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id="toc-Abbreviations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Abbreviations"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Abbreviations</span> </div> </a> <ul id="toc-Abbreviations-sublist" class="vector-toc-list"> </ul> </li> </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">4</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">5</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">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">Glycosaminoglycan</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 30 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-30" 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">30 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%BA%D9%84%D9%8A%D9%83%D9%88%D8%B2_%D8%A3%D9%85%D9%8A%D9%86%D9%88%D8%BA%D9%84%D9%8A%D9%83%D8%A7%D9%86" title="غليكوز أمينوغليكان – Arabic" lang="ar" hreflang="ar" data-title="غليكوز أمينوغليكان" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Qlikozaminoqlikanlar" title="Qlikozaminoqlikanlar – Azerbaijani" lang="az" hreflang="az" data-title="Qlikozaminoqlikanlar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Glicosaminoglic%C3%A0" title="Glicosaminoglicà – Catalan" lang="ca" hreflang="ca" data-title="Glicosaminoglicà" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Glykosaminoglykane" title="Glykosaminoglykane – German" lang="de" hreflang="de" data-title="Glykosaminoglykane" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%93%CE%BB%CF%85%CE%BA%CE%BF%CE%B6%CE%B1%CE%BC%CE%B9%CE%BD%CE%BF%CE%B3%CE%BB%CF%85%CE%BA%CE%AC%CE%BD%CE%B5%CF%82" title="Γλυκοζαμινογλυκάνες – Greek" lang="el" hreflang="el" data-title="Γλυκοζαμινογλυκάνες" 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/Glicosoaminoglicano" title="Glicosoaminoglicano – Spanish" lang="es" hreflang="es" data-title="Glicosoaminoglicano" 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/Glikosaminglukano" title="Glikosaminglukano – Basque" lang="eu" hreflang="eu" data-title="Glikosaminglukano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D9%84%DB%8C%DA%A9%D9%88%D8%B2%D8%A2%D9%85%DB%8C%D9%86%D9%88%DA%AF%D9%84%DB%8C%DA%A9%D8%A7%D9%86" title="گلیکوزآمینوگلیکان – Persian" lang="fa" hreflang="fa" data-title="گلیکوزآمینوگلیکان" 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/Glycosaminoglycane" title="Glycosaminoglycane – French" lang="fr" hreflang="fr" data-title="Glycosaminoglycane" 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/Glicosaminoglicano" title="Glicosaminoglicano – Galician" lang="gl" hreflang="gl" data-title="Glicosaminoglicano" 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%EB%AF%B8%EB%85%B8%EA%B8%80%EB%A6%AC%EC%B9%B8" title="글리코사미노글리칸 – Korean" lang="ko" hreflang="ko" data-title="글리코사미노글리칸" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Glikozaminoglikan" title="Glikozaminoglikan – Croatian" lang="hr" hreflang="hr" data-title="Glikozaminoglikan" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Glikosaminoglikan" title="Glikosaminoglikan – Indonesian" lang="id" hreflang="id" data-title="Glikosaminoglikan" 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/Glicosamminoglicano" title="Glicosamminoglicano – Italian" lang="it" hreflang="it" data-title="Glicosamminoglicano" 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%92%D7%9C%D7%99%D7%A7%D7%95%D7%96%D7%90%D7%9E%D7%99%D7%A0%D7%95%D7%92%D7%9C%D7%99%D7%A7%D7%9F" title="גליקוזאמינוגליקן – Hebrew" lang="he" hreflang="he" data-title="גליקוזאמינוגליקן" 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/Glikosaminoglikan" title="Glikosaminoglikan – Malay" lang="ms" hreflang="ms" data-title="Glikosaminoglikan" 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/Glycosaminoglycaan" title="Glycosaminoglycaan – Dutch" lang="nl" hreflang="nl" data-title="Glycosaminoglycaan" 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%B5%E3%83%9F%E3%83%8E%E3%82%B0%E3%83%AA%E3%82%AB%E3%83%B3" title="グリコサミノグリカン – Japanese" lang="ja" hreflang="ja" data-title="グリコサミノグリカン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Glikozoaminoglikany" title="Glikozoaminoglikany – Polish" lang="pl" hreflang="pl" data-title="Glikozoaminoglikany" 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/Glicosaminoglicano" title="Glicosaminoglicano – Portuguese" lang="pt" hreflang="pt" data-title="Glicosaminoglicano" 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/Glicozaminoglican" title="Glicozaminoglican – Romanian" lang="ro" hreflang="ro" data-title="Glicozaminoglican" 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%B0%D0%BC%D0%B8%D0%BD%D0%BE%D0%B3%D0%BB%D0%B8%D0%BA%D0%B0%D0%BD%D1%8B" title="Гликозаминогликаны – Russian" lang="ru" hreflang="ru" data-title="Гликозаминогликаны" 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/Glykosaminoglyk%C3%A1n" title="Glykosaminoglykán – Slovak" lang="sk" hreflang="sk" data-title="Glykosaminoglykán" 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/Glikozaminoglikan" title="Glikozaminoglikan – Serbian" lang="sr" hreflang="sr" data-title="Glikozaminoglikan" 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/Glikozaminoglikan" title="Glikozaminoglikan – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glikozaminoglikan" 