ethyl-glucoside.png/825px-Ethyl-glucoside.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ethyl-glucoside.png/1100px-Ethyl-glucoside.png 2x" data-file-width="1697" data-file-height="395" /></a><figcaption> Formation of ethyl glucoside: <a href="/wiki/Glucose" title="Glucose">Glucose</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> combine to form <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> <a href="/wiki/Glucoside" title="Glucoside">glucoside</a> and <a href="/wiki/Water" title="Water">water</a>. The reaction often favors formation of the α-glycosidic bond as shown due to the <a href="/wiki/Anomeric_effect" title="Anomeric effect">anomeric effect</a>.</figcaption></figure> <p>A glycosidic bond is formed between the <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> or <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a> group of a <a href="/wiki/Saccharide" class="mw-redirect" title="Saccharide">saccharide</a> (or a molecule derived from a saccharide) and the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> of some compound such as an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>. A substance containing a glycosidic bond is a <a href="/wiki/Glycoside" title="Glycoside">glycoside</a>. </p><p>The term 'glycoside' is now extended to also cover compounds with bonds formed between hemiacetal (or hemiketal) groups of sugars and several chemical groups other than hydroxyls, such as -SR (thioglycosides), -SeR (selenoglycosides), -NR<sup>1</sup>R<sup>2</sup> (N-glycosides), or even -CR<sup>1</sup>R<sup>2</sup>R<sup>3</sup> (C-glycosides). </p><p>Particularly in naturally occurring glycosides, the compound ROH from which the carbohydrate residue has been removed is often termed the aglycone, and the carbohydrate residue itself is sometimes referred to as the 'glycone'. </p> <div style="clear:both;" class=""></div> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="S-,_N-,_C-,_and_O-glycosidic_bonds"><span id="S-.2C_N-.2C_C-.2C_and_O-glycosidic_bonds"></span>S-, N-, C-, and O-glycosidic bonds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=1" title="Edit section: S-, N-, C-, and O-glycosidic bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Adenosin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Adenosin.svg/200px-Adenosin.svg.png" decoding="async" width="200" height="169" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Adenosin.svg/300px-Adenosin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Adenosin.svg/400px-Adenosin.svg.png 2x" data-file-width="200" data-file-height="169" /></a><figcaption><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a>, a component of <a href="/wiki/RNA" title="RNA">RNA</a>, results from the sugar <a href="/wiki/Ribose" title="Ribose">ribose</a> and <a href="/wiki/Adenine" title="Adenine">adenine</a> via the formation of an N-glycosidic bond (shown as the vertical line between the N and the sugar cycle)</figcaption></figure> <p>Glycosidic bonds of the form discussed above are known as <b>O-glycosidic bonds</b>, in reference to the glycosidic <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> that links the glycoside to the aglycone or reducing end sugar. In analogy, one also considers <b>S-glycosidic bonds</b> (which form <b>thioglycosides</b>), where the oxygen of the glycosidic bond is replaced with a <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> atom. In the same way, <b>N-glycosidic bonds</b>, have the glycosidic bond oxygen replaced with <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>. Substances containing N-glycosidic bonds are also known as <a href="/wiki/Glycosylamine" title="Glycosylamine">glycosylamines</a>. <b>C-glycosyl</b> bonds have the glycosidic oxygen replaced by a <a href="/wiki/Carbon" title="Carbon">carbon</a>; the term "C-glycoside" is considered a misnomer by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> and is discouraged.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> All of these modified glycosidic bonds have different susceptibility to hydrolysis, and in the case of C-glycosyl structures, they are typically more resistant to hydrolysis. </p> <div class="mw-heading mw-heading2"><h2 id="Numbering,_and_α/β_distinction_of_glycosidic_bonds"><span id="Numbering.2C_and_.CE.B1.2F.CE.B2_distinction_of_glycosidic_bonds"></span>Numbering, and α/β distinction of glycosidic bonds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=2" title="Edit section: Numbering, and α/β distinction of glycosidic bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Beta-1,6-linkage.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-1%2C6-linkage.svg/400px-Beta-1%2C6-linkage.svg.png" decoding="async" width="400" height="245" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-1%2C6-linkage.svg/600px-Beta-1%2C6-linkage.