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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Glycans_and_proteins" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glycans_and_proteins"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Glycans and proteins</span> </div> </a> <button aria-controls="toc-Glycans_and_proteins-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Glycans and proteins subsection</span> </button> <ul id="toc-Glycans_and_proteins-sublist" class="vector-toc-list"> <li id="toc-N-Linked_glycans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#N-Linked_glycans"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span><i>N</i>-Linked glycans</span> </div> </a> <ul id="toc-N-Linked_glycans-sublist" class="vector-toc-list"> <li id="toc-Introduction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Introduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.1</span> <span>Introduction</span> </div> </a> <ul id="toc-Introduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Assembly" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Assembly"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.2</span> <span>Assembly</span> </div> </a> <ul id="toc-Assembly-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Processing,_modification,_and_diversity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Processing,_modification,_and_diversity"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.3</span> <span>Processing, modification, and diversity</span> </div> </a> <ul id="toc-Processing,_modification,_and_diversity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Functions_and_importance" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Functions_and_importance"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.4</span> <span>Functions and importance</span> </div> </a> <ul id="toc-Functions_and_importance-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-O-Linked_glycans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#O-Linked_glycans"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span><i>O</i>-Linked glycans</span> </div> </a> <ul id="toc-O-Linked_glycans-sublist" class="vector-toc-list"> <li id="toc-Introduction_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Introduction_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2.1</span> <span>Introduction</span> </div> </a> <ul id="toc-Introduction_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Assembly_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Assembly_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2.2</span> <span>Assembly</span> </div> </a> <ul id="toc-Assembly_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Functions_and_importance_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Functions_and_importance_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2.3</span> <span>Functions and importance</span> </div> </a> <ul id="toc-Functions_and_importance_2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Glycosaminoglycans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glycosaminoglycans"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Glycosaminoglycans</span> </div> </a> <ul id="toc-Glycosaminoglycans-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Glycoscience" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glycoscience"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Glycoscience</span> </div> </a> <ul id="toc-Glycoscience-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Glycans_and_lipids" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Glycans_and_lipids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Glycans and lipids</span> </div> </a> <ul id="toc-Glycans_and_lipids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-GPI-Anchors" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#GPI-Anchors"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>GPI-Anchors</span> </div> </a> <ul id="toc-GPI-Anchors-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tools_used_for_glycan_research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Tools_used_for_glycan_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Tools used for glycan research</span> </div> </a> <button aria-controls="toc-Tools_used_for_glycan_research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Tools used for glycan research subsection</span> </button> <ul id="toc-Tools_used_for_glycan_research-sublist" class="vector-toc-list"> <li id="toc-High-resolution_mass_spectrometry_(MS)_and_high-performance_liquid_chromatography_(HPLC)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#High-resolution_mass_spectrometry_(MS)_and_high-performance_liquid_chromatography_(HPLC)"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>High-resolution mass spectrometry (MS) and high-performance liquid chromatography (HPLC)</span> </div> </a> <ul id="toc-High-resolution_mass_spectrometry_(MS)_and_high-performance_liquid_chromatography_(HPLC)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Multiple_reaction_monitoring_(MRM)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Multiple_reaction_monitoring_(MRM)"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Multiple reaction monitoring (MRM)</span> </div> </a> <ul id="toc-Multiple_reaction_monitoring_(MRM)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Arrays" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Arrays"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Arrays</span> </div> </a> <ul id="toc-Arrays-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolic_and_covalent_labeling_of_glycans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolic_and_covalent_labeling_of_glycans"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Metabolic and covalent labeling of glycans</span> </div> </a> <ul id="toc-Metabolic_and_covalent_labeling_of_glycans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tools_for_glycoproteins" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Tools_for_glycoproteins"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Tools for glycoproteins</span> </div> </a> <ul id="toc-Tools_for_glycoproteins-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">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Resources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Resources"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Resources</span> </div> </a> <ul id="toc-Resources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input 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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href="https://bg.