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/Glykosaminoglykaani" title="Glykosaminoglykaani – Finnish" lang="fi" hreflang="fi" data-title="Glykosaminoglykaani" 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/Glykosaminoglykan" title="Glykosaminoglykan – Swedish" lang="sv" hreflang="sv" data-title="Glykosaminoglykan" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%81%E0%B8%A5%E0%B9%82%E0%B8%84%E0%B8%AA%E0%B8%B0%E0%B8%A1%E0%B8%B4%E0%B9%82%E0%B8%99%E0%B9%84%E0%B8%81%E0%B8%A5%E0%B9%81%E0%B8%84%E0%B8%99" title="ไกลโคสะมิโนไกลแคน – Thai" lang="th" hreflang="th" data-title="ไกลโคสะมิโนไกลแคน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</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%B0%D0%BC%D1%96%D0%BD%D0%BE%D0%B3%D0%BB%D1%96%D0%BA%D0%B0%D0%BD%D0%B8" title="Глікозаміноглікани – Ukrainian" lang="uk" hreflang="uk" data-title="Глікозаміноглікани" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%B3%96%E8%83%BA%E8%81%9A%E7%B3%96" title="糖胺聚糖 – Chinese" lang="zh" hreflang="zh" data-title="糖胺聚糖" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q407553#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> 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searchaux" style="display:none">Polysaccharides found in animal tissue</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Technical plainlinks metadata ambox ambox-style ambox-technical" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>may be too technical for most readers to understand</b>.<span class="hide-when-compact"> Please <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Glycosaminoglycan&action=edit">help improve it</a> to <a href="/wiki/Wikipedia:Make_technical_articles_understandable" title="Wikipedia:Make technical articles understandable">make it understandable to non-experts</a>, without removing the technical details.</span> <span class="date-container"><i>(<span class="date">July 2015</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Chondroitin_Sulfate_Structure_NTP.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/240px-Chondroitin_Sulfate_Structure_NTP.png" decoding="async" width="240" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/360px-Chondroitin_Sulfate_Structure_NTP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/480px-Chondroitin_Sulfate_Structure_NTP.png 2x" data-file-width="977" data-file-height="422" /></a><figcaption>The repeating disaccharide unit (GlcUA(1β→3)GalNAc(1β→4))<sub>n</sub> of <a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">chondroitin sulfate</a>. For polysaccharide nomenclature see <a href="/wiki/Oligosaccharide_nomenclature" title="Oligosaccharide nomenclature">here</a>. R<sub>1</sub>, R<sub>2</sub>, R<sub>3</sub> may have different values.</figcaption></figure> <p><b>Glycosaminoglycans</b><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> (<b>GAGs</b>) or <b>mucopolysaccharides</b><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> are long, linear <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> consisting of repeating <a href="/wiki/Disaccharide" title="Disaccharide">disaccharide</a> units (i.e. two-sugar units). The repeating two-sugar unit consists of a <a href="/wiki/Uronic_acid" title="Uronic acid">uronic sugar</a> and an <a href="/wiki/Amino_sugar" title="Amino sugar">amino sugar</a>, except in the case of the <a href="/wiki/Sulfated" class="mw-redirect" title="Sulfated">sulfated</a> glycosaminoglycan <a href="/wiki/Keratan_sulfate" title="Keratan sulfate">keratan</a>, where, in place of the uronic sugar there is a <a href="/wiki/Galactose" title="Galactose">galactose</a> unit.<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> GAGs are found in vertebrates, invertebrates and bacteria.<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> Because GAGs are highly <a href="/wiki/Polar_molecule" class="mw-redirect" title="Polar molecule">polar molecules</a> and attract water; the body uses them as lubricants or shock absorbers. </p><p><a href="/wiki/Mucopolysaccharidosis" title="Mucopolysaccharidosis">Mucopolysaccharidoses</a> are a group of <a href="/wiki/Metabolic_disorder" title="Metabolic disorder">metabolic disorders</a> in which abnormal accumulations of glycosaminoglycans occur due to enzyme deficiencies. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glycosaminoglycans vary greatly in molecular mass, disaccharide structure, and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>. This is because GAG synthesis is not template driven, as are proteins or nucleic acids, but constantly altered by processing enzymes.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>GAGs are classified into four groups, based on their core disaccharide structures:<sup id="cite_ref-Sasisekharan_6-0" class="reference"><a href="#cite_note-Sasisekharan-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ol><li><a href="/wiki/Heparin" title="Heparin">Heparin</a>/heparan sulfate (HSGAGs)</li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a>/<a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">dermatan sulfate</a> (CSGAGs) which along with HSGAGs are synthesized in the <a href="/wiki/Golgi_apparatus" title="Golgi apparatus">Golgi apparatus</a>, where <a href="/wiki/Core_protein" class="mw-redirect" title="Core protein">protein cores</a>, made in the <a href="/wiki/Rough_endoplasmic_reticulum" class="mw-redirect" title="Rough endoplasmic reticulum">rough endoplasmic reticulum</a>, are post-translationally modified via <a href="/wiki/O-linked_glycosylation" title="O-linked glycosylation">O-linked glycosylation</a> by <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">glycosyltransferases</a>, thus forming <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycans</a>.