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-1%2C6-linkage.svg/800px-Beta-1%2C6-linkage.svg.png 2x" data-file-width="1095" data-file-height="670" /></a><figcaption>A β-1,6 <a href="/wiki/Beta-glucan" title="Beta-glucan">glucan</a> molecule showing how carbons are numbered. The terminal saccharide is linked via a β-1,6 glycosidic bond. The remaining linkages are all β-1,3.</figcaption></figure> <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">Main article: <a href="/wiki/Anomer" title="Anomer">Anomer</a></div> <p>When an anomeric center is involved in a glycosidic bond (as is common in nature) then one can distinguish between <b>α-</b> and <b>β-glycosidic bonds</b> by the relative stereochemistry of the anomeric position and the stereocenter furthest from C1 in the saccharide.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Pharmacologists often join substances to <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a> via glycosidic bonds in order to increase their water <a href="/wiki/Solubility" title="Solubility">solubility</a>; this is known as <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>. Many other <a href="/wiki/Glycoside" title="Glycoside">glycosides</a> have important physiological functions. </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_approaches">Chemical approaches</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=3" title="Edit section: Chemical approaches"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nüchter et al. (2001) have shown a new approach to <a href="/wiki/Fischer_glycosidation" title="Fischer glycosidation">Fischer glycosidation</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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><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> Employing a <a href="/wiki/Microwave" title="Microwave">microwave</a> oven equipped with <a href="/wiki/Reflux" title="Reflux">refluxing apparatus</a> in a rotor reactor with <a href="/wiki/Pressure_bomb" class="mw-redirect" title="Pressure bomb">pressure bombs</a>, Nüchter et al. (2001) were able to achieve 100% yield of α- and β-D-glucosides. This method can be performed on a multi-kilogram scale. </p> <div class="mw-heading mw-heading3"><h3 id="Vishal_Y_Joshi's_method"><span id="Vishal_Y_Joshi.27s_method"></span>Vishal Y Joshi's method</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=4" title="Edit section: Vishal Y Joshi's method"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> Joshi et al. (2006)<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> propose the <a href="/wiki/Koenigs-Knorr_reaction" class="mw-redirect" title="Koenigs-Knorr reaction">Koenigs-Knorr reaction</a> in the stereoselective synthesis of alkyl D-glucopyranosides via glycosylation, with the exception of using <a href="/wiki/Lithium_carbonate" title="Lithium carbonate">lithium carbonate</a> which is less expensive and toxic than the conventional method of using <a href="/wiki/Silver" title="Silver">silver</a> or <a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury</a> salts. D-glucose is first protected by forming the <a href="/wiki/Peracetate" class="mw-redirect" title="Peracetate">peracetate</a> by addition of <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, and then addition of <a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">hydrogen bromide</a> which brominates at the 5-position. On addition of the alcohol ROH and lithium carbonate, the OR replaces the bromine and on deprotecting the acetylated hydroxyls the product is synthesized in relatively high purity. It was suggested by Joshi et al. (2001) that lithium acts as the nucleophile that attacks the carbon at the 5-position and through a <a href="/wiki/Transition_state" title="Transition state">transition state</a> the alcohol is substituted for the bromine group. Advantages of this method as well as its stereoselectivity and low cost of the lithium salt include that it can be done at room temperature and its yield compares relatively well with the conventional Koenigs-Knorr method.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></p><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Vishal_Joshi.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Vishal_Joshi.png/220px-Vishal_Joshi.png" decoding="async" width="220" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Vishal_Joshi.png/330px-Vishal_Joshi.