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D0%BA%D0%B0%D0%BD" title="Гликан – Bulgarian" lang="bg" hreflang="bg" data-title="Гликан" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Glikan" title="Glikan – Bosnian" lang="bs" hreflang="bs" data-title="Glikan" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca badge-Q70893996 mw-list-item" title=""><a href="https://ca.wikipedia.org/wiki/Glican" title="Glican – Catalan" lang="ca" hreflang="ca" data-title="Glican" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</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%D8%A7%D9%86" title="گلیکان – Persian" lang="fa" hreflang="fa" data-title="گلیکان" 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/Glycane" title="Glycane – French" lang="fr" hreflang="fr" data-title="Glycane" 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/Glicano" title="Glicano – Galician" lang="gl" hreflang="gl" data-title="Glicano" 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%B9%B8" title="글리칸 – Korean" lang="ko" hreflang="ko" data-title="글리칸" 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/Glikan" title="Glikan – Indonesian" lang="id" hreflang="id" data-title="Glikan" 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/Glicani" title="Glicani – Italian" lang="it" hreflang="it" data-title="Glicani" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%B3%96%E9%8E%96" title="糖鎖 – Japanese" lang="ja" hreflang="ja" data-title="糖鎖" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Glicano" title="Glicano – Portuguese" lang="pt" hreflang="pt" data-title="Glicano" 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/Glican" title="Glican – Romanian" lang="ro" hreflang="ro" data-title="Glican" 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%B0%D0%BD%D1%8B" title="Гликаны – Russian" lang="ru" hreflang="ru" data-title="Гликаны" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Glikan" title="Glikan – Serbian" lang="sr" hreflang="sr" data-title="Glikan" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Glykaani" title="Glykaani – Finnish" lang="fi" hreflang="fi" data-title="Glykaani" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Glikan" title="Glikan – Turkish" lang="tr" hreflang="tr" data-title="Glikan" data-language-autonym="Türkçe" 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role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Glycan" title="Special:EditPage/Glycan">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Glycan%22">"Glycan"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Glycan%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Glycan%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Glycan%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Glycan%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Glycan%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">May 2012</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> <p>The terms <b>glycans</b> and <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> are defined by <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> as synonyms meaning "compounds consisting of a large number of <a href="/wiki/Monosaccharides" class="mw-redirect" title="Monosaccharides">monosaccharides</a> linked glycosidically".<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> However, in practice the term glycan may also be used to refer to the <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> portion of a <a href="/wiki/Glycoconjugate" title="Glycoconjugate">glycoconjugate</a>, such as a <a href="/wiki/Glycoprotein" title="Glycoprotein">glycoprotein</a>, <a href="/wiki/Glycolipid" title="Glycolipid">glycolipid</a>, or a <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycan</a>, even if the carbohydrate is only an <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharide</a>.<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> Glycans usually consist solely of <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">O-glycosidic linkages</a> of monosaccharides. For example, <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> is a glycan (or, to be more specific, a <a href="/wiki/Glucan" title="Glucan">glucan</a>) composed of β-1,4-linked <small>D</small>-glucose, and <a href="/wiki/Chitin" title="Chitin">chitin</a> is a glycan composed of β-1,4-linked <i>N</i>-acetyl-<small>D</small>-glucosamine. Glycans can be <a href="/wiki/Homopolymer" class="mw-redirect" title="Homopolymer">homo-</a> or <a href="/wiki/Heteropolymer" class="mw-redirect" title="Heteropolymer">heteropolymers</a> of monosaccharide residues, and can be linear or branched. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Glycans_and_proteins">Glycans and proteins</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=1" title="Edit section: Glycans and proteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Glycan-protein_interactions" title="Glycan-protein interactions">Glycan-protein interactions</a></div> <p>Glycans can be found attached to proteins as in glycoproteins and proteoglycans. In general, they are found on the exterior surface of cells. O- and N-linked glycans are very common in <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a> but may also be found, although less commonly, in <a href="/wiki/Prokaryotes" class="mw-redirect" title="Prokaryotes">prokaryotes</a>. </p> <div class="mw-heading mw-heading3"><h3 id="N-Linked_glycans"><i>N</i>-Linked glycans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=2" title="Edit section: N-Linked glycans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/N-linked_glycosylation" title="N-linked glycosylation">N-linked glycosylation</a></div> <div class="mw-heading mw-heading4"><h4 id="Introduction">Introduction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=3" title="Edit section: Introduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>N-Linked glycans are attached in the <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a> to the nitrogen (N) in the side chain of <a href="/wiki/Asparagine" title="Asparagine">asparagine</a> (Asn) in the <a href="/wiki/Sequon" title="Sequon">sequon</a>. The sequon is an Asn-X-Ser or Asn-X-Thr sequence, where X is any <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> except <a href="/wiki/Proline" title="Proline">proline</a> and the glycan may be composed of <a href="/wiki/N-acetylgalactosamine" class="mw-redirect" title="N-acetylgalactosamine"><i>N</i>-acetylgalactosamine</a>, <a href="/wiki/Galactose" title="Galactose">galactose</a>, <a href="/wiki/Neuraminic_acid" title="Neuraminic acid">neuraminic acid</a>, <a href="/wiki/N-acetylglucosamine" class="mw-redirect" title="N-acetylglucosamine"><i>N</i>-acetylglucosamine</a>, <a href="/wiki/Fucose" title="Fucose">fucose</a>, <a href="/wiki/Mannose" title="Mannose">mannose</a>, and other monosaccharides. </p> <div class="mw-heading mw-heading4"><h4 id="Assembly">Assembly</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=4" title="Edit section: Assembly"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In eukaryotes, N-linked glycans are derived from a core 14-<a href="/wiki/Sugar" title="Sugar">sugar</a> unit assembled in the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasm</a> and <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a>. First, two <a href="/wiki/N-Acetylglucosamine" title="N-Acetylglucosamine"><i>N</i>-acetylglucosamine</a> residues are attached to <a href="/wiki/Dolichol_monophosphate" title="Dolichol monophosphate">dolichol monophosphate</a>, a lipid, on the external side of the endoplasmic reticulum membrane. Five mannose residues are then added to this structure. At this point, the partially finished core glycan is flipped across the endoplasmic reticulum membrane, so that it is now located within the reticular lumen. Assembly then continues within the endoplasmic reticulum, with the addition of four more mannose residues. Finally, three glucose residues are added to this structure. Following full assembly, the glycan is transferred en bloc by the <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">glycosyltransferase</a> <a href="/wiki/Oligosaccharyltransferase" title="Oligosaccharyltransferase">oligosaccharyltransferase</a> to a nascent peptide chain, within the reticular lumen. This core structure of N-linked glycans, thus, consists of 14 residues (3 glucose, 9 mannose, and 2 <i>N</i>-acetylglucosamine). </p><p>Image: <a rel="nofollow" class="external free" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.469">https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.469</a> </p><p>Dark squares are <i>N</i>-acetylglucosamine; light circles are mannose; dark triangles are glucose. </p> <div class="mw-heading mw-heading4"><h4 id="Processing,_modification,_and_diversity"><span id="Processing.2C_modification.2C_and_diversity"></span>Processing, modification, and diversity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=5" title="Edit section: Processing, modification, and diversity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Once transferred to the nascent peptide chain, N-linked glycans, in general, undergo extensive processing reactions, whereby the three glucose residues are removed, as well as several mannose residues, depending on the N-linked glycan in question. The removal of the glucose residues is dependent on proper protein folding. These processing reactions occur in the <a href="/wiki/Golgi_apparatus" title="Golgi apparatus">Golgi apparatus</a>. Modification reactions may involve the addition of a phosphate or acetyl group onto the sugars, or the addition of new sugars, such as <a href="/wiki/Neuraminic_acid" title="Neuraminic acid">neuraminic acid</a>. Processing and modification of N-linked glycans within the Golgi does not follow a linear pathway. As a result, many different variations of N-linked glycan structure are possible, depending on enzyme activity in the Golgi. </p> <div class="mw-heading mw-heading4"><h4 id="Functions_and_importance">Functions and importance</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=6" title="Edit section: Functions and importance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>N-linked glycans are extremely important in proper protein folding in eukaryotic cells. <a href="/wiki/Chaperone_(protein)" title="Chaperone (protein)">Chaperone</a> proteins in the endoplasmic reticulum, such as <a href="/wiki/Calnexin" title="Calnexin">calnexin</a> and <a href="/wiki/Calreticulin" title="Calreticulin">calreticulin</a>, bind to the three glucose residues present on the core N-linked glycan. These chaperone proteins then serve to aid in the folding of the protein that the glycan is attached to. Following proper folding, the three glucose residues are removed, and the