</li> <li><a href="/wiki/Keratan_sulfate" title="Keratan sulfate">Keratan sulfate</a> which may modify core proteins through <a href="/wiki/N-linked_glycosylation" title="N-linked glycosylation">N-linked glycosylation</a> or O-linked glycosylation of the proteoglycan</li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a> (also known as hyaluronan), which is synthesized by integral membrane synthases, which immediately secrete the dynamically elongated disaccharide chain.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (July 2022)">clarification needed</span></a></i>]</sup></li></ol> <div class="mw-heading mw-heading3"><h3 id="HSGAG_and_CSGAG">HSGAG and CSGAG</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=2" title="Edit section: HSGAG and CSGAG"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>HSGAG and CSGAG modified proteoglycans first begin with a consensus Ser-Gly/Ala-X-Gly motif in the core protein. Construction of a tetrasaccharide linker that consists of -GlcAβ1–3Galβ1–3Galβ1–4Xylβ1-O-(Ser)-, where <a href="/wiki/Xylosyltransferase" title="Xylosyltransferase">xylosyltransferase</a>, β4-galactosyl transferase (GalTI),β3-galactosyl transferase (GalT-II), and β3-GlcA transferase (GlcAT-I) transfer the four monosaccharides, begins synthesis of the GAG modified protein. The first modification of the tetrasaccharide linker determines whether the HSGAGs or CSGAGs will be added. Addition of a GlcNAc promotes the addition of HSGAGs while addition of GalNAc to the tetrasaccharide linker promotes CSGAG development.<sup id="cite_ref-Sasisekharan_6-1" class="reference"><a href="#cite_note-Sasisekharan-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> GlcNAcT-I transfers GlcNAc to the tetrasaccahride linker, which is distinct from glycosyltransferase GlcNAcT-II, the enzyme that is utilized to build HSGAGs. EXTL2 and EXTL3, two genes in the EXT tumor suppressor family, have been shown to have GlcNAcT-I activity. Conversely, GalNAc is transferred to the linker by the enzyme GalNAcT to initiate synthesis of CSGAGs, an enzyme which may or may not have distinct activity compared to the GalNAc transferase activity of chondroitin synthase.<sup id="cite_ref-Sasisekharan_6-2" class="reference"><a href="#cite_note-Sasisekharan-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>With regard to HSGAGs, a multimeric enzyme encoded by EXT1 and EXT2 of the EXT family of genes, transfers both GlcNAc and GlcA for HSGAG chain elongation. While elongating, the HSGAG is dynamically modified, first by N-deacetylase, N-sulfotransferase (<a href="/wiki/NDST1" title="NDST1">NDST1</a>), which is a bifunctional enzyme that cleaves the N-acetyl group from GlcNAc and subsequently sulfates the N-position. Next, C-5 uronyl epimerase coverts d-GlcA to l-IdoA followed by 2-<i>O</i> sulfation of the uronic acid sugar by 2-<i>O</i> sulfotransferase (<a href="/wiki/Heparan_sulfate_2-O-sulfotransferase" title="Heparan sulfate 2-O-sulfotransferase">Heparan sulfate 2-O-sulfotransferase</a>). Finally, the 6-<i>O</i> and 3-<i>O</i> positions of GlcNAc moities are sulfated by 6-<i>O</i> (<a href="/wiki/Heparan_sulfate_6-O-sulfotransferase" title="Heparan sulfate 6-O-sulfotransferase">Heparan sulfate 6-O-sulfotransferase</a>) and 3-O (3-OST) sulfotransferases. </p><p>Chondroitin sulfate and dermatan sulfate, which comprise CSGAGs, are differentiated from each other by the presence of GlcA and IdoA epimers respectively. Similar to the production of HSGAGs, C-5 uronyl epimerase converts d-GlcA to l-IdoA to synthesize dermatan sulfate. Three sulfation events of the CSGAG chains occur: 4-<i>O</i> and/or 6-<i>O</i> sulfation of GalNAc and 2-<i>O</i> sulfation of uronic acid. Four isoforms of the 4-<i>O</i> GalNAc sulfotransferases (C4ST-1, C4ST-2, C4ST-3, and D4ST-1) and three isoforms of the GalNAc 6-<i>O</i> sulfotransferases (C6ST, C6ST-2, and GalNAc4S-6ST) are responsible for the sulfation of GalNAc.<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> <div class="mw-heading mw-heading3"><h3 id="Keratan_sulfate_types">Keratan sulfate types</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=3" title="Edit section: Keratan sulfate types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unlike HSGAGs and CSGAGs, the third class of GAGs, those belonging to <a href="/wiki/Keratan_sulfate" title="Keratan sulfate">keratan sulfate</a> types, are driven towards biosynthesis through particular protein sequence motifs. For example, in the cornea and cartilage, the keratan sulfate domain of <a href="/wiki/Aggrecan" title="Aggrecan">aggrecan</a> consists of a series of tandemly repeated hexapeptides with a consensus sequence of E(E/L)PFPS.