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Vishal_Joshi.png/440px-Vishal_Joshi.png 2x" data-file-width="647" data-file-height="342" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Glycoside_hydrolases">Glycoside hydrolases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=5" title="Edit section: Glycoside hydrolases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Glycoside_hydrolases" class="mw-redirect" title="Glycoside hydrolases">Glycoside hydrolases</a> (or glycosidases), are <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that break glycosidic bonds. Glycoside hydrolases typically can act either on α- or on β-glycosidic bonds, but not on both. This specificity allows researchers to obtain glycosides in high epimeric excess, one example being Wen-Ya Lu's conversion of D-Glucose to Ethyl β-D-glucopyranoside using naturally-derived glucosidase. Wen-Ya Lu utilized glucosidase in a reverse manner opposite to the enzyme's biological functionality:<sup id="cite_ref-:0_8-0" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png/545px-Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png" decoding="async" width="545" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png/818px-Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png/1090px-Glucosidase-catalyzed_glycosidation_of_D-Glucose_to_Ethyl_%CE%B2-D-glucopyranoside.png 2x" data-file-width="1992" data-file-height="708" /></a><figcaption>Lu, Wen-Ya et al. <i>Practical methods for Biocatalysis and Biotransformations</i>. <b>2010</b>, 236–239.<sup id="cite_ref-:0_8-1" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Glycosyltransferases">Glycosyltransferases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=6" title="Edit section: Glycosyltransferases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Before monosaccharide units are incorporated into glycoproteins, polysaccharides, or <a href="/wiki/Lipid" title="Lipid">lipids</a> in living organisms, they are typically first "activated" by being joined via a glycosidic bond to the <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> group of a <a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a> such as <a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">uridine diphosphate</a> (UDP), <a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">guanosine diphosphate</a> (GDP), <a href="/wiki/Thymidine_diphosphate" title="Thymidine diphosphate">thymidine diphosphate</a> (TDP), or <a href="/wiki/Cytidine_monophosphate" title="Cytidine monophosphate">cytidine monophosphate</a> (CMP). These activated biochemical intermediates are known as <a href="/wiki/Nucleotide_sugar" title="Nucleotide sugar">sugar nucleotides</a> or sugar donors. Many biosynthetic pathways use mono- or oligosaccharides activated by a diphosphate linkage to lipids, such as <a href="/wiki/Dolichol" title="Dolichol">dolichol</a>. These activated donors are then substrates for enzymes known as <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">glycosyltransferases</a>, which transfer the sugar unit from the activated donor to an accepting <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> (the acceptor substrate). </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Fluorine.Directed.Glycosylation.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Fluorine.Directed.Glycosylation.tif/lossless-page1-187px-Fluorine.Directed.Glycosylation.tif.png" decoding="async" width="187" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Fluorine.Directed.Glycosylation.tif/lossless-page1-281px-Fluorine.Directed.Glycosylation.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Fluorine.Directed.Glycosylation.tif/lossless-page1-374px-Fluorine.Directed.Glycosylation.tif.png 2x" data-file-width="6984" data-file-height="6418" /></a><figcaption><sup id="cite_ref-pmid20886497_9-0" class="reference"><a href="#cite_note-pmid20886497-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Disaccharide_phosphorylases">Disaccharide phosphorylases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=7" title="Edit section: Disaccharide phosphorylases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Different biocatalytic approaches have been developed toward the synthesis of glycosides in the past decades, which using "glycosyltransferases" and "glycoside hydrolases" are among the most common catalysis. The former often needs expensive materials and the later often shows low yields, De Winter et al.<sup id="cite_ref-De_WinterVan_Renterghem2015_10-0" class="reference"><a href="#cite_note-De_WinterVan_Renterghem2015-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> investigated use of <a href="/wiki/Cellobiose_phosphorylase" title="Cellobiose phosphorylase">cellobiose phosphorylase</a> (CP) toward synthesis of alpha-glycosides in ionic liquids. The best condition for use of CP was found to be in the presence of IL AMMOENG 101 and ethyl acetate. </p> <div class="mw-heading mw-heading2"><h2 id="Directed_glycosylations">Directed glycosylations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=8" title="Edit section: Directed glycosylations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Multiple chemical approaches exist to encourage selectivity of <b>α-</b> and <b>β-glycosidic bonds.