glycan moves on to further processing reactions. If the protein fails to fold properly, the three glucose residues are reattached, allowing the protein to re-associate with the chaperones. This cycle may repeat several times until a protein reaches its proper conformation. If a protein repeatedly fails to properly fold, it is excreted from the endoplasmic reticulum and degraded by cytoplasmic proteases. </p><p>N-linked glycans also contribute to protein folding by steric effects. For example, <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> residues in the peptide may be temporarily blocked from forming disulfide bonds with other cysteine residues, due to the size of a nearby glycan. Therefore, the presence of a N-linked glycan allows the cell to control which cysteine residues will form disulfide bonds. </p><p>N-linked glycans also play an important role in cell-cell interactions. For example, tumour cells make N-linked glycans that are abnormal. These are recognized by the <a href="/wiki/CD337" class="mw-redirect" title="CD337">CD337</a> receptor on <a href="/wiki/Natural_Killer_cell" class="mw-redirect" title="Natural Killer cell">Natural Killer cells</a> as a sign that the cell in question is cancerous. </p><p>Within the immune system the N-linked glycans on an immune cell's surface will help dictate that migration pattern of the cell, e.g. immune cells that migrate to the skin have specific glycosylations that favor homing to that site.<sup id="cite_ref-immune_glycan_3-0" class="reference"><a href="#cite_note-immune_glycan-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The glycosylation patterns on the various immunoglobulins including IgE, IgM, IgD, IgE, IgA, and IgG bestow them with unique effector functions by altering their affinities for <a href="/wiki/Fragment_crystallizable_region" title="Fragment crystallizable region">Fc</a> and other immune receptors.<sup id="cite_ref-immune_glycan_3-1" class="reference"><a href="#cite_note-immune_glycan-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Glycans may also be involved in "self" and "non self" discrimination, which may be relevant to the pathophysiology of various autoimmune diseases;<sup id="cite_ref-immune_glycan_3-2" class="reference"><a href="#cite_note-immune_glycan-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> including rheumatoid arthritis <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> and type 1 diabetes.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The targeting of degradative <a href="/wiki/Lysosomal" class="mw-redirect" title="Lysosomal">lysosomal</a> enzymes is also accomplished by N-linked glycans. The modification of an N-linked glycan with a <a href="/wiki/Mannose-6-phosphate" class="mw-redirect" title="Mannose-6-phosphate">mannose-6-phosphate</a> residue serves as a signal that the protein to which this glycan is attached should be moved to the lysosome. This recognition and trafficking of lysosomal enzymes by the presence of mannose-6-phosphate is accomplished by two proteins: CI-MPR (cation-independent <a href="/wiki/Mannose_6-phosphate_receptor" title="Mannose 6-phosphate receptor">mannose-6-phosphate receptor</a>) and CD-MPR (cation-dependent mannose-6-phosphate receptor). </p> <div class="mw-heading mw-heading3"><h3 id="O-Linked_glycans"><i>O</i>-Linked glycans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=7" title="Edit section: O-Linked glycans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/O-linked_glycosylation" title="O-linked glycosylation">O-linked glycosylation</a></div> <div class="mw-heading mw-heading4"><h4 id="Introduction_2">Introduction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=8" title="Edit section: Introduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In eukaryotes, <i>O</i>-linked glycans are assembled one sugar at a time on a <a href="/wiki/Serine" title="Serine">serine</a> or <a href="/wiki/Threonine" title="Threonine">threonine</a> residue of a peptide chain in the Golgi apparatus. Unlike <i>N</i>-linked glycans, there is no known <a href="/wiki/Consensus_sequence" title="Consensus sequence">consensus sequence</a> yet. However, the placement of a <a href="/wiki/Proline" title="Proline">proline</a> residue at either -1 or +3 relative to the serine or threonine is favourable for O-linked glycosylation. </p> <div class="mw-heading mw-heading4"><h4 id="Assembly_2">Assembly</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=9" title="Edit section: Assembly"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first monosaccharide attached in the synthesis of <i>O</i>-linked glycans is N-acetyl-galactosamine. After this, several different pathways are possible. A Core 1 structure is generated by the addition of galactose. A Core 2 structure is generated by the addition of N-acetyl-glucosamine to the N-acetyl-galactosamine of the Core 1 structure. Core 3 structures are generated by the addition of a single N-acetyl-glucosamine to the original N-acetyl-galactosamine. Core 4 structures are generated by the addition of a second N-acetyl-glucosamine to the Core 3 structure. Other core structures are possible, though less common. </p><p>Images: </p><p><a rel="nofollow" class="external free" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.561">https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.561</a> : Core 1 and Core 2 generation. White square = N-acetyl-galactosamine; black circle = galactose; Black square = N-acetyl-glucosamine. Note: There is a mistake in this diagram. The bottom square should always be white in each image, not black. </p><p><a rel="nofollow" class="external free" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.562">https://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=glyco.figgrp.562</a> : Core 3 and