<sup id="cite_ref-Funderburg_KS_synthesis_8-0" class="reference"><a href="#cite_note-Funderburg_KS_synthesis-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Additionally, for three other keratan sulfated proteoglycans, <a href="/wiki/Lumican" title="Lumican">lumican</a>, <a href="/wiki/Keratocan" title="Keratocan">keratocan</a>, and mimecan (<a href="/wiki/OGN_(gene)" class="mw-redirect" title="OGN (gene)">OGN</a>), the consensus sequence NX(T/S) along with protein secondary structure was determined to be involved in <i>N</i>-linked oligosaccharide extension with keratan sulfate.<sup id="cite_ref-Funderburg_KS_synthesis_8-1" class="reference"><a href="#cite_note-Funderburg_KS_synthesis-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Keratan sulfate elongation begins at the nonreducing ends of three linkage oligosaccharides, which define the three classes of keratan sulfate. Keratan sulfate I (KSI) is <i>N</i> -linked via a high mannose type precursor oligosaccharide. Keratan sulfate II (KSII) and keratan sulfate III (KSIII) are <i>O</i>-linked, with KSII linkages identical to that of <a href="/wiki/Mucin" title="Mucin">mucin</a> core structure, and KSIII linked to a 2-<i>O</i> mannose. Elongation of the keratan sulfate polymer occurs through the glycosyltransferase addition of Gal and GlcNAc. Galactose addition occurs primarily through the β-1,4-galactosyltransferase <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> (β4Gal-T1) while the enzymes responsible for β-3-Nacetylglucosamine have not been clearly identified. Finally, sulfation of the polymer occurs at the 6-position of both sugar residues. The enzyme KS-Gal6ST (<a href="/wiki/CHST1" title="CHST1">CHST1</a>) transfers sulfate groups to galactose while N-acetylglucosaminyl-6-sulfotransferase (GlcNAc6ST) (<a href="/wiki/CHST2" title="CHST2">CHST2</a>) transfers sulfate groups to terminal GlcNAc in keratan sulfate.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hyaluronic_acid_class">Hyaluronic acid class</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=4" title="Edit section: Hyaluronic acid class"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Hyaluronan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Hyaluronan.svg/240px-Hyaluronan.svg.png" decoding="async" width="240" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Hyaluronan.svg/360px-Hyaluronan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Hyaluronan.svg/480px-Hyaluronan.svg.png 2x" data-file-width="512" data-file-height="262" /></a><figcaption><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronan</a> (-4GlcUA<i>β</i>1-3GlcNAc<i>β</i>1-)<sub>n</sub></figcaption></figure> <p>The fourth class of GAG, <a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">hyaluronic acid</a> (HA), is not sulfated and is synthesized by three transmembrane synthase proteins <a href="/wiki/HAS1" title="HAS1">HAS1</a>, <a href="/wiki/HAS2" title="HAS2">HAS2</a>, and <a href="/wiki/HAS3" title="HAS3">HAS3</a>. HA, a linear polysaccharide, is composed of repeating disaccharide units of →4)GlcAβ(1→3)GlcNAcβ(1→ and has a very high molecular mass, <a href="/wiki/Ranging" class="mw-redirect" title="Ranging">ranging</a> from 10<sup>5</sup> to 10<sup>7</sup> Da. Each HAS enzyme is capable of transglycosylation when supplied with UDP-GlcA and UDP-GlcNAc.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><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> HAS2 is responsible for very large hyaluronic acid polymers, while smaller sizes of HA are synthesized by HAS1 and HAS3. While each HAS isoform catalyzes the same biosynthetic reaction, each HAS isoform is independently active. HAS isoforms have also been shown to have differing <i>K</i><sub>m</sub> values for UDP-GlcA and UDPGlcNAc.<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> It is believed that through differences in enzyme activity and expression, the wide spectrum of biological functions mediated by HA can be regulated, such as its involvement with <a href="/wiki/Neural_stem_cell" title="Neural stem cell">neural stem cell</a> regulation in the <a href="/wiki/Subgranular_zone" title="Subgranular zone">subgranular zone</a> of the brain. </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacodynamics">Pharmacodynamics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=5" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dt>HSGAGs</dt> <dd>Endogenous heparin is localized and stored in secretory granules of <a href="/wiki/Mast_cell" title="Mast cell">mast cells</a>. <a href="/wiki/Histamine" title="Histamine">Histamine</a> that is present within the granules is protonated (H<sub>2</sub>A<sup>2+</sup>) at pH within granules (5.2–6.0), thus it is believed that heparin, which is highly negatively charged, functions to electrostatically retain and store histamine.<sup id="cite_ref-Rabenstein_13-0" class="reference"><a href="#cite_note-Rabenstein-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In the clinic, heparin is administered as an anticoagulant and is also the first line choice for thromboembolic diseases.<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><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> Heparan sulfate (HS) has numerous biological activities and functions, including cell adhesion, regulation of cell growth and proliferation, developmental processes, cell surface binding of lipoprotein lipase and other proteins, angiogenesis, viral invasion, and tumor metastasis.