</b> The highly substrate specific nature of the selectivity and the overall activity of the pyranoside can provide major synthetic difficulties. The overall specificity of the glycosylation can be improved by utilizing approaches which take into account the relative transition states that the anomeric carbon can undergo during a typical glycosylation. Most notably, recognition and incorporation of Felkin-Ahn-Eisenstein models into rationale chemical design can generally provide reliable results provided the transformation can undergo this type of conformational control in the transition state. </p><p>Fluorine directed glycosylations represent an encouraging handle for both B selectivity and introduction of a non-natural biomimetic C2 functionality on the carbohydrate. One innovative example provided by Bucher et al. provides a way to utilize a fluoro oxonium ion and the trichloroacetimidate to encourage B stereoselectivity through the gauche effect.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This reasonable stereoselectivity is clear through visualization of the Felkin-Ahn models of the possible chair forms. </p><p>This method represents an encouraging way to selectivity incorporate B-ethyl, isopropyl and other glycosides with typical trichloroacetimidate chemistry. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png/220px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png" decoding="async" width="220" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png/330px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png/440px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity_.png 2x" data-file-width="850" data-file-height="344" /></a><figcaption>Control of Oxonium ion – Felkin-Ahn stereoselectivity</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="O-linked_glycopeptides;_pharmaceutical_uses_of_O-glycosylated_peptides"><span id="O-linked_glycopeptides.3B_pharmaceutical_uses_of_O-glycosylated_peptides"></span>O-linked glycopeptides; pharmaceutical uses of O-glycosylated peptides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=9" title="Edit section: O-linked glycopeptides; pharmaceutical uses of O-glycosylated peptides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png/220px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png" decoding="async" width="220" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png/330px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png/440px-Control_of_Oxonium_ion_-_Felkin-Ahn_stereoselectivity2.png 2x" data-file-width="2516" data-file-height="772" /></a><figcaption>Control of oxonium ion – Felkin-Ahn stereoselectivity chair forms</figcaption></figure> <p>O-linked glycopeptides recently have been shown to exhibit excellent CNS permeability and efficacy in multiple animal models with disease states. In addition one of the most intriguing aspects thereof is the capability of O-glycosylation to extend half life, decrease clearance, and improve PK/PD thereof the active peptide beyond increasing CNS penetration. The innate utilization of sugars as solubilizing moieties in Phase II and III metabolism (glucuronic acids) has remarkably allowed an evolutionary advantage in that mammalian enzymes are not directly evolved to degrade O glycosylated products on larger moieties. </p><p>The peculiar nature of O-linked glycopeptides is that there are numerous examples which are CNS penetrant. The fundamental basis of this effect is thought to involve "membrane hopping" or "hop diffusion". The non-brownian motion driven "hop diffusion" process is thought to occur due to discontinuity of the plasma membrane. "Hop diffusion" notably combines free diffusion and intercomparmental transitions. Recent examples notably include high permeability of met-enkephalin analogs amongst other peptides. The full mOR agonist pentapeptide DAMGO is also CNS penetrant upon introduction of glycosylation.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="N-Glycosidic_bonds_in_DNA">N-Glycosidic bonds in DNA</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=10" title="Edit section: N-Glycosidic bonds in DNA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DNA molecules contain 5-membered carbon rings called riboses that are directly attached to two phosphate groups and a nucleobase that contains amino groups. The nitrogen atoms from the amino group in the nucleotides are covalently linked to the <a href="/wiki/Anomeric_effect" title="Anomeric effect">anomeric</a> carbon of the ribose sugar structure through an N-glycosidic bond. Occasionally, the nucleobases attached to the ribose undergo deamination, alkylation, or oxidation which results in cytotoxic lesions along the DNA backbone. These modifications severely threaten the cohesiveness of the DNA molecule, leading to the development of diseases such as cancer. <a href="/wiki/DNA_glycosylase" title="DNA glycosylase">DNA glycosylases</a> are enzymes that catalyze the hydrolysis the N-glycosidic bond to free the damaged or modified nucleobase from