Core 4 generation. </p><p>A common structural theme in O-linked glycans is the addition of <a href="/w/index.php?title=Polylactosamine&action=edit&redlink=1" class="new" title="Polylactosamine (page does not exist)">polylactosamine</a> units to the various core structures. These are formed by the repetitive addition of galactose and N-acetyl-glucosamine units. Polylactosamine chains on O-linked glycans are often capped by the addition of a <a href="/wiki/Sialic_acid" title="Sialic acid">sialic acid</a> residue (similar to neuraminic acid). If a <a href="/wiki/Fucose" title="Fucose">fucose</a> residue is also added, to the next to penultimate residue, a <a href="/wiki/Sialyl-Lewis_X" title="Sialyl-Lewis X">Sialyl-Lewis X</a> (SLex) structure is formed. </p> <div class="mw-heading mw-heading4"><h4 id="Functions_and_importance_2">Functions and importance</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=10" title="Edit section: Functions and importance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Sialyl_lewis_x" class="mw-redirect" title="Sialyl lewis x">Sialyl lewis x</a> is important in <a href="/wiki/ABO" class="mw-redirect" title="ABO">ABO</a> blood antigen determination. </p><p>SLex is also important to proper immune response. P-<a href="/wiki/Selectin" title="Selectin">selectin</a> release from <a href="/wiki/Weibel%E2%80%93Palade_body" title="Weibel–Palade body">Weibel-Palade bodies</a>, on blood vessel endothelial cells, can be induced by a number of factors. One such factor is the response of the endothelial cell to certain bacterial molecules, such as <a href="/wiki/Peptidoglycan" title="Peptidoglycan">peptidoglycan</a>. P-selectin binds to the SLex structure that is present on <a href="/wiki/Neutrophils" class="mw-redirect" title="Neutrophils">neutrophils</a> in the <a href="/wiki/Bloodstream" class="mw-redirect" title="Bloodstream">bloodstream</a> and helps to mediate the <a href="/wiki/Extravasation" title="Extravasation">extravasation</a> of these cells into the surrounding tissue during infection. </p><p><i>O</i>-linked glycans, in particular <a href="/wiki/Mucin" title="Mucin">mucin</a>, have been found to be important in developing normal intestinal microflora. Certain strains of intestinal bacteria bind specifically to mucin, allowing them to colonize the intestine. </p><p>Examples of <i>O</i>-linked <a href="/wiki/Glycoprotein" title="Glycoprotein">glycoproteins</a> are: </p> <ul><li><a href="/wiki/Glycophorin" title="Glycophorin">Glycophorin</a>, a protein in <a href="/wiki/Erythrocyte" class="mw-redirect" title="Erythrocyte">erythrocyte</a> <a href="/wiki/Cell_membranes" class="mw-redirect" title="Cell membranes">cell membranes</a></li> <li>Mucin, a protein in <a href="/wiki/Saliva" title="Saliva">saliva</a> involved in formation of <a href="/wiki/Dental_plaque" title="Dental plaque">dental plaque</a></li> <li><a href="/wiki/Notch_signaling" class="mw-redirect" title="Notch signaling">Notch</a>, a transmembrane receptor involved in development and cell fate decisions</li> <li><a href="/wiki/Thrombospondin" title="Thrombospondin">Thrombospondin</a></li> <li><a href="/wiki/Factor_VII" title="Factor VII">Factor VII</a></li> <li><a href="/wiki/Factor_IX" title="Factor IX">Factor IX</a></li> <li>Urinary type <a href="/wiki/Plasminogen_activator" title="Plasminogen activator">plasminogen activator</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Glycosaminoglycans">Glycosaminoglycans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=11" title="Edit section: Glycosaminoglycans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">Glycosaminoglycan</a></div> <p>Another type of cellular glycan is the <a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">glycosaminoglycans</a> (GAGs). These comprise 2-aminosugars linked in an alternating fashion with <a href="/wiki/Uronic_acid" title="Uronic acid">uronic acids</a>, and include polymers such as <a href="/wiki/Heparin" title="Heparin">heparin</a>, <a href="/wiki/Heparan_sulfate" title="Heparan sulfate">heparan sulfate</a>, <a href="/wiki/Chondroitin" title="Chondroitin">chondroitin</a>, <a href="/wiki/Keratan" class="mw-redirect" title="Keratan">keratan</a> and <a href="/wiki/Dermatan" class="mw-redirect" title="Dermatan">dermatan</a>. Some glycosaminoglycans, such as heparan sulfate, are found attached to the cell surface, where they are linked through a tetrasacharide linker via a <a href="/wiki/Xylosyl" class="mw-redirect" title="Xylosyl">xylosyl</a> residue to a protein (forming a <a href="/wiki/Glycoprotein" title="Glycoprotein">glycoprotein</a> or <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycan</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Glycoscience">Glycoscience</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=12" title="Edit section: Glycoscience"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2012 report from the <a href="/wiki/U.S._National_Research_Council" class="mw-redirect" title="U.S. National Research Council">U.S. National Research Council</a> calls for a new focus on glycoscience, a field that explores the structures and functions of glycans and promises great advances in areas as diverse as medicine, energy generation, and materials science.<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> Until now, glycans have received little attention from the research community due to a lack of tools to probe their often complex structures and properties.