<sup id="cite_ref-Rabenstein_13-1" class="reference"><a href="#cite_note-Rabenstein-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></dd></dl> <p>CSGAGs interact with heparin binding proteins, specifically dermatan sulfate interactions with fibroblast growth factor FGF-2 and FGF-7 have been implicated in cellular proliferation and wound repair<sup id="cite_ref-Trowbridge_16-0" class="reference"><a href="#cite_note-Trowbridge-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> while interactions with hepatic growth factor/scatter factor (HGF/SF) activate the HGF/SF signaling pathway (<a href="/wiki/C-Met" class="mw-redirect" title="C-Met">c-Met</a>) through its receptor. CSGAGs are important in providing support and adhesiveness in bone, skin, and cartilage. Other biological functions for which CSGAGs are known to play critical functions in include inhibition of axonal growth and regeneration in CNS development, roles in brain development, neuritogenic activity, and pathogen infection.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dt>Keratan sulfates</dt> <dd>One of the main functions of the third class of GAGs, keratan sulfates, is the maintenance of tissue hydration.<sup id="cite_ref-Funderburgh3_18-0" class="reference"><a href="#cite_note-Funderburgh3-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Keratan sulfates are in the bone, cartilage, and the cornea of the eye.<sup id="cite_ref-:0_19-0" class="reference"><a href="#cite_note-:0-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Within the normal cornea, dermatan sulfate is fully hydrated whereas keratan sulfate is only partially hydrated suggesting that keratan sulfate may behave as a dynamically controlled buffer for hydration.<sup id="cite_ref-Funderburgh3_18-1" class="reference"><a href="#cite_note-Funderburgh3-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In disease states such as <a href="/wiki/Macular_corneal_dystrophy" title="Macular corneal dystrophy">macular corneal dystrophy</a>, in which GAGs levels such as KS are altered, loss of hydration within the corneal stroma is believed to be the cause of corneal haze, thus supporting the long-held hypothesis that corneal transparency is dependent on proper levels of keratan sulfate. Keratan sulfate GAGs are found in many other tissues besides the cornea, where they are known to regulate <a href="/wiki/Macrophage" title="Macrophage">macrophage</a> adhesion, form barriers to <a href="/wiki/Neurite" title="Neurite">neurite</a> growth, regulate <a href="/wiki/Embryo_implantation" class="mw-redirect" title="Embryo implantation">embryo implantation</a> in the endometrial uterine lining during menstrual cycles, and affect the motility of corneal endothelial cells.<sup id="cite_ref-Funderburgh3_18-2" class="reference"><a href="#cite_note-Funderburgh3-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In summary, KS plays an anti-adhesive role, which suggests very important functions of KS in cell motility and attachment as well as other potential biological processes.</dd></dl> <p><b>Dermatan sulfates</b> </p><p>Dermatan sulfates function in the skin, tendons, blood vessels, and heart valves.<sup id="cite_ref-:0_19-1" class="reference"><a href="#cite_note-:0-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <dl><dt>Hyaluronic acid</dt> <dd><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a> is a major component of <a href="/wiki/Synovial_membrane" title="Synovial membrane">synovial tissues</a> and <a href="/wiki/Synovial_fluid" title="Synovial fluid">fluid</a>, as well as the <a href="/wiki/Ground_substance" title="Ground substance">ground substance</a> of other connective tissues. Hyaluronic acid binds cells together, lubricates joints, and helps maintain the shape of the eyeballs.<sup id="cite_ref-:0_19-2" class="reference"><a href="#cite_note-:0-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Viscoelasticity" title="Viscoelasticity">viscoelasticity</a> of hyaluronic acid makes it ideal for lubricating joints and surfaces that move along each other, such as cartilage. A solution of hyaluronic acid under low <a href="/wiki/Shear_stress" title="Shear stress">shear stress</a> has a much higher viscosity than while under high shear stress.<sup id="cite_ref-Laurent_20-0" class="reference"><a href="#cite_note-Laurent-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hyaluronidase" title="Hyaluronidase">Hyaluronidase</a>, an enzyme produced by white blood cells, sperms cells, and some bacteria, breaks apart the hyaluronic acid, causing the solution to become more liquid.<sup id="cite_ref-:0_19-3" class="reference"><a href="#cite_note-:0-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></dd> <dd><i>In vivo</i>, hyaluronic acid forms randomly kinked coils that entangle to form a hyaluronan network, slowing diffusion and forming a diffusion barrier that regulates transport of substances between cells. For example, hyaluronan helps partition plasma proteins between vascular and extravascular spaces, which affects solubility of macromolecules in the interstitium, changes chemical equilibria, and stabilizes the structure of collagen fibers.