the DNA, by cleaving the carbon-nitrogen glycosidic bond at the 2' carbon, subsequently initiating the <a href="/wiki/Base_excision_repair" title="Base excision repair">base excision repair</a> (BER) pathway. </p><p>Monofunctional glycosylases catalyze the hydrolysis of the N-glycosidic bond via either a stepwise, S<sub>N</sub>1 like mechanism, or a concerted, S<sub>N</sub>2 like mechanism. The stepwise function, the nucleobase acts as a leaving group before the anomeric carbon gets attacked by the water molecule, producing a short-lived unstable <a href="/wiki/Oxocarbenium" title="Oxocarbenium">oxacarbenium</a> ion intermediate. This intermediate rapidly reacts with the nearby water molecule to substitute the N-glycosidic bond of the ribose and the nucleobase with an O-glycosidic bond with a hydroxy group. The concerted mechanism, the water acts as a nucleophile and attacks at the anomeric carbon before the nucelobase gets to act like a leaving group. The intermediate produced is a similar oxacarbenium ion where both the hydroxy groups and the nucleobase are still attached to the anomeric carbon. Both mechanisms theoretically yield the same product. Most ribonucleotides are hydrolyzed via the concerted S<sub>N</sub>2 like mechanism, while most deoxyribonucleotides proceed through the stepwise like mechanism. </p><p>These reactions are practically irreversible. Due to the fact that the cleavage of the N-glycosidic bond from the DNA backbone can lead to detrimental mutagenic and cytotoxic responses in an organism, have the ability to also catalyze the synthesis of N-glycosidic bonds by way of an abasic DNA site and a specific nucleobase.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosidic_bond&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.sbcs.qmul.ac.uk/iupac/2carb/33.html">"Nomenclature of Carbohydrates (Recommendations 1996)"</a>. <i>Department of Chemistry, Queen Mary University of London</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Department+of+Chemistry%2C+Queen+Mary+University+of+London&rft.atitle=Nomenclature+of+Carbohydrates+%28Recommendations+1996%29&rft_id=http%3A%2F%2Fwww.sbcs.qmul.ac.uk%2Fiupac%2F2carb%2F33.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosidic+bond" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBertozziRabuka2009" class="citation book cs1">Bertozzi C, Rabuka D (2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK1955/#_ch2_s4_">"Structural Basis of Glycan Diversity"</a>. 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Part 1. <b>16</b> (1): 65–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tetasy.2004.11.038">10.1016/j.tetasy.2004.11.038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron%3A+Asymmetry&rft.atitle=Biousian+glycopeptides+penetrate+the+blood%E2%80%93brain+barrier&rft.volume=16&rft.issue=1&rft.pages=65-75&rft.date=2005-01-10&rft_id=info%3Adoi%2F10.1016%2Fj.tetasy.2004.11.038&rft.aulast=Egleton&rft.aufirst=Richard+D.&rft.au=Bilsky%2C+Edward+J.&rft.au=Tollin%2C+Gordon&rft.au=Dhanasekaran%2C+Muthu&rft.au=Lowery%2C+John&rft.au=Alves%2C+Isabel&rft.au=Davis%2C+Peg&rft.au=Porreca%2C+Frank&rft.au=Yamamura%2C+Henry+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosidic+bond" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrohatMaiti2014" class="citation journal cs1">Drohat AC, Maiti A (November 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4238931">"Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA"</a>. <i>Organic & Biomolecular Chemistry</i>. <b>12</b> (42): 8367–8378. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc4ob01063a">10.1039/c4ob01063a</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4238931">4238931</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25181003">25181003</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+%26+Biomolecular+Chemistry&rft.atitle=Mechanisms+for+enzymatic+cleavage+of+the+N-glycosidic+bond+in+DNA&rft.volume=12&rft.issue=42&rft.pages=8367-8378&rft.date=2014-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4238931%23id-name%3DPMC&rft_id=info%3Apmid%2F25181003&rft_id=info%3Adoi%2F10.1039%2Fc4ob01063a&rft.aulast=Drohat&rft.aufirst=AC&rft.au=Maiti%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4238931&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosidic+bond" class="Z3988"></span></span> </li> </ol></div></div> <ul><li>Marco Brito-Arias, "Synthesis and Characterization of Glycosides", second edition, Editorial Springer 2016.</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=Glycosidic_bond&action=edit&section=12" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/G02661.html">Definition of glycosides</a>, from the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> Compendium of Chemical Terminology, the "<a href="/wiki/Gold_Book" class="mw-redirect" title="Gold Book">Gold Book</a>"</li> <li>Varki A et al. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=glyco.TOC&depth=10"><i>Essentials of Glycobiology.</i></a> Cold Spring Harbor Laboratory Press; 1999. 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class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink-fragment" href="#S-,_N-,_C-,_and_O-glycosidic_bonds">O-glycosidic bond</a></li> <li><a class="mw-selflink-fragment" href="#S-,_N-,_C-,_and_O-glycosidic_bonds">N-glycosidic bond</a></li> <li><a class="mw-selflink-fragment" href="#S-,_N-,_C-,_and_O-glycosidic_bonds">S-glycosidic bond</a></li> <li><a class="mw-selflink-fragment" href="#S-,_N-,_C-,_and_O-glycosidic_bonds">C-glycosidic bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isomer" title="Isomer">Geometry</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink-fragment" href="#Numbering,_and_α/β_distinction_of_glycosidic_bonds">α-Glycoside</a></li> <li><a class="mw-selflink-fragment" href="#Numbering,_and_α/β_distinction_of_glycosidic_bonds">β-Glycoside</a></li> <li><a class="mw-selflink-fragment" href="#Numbering,_and_α/β_distinction_of_glycosidic_bonds">1,4-Glycoside</a></li> <li><a class="mw-selflink-fragment" href="#Numbering,_and_α/β_distinction_of_glycosidic_bonds">1,6-Glycoside</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycoside" title="Glycoside">Glycone</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fructoside" title="Fructoside">Fructoside</a></li> <li><a href="/wiki/Galactoside" title="Galactoside">Galactoside</a></li> <li><a href="/wiki/Glucoside" title="Glucoside">Glucoside</a></li> <li><a href="/wiki/Glucuronide" title="Glucuronide">Glucuronide</a></li> <li><a href="/wiki/Rhamnoside" class="mw-redirect" title="Rhamnoside">Rhamnoside</a></li> <li><a href="/wiki/Riboside" title="Riboside">Riboside</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aglycone" title="Aglycone">Aglycone</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycoside#Alcoholic_glycosides" title="Glycoside">Alcoholic glycoside</a></li> <li><a href="/wiki/Cardiac_glycoside" title="Cardiac glycoside">Cardiac glycoside</a> <ul><li><a href="/wiki/Bufadienolide" title="Bufadienolide">Bufadienolide</a></li> <li><a href="/wiki/Cardenolide" title="Cardenolide">Cardenolide</a></li></ul></li> <li><a href="/wiki/Glycoside#Cyanogenic_glycosides" title="Glycoside">Cyanogenic glycoside</a></li> <li><a href="/wiki/Glycosylamine" title="Glycosylamine">Glycosylamine</a></li> <li><a href="/wiki/Glycoside#Phenolic_glycosides" title="Glycoside">Phenolic glycoside</a> <ul><li><a href="/wiki/Glycoside#Anthraquinone_glycosides" title="Glycoside">Anthraquinone glycoside</a></li> <li><a href="/wiki/Glycoside#Coumarin_glycosides" title="Glycoside">Coumarin glycoside</a></li> <li><a href="/wiki/Glycoside#Flavonoid_glycosides" title="Glycoside">Flavonoid glycoside</a></li></ul></li> <li><a href="/wiki/Saponin" title="Saponin">Saponin</a></li> <li><a href="/wiki/Steviol_glycoside" title="Steviol glycoside">Steviol glycoside</a></li> <li><a href="/wiki/Glycoside#Thioglycosides" title="Glycoside">Thioglycoside</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="Chemical_bonds" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" 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force">Intramolecular</a><br />(strong)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Covalent_bond" title="Covalent bond">Covalent</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/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metallic_bonding" title="Metallic bonding">Metallic</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/Metal_aromaticity" title="Metal aromaticity">Metal aromaticity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ionic_bonding" title="Ionic bonding">Ionic</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 class="mw-empty-elt"></li></ul> </div></td></tr></tbody></table><div></div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</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/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</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/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a href="/wiki/Halogen_bond" title="Halogen bond">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">Salt bridge</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/Bond_cleavage" title="Bond cleavage">Bond cleavage</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">Heterolysis</a></li> <li><a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">Homolysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_counting" title="Electron counting">Electron counting</a> rules</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</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 href="/wiki/Monosaccharide" title="Monosaccharide">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" 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