<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> The report presents a roadmap for transforming glycoscience from a field dominated by specialists to a widely studied and integrated discipline. </p> <div class="mw-heading mw-heading2"><h2 id="Glycans_and_lipids">Glycans and lipids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=13" title="Edit section: Glycans and lipids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>See <a href="/wiki/Glycolipids" class="mw-redirect" title="Glycolipids">glycolipids</a> </p> <div class="mw-heading mw-heading2"><h2 id="GPI-Anchors">GPI-Anchors</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=14" title="Edit section: GPI-Anchors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>See <a href="/wiki/Glycophosphatidylinositol" class="mw-redirect" title="Glycophosphatidylinositol">glycophosphatidylinositol</a> </p> <div class="mw-heading mw-heading2"><h2 id="Tools_used_for_glycan_research">Tools used for glycan research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=15" title="Edit section: Tools used for glycan research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following are examples of the commonly used techniques in glycan analysis:<sup id="cite_ref-Cold_Spring_Harbor_Laboratory_Press_8-0" class="reference"><a href="#cite_note-Cold_Spring_Harbor_Laboratory_Press-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><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="High-resolution_mass_spectrometry_(MS)_and_high-performance_liquid_chromatography_(HPLC)"><span id="High-resolution_mass_spectrometry_.28MS.29_and_high-performance_liquid_chromatography_.28HPLC.29"></span>High-resolution mass spectrometry (MS) and high-performance liquid chromatography (HPLC)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=16" title="Edit section: High-resolution mass spectrometry (MS) and high-performance liquid chromatography (HPLC)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most commonly applied methods are <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">MS</a> and <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a>, in which the glycan part is cleaved either enzymatically or chemically from the target and subjected to analysis.<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> In case of glycolipids, they can be analyzed directly without separation of the lipid component. </p><p>N-<a href="/wiki/Glycans" class="mw-redirect" title="Glycans">glycans</a> from glycoproteins are analyzed routinely by high-performance-liquid-chromatography (reversed phase, normal phase and ion exchange HPLC) after tagging the reducing end of the sugars with a fluorescent compound (reductive labeling).<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> A large variety of different labels were introduced in the recent years, where 2-aminobenzamide (AB), anthranilic acid (AA), 2-aminopyridin (PA), 2-aminoacridone (AMAC) and 3-(acetylamino)-6-aminoacridine (AA-Ac) are just a few of them.<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> Different labels have to be used for different ESI modes and MS systems used. <sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>O-<a href="/wiki/Glycans" class="mw-redirect" title="Glycans">glycans</a> are usually analysed without any tags, due to the chemical release conditions preventing them to be labeled. </p><p>Fractionated glycans from <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> (HPLC) instruments can be further analyzed by <a href="/wiki/MALDI" class="mw-redirect" title="MALDI">MALDI</a>-TOF-MS(MS) to get further information about structure and purity. Sometimes glycan pools are analyzed directly by <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> without prefractionation, although a discrimination between isobaric glycan structures is more challenging or even not always possible. Anyway, direct <a href="/wiki/MALDI" class="mw-redirect" title="MALDI">MALDI</a>-TOF-MS analysis can lead to a fast and straightforward illustration of the glycan pool.<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><p>In recent years, high performance liquid chromatography online coupled to mass spectrometry became very popular. By choosing porous graphitic carbon as a stationary phase for liquid chromatography, even non derivatized glycans can be analyzed. Detection is here done by mass spectrometry, but in instead of <a href="/wiki/MALDI" class="mw-redirect" title="MALDI">MALDI</a>-MS, electrospray ionisation (<a href="/wiki/Electrospray_ionization" title="Electrospray ionization">ESI</a>) is more frequently used.<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><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><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> <div class="mw-heading mw-heading3"><h3 id="Multiple_reaction_monitoring_(MRM)"><span id="Multiple_reaction_monitoring_.28MRM.29"></span>Multiple reaction monitoring (MRM)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=17" title="Edit section: Multiple reaction monitoring (MRM)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although MRM has been used extensively in metabolomics and proteomics, its high sensitivity and linear response over a wide dynamic range make it especially suited for glycan biomarker research and discovery. MRM is performed on a triple quadrupole (QqQ) instrument, which is set to detect a predetermined precursor ion in the first quadrupole, a fragmented in the collision quadrupole, and a predetermined fragment ion in the third quadrupole. It is a non-scanning technique, wherein each transition is detected individually and the detection of multiple transitions occurs concurrently in duty cycles. This technique is being used to characterize the immune glycome.<sup id="cite_ref-immune_glycan_3-3" class="reference"><a href="#cite_note-immune_glycan-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><b>Table 1</b>:Advantages and disadvantages of mass spectrometry in glycan analysis </p> <table class="wikitable" border="1"> <tbody><tr> <th><b>Advantages</b> </th> <th><b>Disadvantages</b> </th></tr> <tr> <td> <ul><li>Applicable for small sample amounts (lower fmol range)</li> <li>Useful for complex glycan mixtures (generation of a further analysis dimension).