<sup id="cite_ref-Laurent_20-1" class="reference"><a href="#cite_note-Laurent-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></dd> <dd>Other functions include matrix interactions with hyaluronan binding proteins such as hyaluronectin, glial hyaluronan binding protein, brain enriched hyaluronan binding protein, <a href="/wiki/Collagen_VI" title="Collagen VI">collagen VI</a>, <a href="/wiki/TSG-6" title="TSG-6">TSG-6</a>, and <a href="/wiki/Inter-alpha-trypsin_inhibitor" title="Inter-alpha-trypsin inhibitor">inter-alpha-trypsin inhibitor</a>. Cell surface interactions involving hyaluronan are its well-known coupling with <a href="/wiki/CD44" title="CD44">CD44</a>, which may be related to tumor progression, and also with RHAMM (<a href="/wiki/Hyaluronan-mediated_motility_receptor" title="Hyaluronan-mediated motility receptor">Hyaluronan-mediated motility receptor</a>), which has been implicated in developmental processes, tumor metastasis, and pathological reparative processes.</dd> <dd>Fibroblasts, mesothelial cells, and certain types of stem cells surround themselves in a <a href="/wiki/Glycocalyx" title="Glycocalyx">pericellular "coat"</a>, part of which is constructed from hyaluronan, in order to shield themselves from bacteria, red blood cells, or other matrix molecules. For example, in regard to stem cells, hyaluronan, along with chondroitin sulfate, helps to form the <a href="/wiki/Stem_cell_niche" class="mw-redirect" title="Stem cell niche">stem cell niche</a>. Stem cells are protected from the effects of growth factors by a shield of hyaluronan and minimally sulfated chondroitin sulfate. During progenitor division, the daughter cell moves outside of this pericellular shield where it can then be influenced by growth factors to differentiate even further.</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=6" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Members of the glycosaminoglycan family vary in the type of hexosamine, hexose or hexuronic acid unit they contain (e.g. <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>, <a href="/wiki/Iduronic_acid" title="Iduronic acid">iduronic acid</a>, <a href="/wiki/Galactose" title="Galactose">galactose</a>, <a href="/wiki/Galactosamine" title="Galactosamine">galactosamine</a>, <a href="/wiki/Glucosamine" title="Glucosamine">glucosamine</a>). </p><p>They also vary in the geometry of the <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic linkage</a>. </p><p>Examples of GAGs include: </p> <table class="wikitable"> <tbody><tr> <th><b>Name</b></th> <th><b>Hexuronic acid or<br />hexose (for keratan)</b></th> <th><b>Hexosamine</b></th> <th><b>Linkage geometry between predominant monomeric units</b></th> <th><b>Unique features</b> </th></tr> <tr valign="top"> <td><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></td> <td>GlcUA or<br />GlcUA(2S)</td> <td>GalNAc or<br />GalNAc(4S) or<br />GalNAc(6S) or<br />GalNAc(4S,6S)</td> <td>GlcUA<i>β</i>(1→3)GalNAc<i>β</i>(1→4)</td> <td>Most prevalent GAG </td></tr> <tr valign="top"> <td><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a></td> <td>GlcUA or<br />IdoUA or<br />IdoUA(2S)</td> <td>GalNAc or<br />GalNAc(4S) or<br />GalNAc(6S) or<br />GalNAc(4S,6S)</td> <td>'<i><b>IdoUA</b></i>β<i>1-3'</i>GalNAc<b><i>β</i>1-4</b></td> <td>Distinguished from chondroitin sulfate by the presence of <a href="/wiki/Iduronic_acid" title="Iduronic acid">iduronic acid</a>, although some hexuronic acid monosaccharides may be <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>.<sup id="cite_ref-Trowbridge_16-1" class="reference"><a href="#cite_note-Trowbridge-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </td></tr> <tr valign="top"> <td><a href="/wiki/Keratan_sulfate" title="Keratan sulfate">Keratan sulfate</a></td> <td>Gal or<br />Gal(6S)</td> <td>GlcNAc or<br />GlcNAc(6S)</td> <td><b>-</b>Gal(6S)<b><i>β</i>1-4</b>GlcNAc(6S)<b><i>β</i>1-3</b></td> <td>Keratan sulfate type II may be <a href="/wiki/Fucose" title="Fucose">fucosylated</a>.<sup id="cite_ref-funderburgh_21-0" class="reference"><a href="#cite_note-funderburgh-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </td></tr> <tr valign="top"> <td><a href="/wiki/Heparin" title="Heparin">Heparin</a></td> <td>GlcUA or<br />IdoUA(2S)</td> <td>GlcNAc or<br />GlcNS or<br />GlcNAc(6S) or<br />GlcNS(6S)</td> <td><b>-</b>IdoUA(2S)<b><i>α</i>1-4</b>GlcNS(6S)<b><i>α</i>1-4</b></td> <td>Highest negative charge density of any known biological molecule </td></tr> <tr valign="top"> <td><a href="/wiki/Heparan_sulfate" title="Heparan sulfate">Heparan sulfate</a></td> <td>GlcUA or<br />IdoUA or<br />IdoUA(2S)</td> <td>GlcNAc or<br />GlcNS or<br />GlcNAc(6S) or<br />GlcNS(6S)</td> <td><b>-</b>GlcUA<b><i>β</i>1-4</b>GlcNAc<b><i>α</i>1-4</b></td> <td>Highly similar in structure to heparin, however heparan sulfate's disaccharide units are organised into distinct sulfated and non-sulfated domains.