</li> <li>Attachment sides can be analysed by tandem MS experiments (side-specific glycan analysis).</li> <li>Glycan sequencing by tandem MS experiments.</li></ul> </td> <td> <ul><li>Destructive method.</li> <li>Need of a proper experimental design.</li></ul> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Arrays">Arrays</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=18" title="Edit section: Arrays"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lectin and antibody arrays provide high-throughput screening of many samples containing glycans. This method uses either naturally occurring <a href="/wiki/Lectins" class="mw-redirect" title="Lectins">lectins</a> or artificial <a href="/wiki/Monoclonal_antibodies" class="mw-redirect" title="Monoclonal antibodies">monoclonal antibodies</a>, where both are immobilized on a certain chip and incubated with a fluorescent glycoprotein sample. </p><p>Glycan arrays, like that offered by the <a href="/wiki/Consortium_for_Functional_Glycomics" title="Consortium for Functional Glycomics">Consortium for Functional Glycomics</a> and <a rel="nofollow" class="external text" href="http://www.zbiotech.com/">Z Biotech LLC</a>, contain carbohydrate compounds that can be screened with lectins or antibodies to define carbohydrate specificity and identify ligands. </p> <div class="mw-heading mw-heading3"><h3 id="Metabolic_and_covalent_labeling_of_glycans">Metabolic and covalent labeling of glycans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=19" title="Edit section: Metabolic and covalent labeling of glycans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metabolic labeling of glycans can be used as a way to detect glycan structures. A well-known strategy involves the use of <a href="/wiki/Azide" title="Azide">azide</a>-labeled sugars which can be reacted using the <a href="/wiki/Staudinger_ligation" class="mw-redirect" title="Staudinger ligation">Staudinger ligation</a>. This method has been used for in vitro and in vivo imaging of glycans. </p> <div class="mw-heading mw-heading3"><h3 id="Tools_for_glycoproteins">Tools for glycoproteins</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=20" title="Edit section: Tools for glycoproteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> and <a href="/wiki/Protein_nuclear_magnetic_resonance_spectroscopy" class="mw-redirect" title="Protein nuclear magnetic resonance spectroscopy">nuclear magnetic resonance (NMR) spectroscopy</a> for complete structural analysis of complex glycans is a difficult and complex field. However, the structure of the binding site of numerous <a href="/wiki/Lectin" title="Lectin">lectins</a>, <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> and other carbohydrate-binding proteins have revealed a wide variety of the structural basis for glycome function. The purity of test samples have been obtained through <a href="/wiki/Chromatography" title="Chromatography">chromatography</a> (<a href="/wiki/Affinity_chromatography" title="Affinity chromatography">affinity chromatography</a> etc.) and analytical <a href="/wiki/Electrophoresis" title="Electrophoresis">electrophoresis</a> (<a href="/wiki/PAGE" class="mw-redirect" title="PAGE">PAGE (polyacrylamide electrophoresis)</a>, <a href="/wiki/Capillary_electrophoresis" title="Capillary electrophoresis">capillary electrophoresis</a>, <a href="/wiki/Affinity_electrophoresis" title="Affinity electrophoresis">affinity electrophoresis</a>, etc.). </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=21" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Glycoside" title="Glycoside">Glycoside</a></li> <li><a href="/wiki/Glycoside_hydrolase" title="Glycoside hydrolase">Glycoside hydrolase</a></li> <li><a href="/wiki/Glycosylation" title="Glycosylation">Glycosylation</a></li> <li><a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">Glycosyltransferase</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Resources">Resources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glycan&action=edit&section=22" title="Edit section: Resources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://research.bidmc.org/ncfg">National Center for Functional Glycomics (NCFG)</a> The focus of the NCFG is the development in the glycosciences, with an emphasis on exploring the molecular mechanisms of glycan recognition by proteins important in human biology and disease. They have a number of <a rel="nofollow" class="external text" href="https://ncfg.hms.harvard.edu/resources">resources for glycan analysis</a> as well as <a rel="nofollow" class="external text" href="https://ncfg.hms.harvard.edu/training">training in glycomics</a> and <a rel="nofollow" class="external text" href="https://ncfg.hms.harvard.edu/protocols">protocols for glycan analysis</a></li> <li><a rel="nofollow" class="external text" href="https://glytoucan.org/">GlyTouCan</a>, Glycan structure repository</li> <li><a rel="nofollow" class="external text" href="http://glycosciences.de/">Glycosciences.DE</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210211160118/http://www.glycosciences.de/">Archived</a> 2021-02-11 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, German glycan database</li> <li><a rel="nofollow" class="external text" href="http://glycoscience.ru">Carbohydrate Structure Database</a>, Russian glycan database</li> <li><a rel="nofollow" class="external text" href="http://unicarbkb.org">UniCarbKB</a>, Australian glycan database</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130703194144/http://glycosuitedb.expasy.org/glycosuite/glycodb">GlycoSuiteDB</a>, glycan database by <a href="/wiki/Swiss_Institute_of_Bioinformatics" title="Swiss Institute of Bioinformatics">Swiss Institute of Bioinformatics</a></li> <li><a rel="nofollow" class="external text" href="https://www.glygen.org/">GlyGen</a>, NIH funded glycoinformatics resource</li> <li>The <a href="/wiki/Consortium_for_Functional_Glycomics" title="Consortium for Functional Glycomics">Consortium for Functional Glycomics</a> (CFG) is a non-profit research initiative comprising eight core facilities and 500+ <a rel="nofollow" class="external text" href="http://www.functionalglycomics.org/glycomics/common/jsp/useraccess/pipeople.jsp">participating investigators</a> that work together to develop <a rel="nofollow" class="external text" href="http://www.functionalglycomics.org/static/consortium/resources.shtml">resources and services</a> and make them available to the scientific community free of charge. The data generated by these resources are captured in databases accessible through the <a rel="nofollow" class="external text" href="http://www.functionalglycomics.org">Functional Glycomics Gateway</a>, a web resource maintained through a partnership between the CFG and <a href="/wiki/Nature_Publishing_Group" class="mw-redirect" title="Nature Publishing Group">Nature Publishing Group</a>.</li> <li><a rel="nofollow" class="external text" href="http://dels.nas.edu/Report/Transforming-Glycoscience-Roadmap/13446">Transforming Glycoscience: A Roadmap for the Future</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141020030759/http://dels.nas.edu/Report/Transforming-Glycoscience-Roadmap/13446">Archived</a> 2014-10-20 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> by the <a href="/wiki/U.S._National_Research_Council" class="mw-redirect" title="U.S. National Research Council">U.S. National Research Council</a>. This site provides information about the <a href="/wiki/U.S._National_Research_Council" class="mw-redirect" title="U.S. National Research Council">U.S. National Research Council</a>'s reports and workshops on glycoscience.</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=Glycan&action=edit&section=23" 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 book cs1"><a rel="nofollow" class="external text" href="http://goldbook.iupac.org/G02645.html">"Glycans"</a>. <i>IUPAC Gold Book - 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Glycoconjugates,_lipids,_and_glycolipids:_sphingolipids_and_glycosphingolipids,_and_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" 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style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cerebroside" title="Cerebroside">Cerebroside</a> <ul><li><a href="/wiki/Galactocerebroside" class="mw-redirect" title="Galactocerebroside">Galactocerebroside</a></li> <li><a href="/wiki/Glucocerebroside" title="Glucocerebroside">Glucocerebroside</a></li></ul></li> <li><a href="/wiki/Sulfatide" title="Sulfatide">Sulfatide</a></li> <li><a href="/wiki/Lactosylceramide" title="Lactosylceramide">Lactosylceramide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Globosides" class="mw-redirect" title="Globosides">Globosides</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/Globotriaosylceramide" title="Globotriaosylceramide">Globotriaosylceramide</a></li> <li><a href="/wiki/Stage-specific_embryonic_antigen_3" title="Stage-specific embryonic antigen 3">Stage-specific embryonic antigen 3</a></li> <li><a href="/wiki/Globo_H" title="Globo H">Globo H</a></li> <li><a href="/wiki/Forssman_antigen" title="Forssman antigen">Forssman antigen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gangliosides" class="mw-redirect" title="Gangliosides">Gangliosides</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/GM1" title="GM1">GM1</a></li> <li><a href="/wiki/GM2_(ganglioside)" title="GM2 (ganglioside)">GM2</a></li> <li><a href="/wiki/GM3" title="GM3">GM3</a></li> <li><a href="/wiki/GD2" title="GD2">GD2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sphingomyelin" title="Sphingomyelin">Sphingomyelin</a></li> <li><a href="/wiki/Sphingosine-1-phosphate" title="Sphingosine-1-phosphate">Sphingosine-1-phosphate</a></li></ul> </div></td></tr></tbody></table></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=Glycan&action=edit&section=24" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEmanual_Maverakis2015" class="citation journal cs1">Emanual Maverakis; et al. (2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4340844">"Glycans in the immune system and The Altered Glycan Theory of Autoimmunity"</a>. <i>Journal of Autoimmunity</i>. <b>57</b>: 1–13. <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.jaut.2014.12.002">10.1016/j.jaut.2014.12.002</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/PMC4340844">4340844</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/25578468">25578468</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Autoimmunity&rft.atitle=Glycans+in+the+immune+system+and+The+Altered+Glycan+Theory+of+Autoimmunity&rft.volume=57&rft.pages=1-13&rft.date=2015&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4340844%23id-name%3DPMC&rft_id=info%3Apmid%2F25578468&rft_id=info%3Adoi%2F10.1016%2Fj.jaut.2014.12.002&rft.au=Emanual+Maverakis&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4340844&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlycan" class="Z3988"></span></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Glycan&oldid=1227964932">https://en.wikipedia.org/w/index.php?title=Glycan&oldid=1227964932</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Oligosaccharides" title="Category:Oligosaccharides">Oligosaccharides</a></li><li><a href="/wiki/Category:Glycoproteins" title="Category:Glycoproteins">Glycoproteins</a></li><li><a href="/wiki/Category:Carbohydrates" title="Category:Carbohydrates">Carbohydrates</a></li><li><a href="/wiki/Category:