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </td></tr> <tr valign="top"> <td><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronan</a></td> <td>GlcUA</td> <td>GlcNAc</td> <td><b>-</b>GlcUA<b><i>β</i>1-3</b>GlcNAc<b><i>β</i>1-4</b></td> <td>The only GAG that is exclusively non-sulfated </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Abbreviations">Abbreviations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=7" title="Edit section: Abbreviations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><b>GlcUA</b> = <i>β</i>-D-<a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a></li> <li><b>GlcUA(2S)</b> = 2-O-sulfo-<i>β</i>-D-glucuronic acid</li> <li><b>IdoUA</b> = <i>α</i>-L-<a href="/wiki/Iduronic_acid" title="Iduronic acid">iduronic acid</a></li> <li><b>IdoUA(2S)</b> = 2-O-sulfo-<i>α</i>-L-iduronic acid</li> <li><b>Gal</b> = <i>β</i>-D-<a href="/wiki/Galactose" title="Galactose">galactose</a></li> <li><b>Gal(6S)</b> = 6-O-sulfo-<i>β</i>-D-galactose</li> <li><b>GalNAc</b> = <i>β</i>-D-<a href="/wiki/N-Acetylgalactosamine" title="N-Acetylgalactosamine">N-acetylgalactosamine</a></li> <li><b>GalNAc(4S)</b> = <i>β</i>-D-N-acetylgalactosamine-4-O-sulfate</li> <li><b>GalNAc(6S)</b> = <i>β</i>-D-N-acetylgalactosamine-6-O-sulfate</li> <li><b>GalNAc(4S,6S)</b> = <i>β</i>-D-N-acetylgalactosamine-4-O, 6-O-sulfate</li> <li><b>GlcNAc</b> = <i>α</i>-D-<a href="/wiki/N-Acetylglucosamine" title="N-Acetylglucosamine">N-acetylglucosamine</a></li> <li><b>GlcNS</b> = <i>α</i>-D-N-sulfoglucosamine</li> <li><b>GlcNS(6S)</b> = <i>α</i>-D-N-sulfoglucosamine-6-O-sulfate</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=Glycosaminoglycan&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/Glycoprotein" title="Glycoprotein">Glycoprotein</a> – Protein with oligosaccharide modifications</li> <li><a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">Lipopolysaccharide</a> – Class of molecules found in the outer membrane of gram-negative bacteria</li> <li><a href="/wiki/Snail_slime" title="Snail slime">Snail slime</a> – External bodily secretion produced by snails</li> <li><a href="/wiki/Glycocalyx" title="Glycocalyx">Glycocalyx</a> – Viscous, carbohydrate rich layer at the outermost periphery of a cell. Pericellular coat.</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=Glycosaminoglycan&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 reflist-columns references-column-width reflist-columns-2"> <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"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090628224336/http://www.mercksource.com/pp/us/cns/cns_hl_dorlands_split.jsp?pg=/ppdocs/us/common/dorlands/dorland/four/000045487.htm">"glycosaminoglycan"</a> at <i><a href="/wiki/Dorland%27s_medical_reference_works" title="Dorland's medical reference works">Dorland's Medical Dictionary</a></i></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"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090628224336/http://www.mercksource.com/pp/us/cns/cns_hl_dorlands_split.jsp?pg=/ppdocs/us/common/dorlands/dorland/five/000067915.htm">"mucopolysaccharide"</a> at <i><a href="/wiki/Dorland%27s_medical_reference_works" title="Dorland's medical reference works">Dorland's Medical Dictionary</a></i></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><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="CITEREFEskoKimataLindahl2009" class="citation book cs1">Esko, Jeffrey D; Kimata, Koji; Lindahl, Ulf (2009). "Chapter 16: Proteoglycans and Sulfated Glycosaminoglycans". <i>Essentials of Glycobiology</i>. Cold Spring Harbor Laboratory Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0879695590" title="Special:BookSources/978-0879695590"><bdi>978-0879695590</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+16%3A+Proteoglycans+and+Sulfated+Glycosaminoglycans&rft.btitle=Essentials+of+Glycobiology&rft.pub=Cold+Spring+Harbor+Laboratory+Press&rft.date=2009&rft.isbn=978-0879695590&rft.aulast=Esko&rft.aufirst=Jeffrey+D&rft.au=Kimata%2C+Koji&rft.au=Lindahl%2C+Ulf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosaminoglycan" 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="CITEREFDeAngelis2002" class="citation journal cs1">DeAngelis, Paul L. 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Danvers, MA. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-34500-9" title="Special:BookSources/978-1-118-34500-9"><bdi>978-1-118-34500-9</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/871018672">871018672</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+anatomy+%26+physiology&rft.place=Danvers%2C+MA&rft.edition=14th&rft.date=2013-12-31&rft_id=info%3Aoclcnum%2F871018672&rft.isbn=978-1-118-34500-9&rft.au=Tortora%2C+Gerard+J.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fprinciplesofanat0000tort&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosaminoglycan" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-Laurent-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-Laurent_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Laurent_20-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLaurentLaurentFraser1996" class="citation journal cs1">Laurent TC, Laurent UB, Fraser JR (1996). "The structure and function of hyaluronan: An overview". <i>Immunology and Cell Biology</i>. <b>74</b> (2): A1-7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Ficb.1996.32">10.1038/icb.1996.32</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8724014">8724014</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Immunology+and+Cell+Biology&rft.atitle=The+structure+and+function+of+hyaluronan%3A+An+overview.&rft.volume=74&rft.issue=2&rft.pages=A1-7&rft.date=1996&rft_id=info%3Adoi%2F10.1038%2Ficb.1996.32&rft_id=info%3Apmid%2F8724014&rft.aulast=Laurent&rft.aufirst=TC&rft.au=Laurent%2C+UB&rft.au=Fraser%2C+JR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosaminoglycan" class="Z3988"></span></span> </li> <li id="cite_note-funderburgh-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-funderburgh_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFunderburgh_JL.2000" class="citation journal cs1">Funderburgh JL. (2000). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fglycob%2F10.10.951">"Keratan sulfate: structure, biosynthesis, and function"</a>. <i>Glycobiology</i>. <b>10</b> (10): 951–58. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fglycob%2F10.10.951">10.1093/glycob/10.10.951</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/11030741">11030741</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Glycobiology&rft.atitle=Keratan+sulfate%3A+structure%2C+biosynthesis%2C+and+function&rft.volume=10&rft.issue=10&rft.pages=951-58&rft.date=2000&rft_id=info%3Adoi%2F10.1093%2Fglycob%2F10.10.951&rft_id=info%3Apmid%2F11030741&rft.au=Funderburgh+JL.&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fglycob%252F10.10.951&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosaminoglycan" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGallagher,_J.T.,_Lyon,_M.2000" class="citation book cs1">Gallagher, J.T., Lyon, M. (2000). "Molecular structure of Heparan Sulfate and interactions with growth factors and morphogens". In Iozzo, M, V. (ed.). <i>Proteoglycans: structure, biology and molecular interactions</i>. New York: Marcel Dekker Inc. pp. 27–59. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8247-0334-9" title="Special:BookSources/978-0-8247-0334-9"><bdi>978-0-8247-0334-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Molecular+structure+of+Heparan+Sulfate+and+interactions+with+growth+factors+and+morphogens&rft.btitle=Proteoglycans%3A+structure%2C+biology+and+molecular+interactions&rft.place=New+York&rft.pages=27-59&rft.pub=Marcel+Dekker+Inc.&rft.date=2000&rft.isbn=978-0-8247-0334-9&rft.au=Gallagher%2C+J.T.%2C+Lyon%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycosaminoglycan" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycosaminoglycan&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>King M. 2005. <a rel="nofollow" class="external text" href="http://web.indstate.edu/thcme/mwking/glycans.html">Glycosaminoglycans</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230208165627/https://web.indstate.edu/thcme/mwking/glycans.html">Archived</a> 2023-02-08 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. <a href="/wiki/Indiana_University_School_of_Medicine" title="Indiana University School of Medicine">Indiana University School of Medicine</a> Accessed December 31, 2006.</li> <li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Glycosaminoglycans">Glycosaminoglycans</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li> <li><a rel="nofollow" class="external text" href="http://www.melbourneradiology.com.au/mri-gallery/mri-dgemric-evaluation-of-cartilage.html">MRI evaluation of glycosaminoglycan loss (dGEMRIC evaluation)</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20110822035119/http://www.melbourneradiology.com.au/mri-gallery/mri-dgemric-evaluation-of-cartilage.html">Archived</a> 2011-08-22 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist 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<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" 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 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="Polysaccharides:_glycosaminoglycans" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:LightGray"><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:Glycosaminoglycans" title="Template:Glycosaminoglycans"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycosaminoglycans" title="Template talk:Glycosaminoglycans"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycosaminoglycans" title="Special:EditPage/Template:Glycosaminoglycans"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polysaccharides:_glycosaminoglycans" style="font-size:114%;margin:0 4em"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a>: <a class="mw-selflink selflink">glycosaminoglycans</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Unsulfated, extracellular</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/Hyaluronan" class="mw-redirect" title="Hyaluronan">Hyaluronan</a></li> <li><a href="/wiki/Sodium_hyaluronate" title="Sodium hyaluronate">Sodium hyaluronate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Sulfated, extracellular</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/Chondroitin" title="Chondroitin">Chondroitin</a> <ul><li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></li> <li><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a></li></ul></li> <li><a href="/wiki/Heparan_sulfate" title="Heparan sulfate">Heparan sulfate</a></li> <li><a href="/wiki/Keratan_sulfate" title="Keratan sulfate">Keratan sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Sulfated, intracellular</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/Heparin" title="Heparin">Heparin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Synthetic</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/Polysulfated_glycosaminoglycan" title="Polysulfated glycosaminoglycan">Polysulfated glycosaminoglycan</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 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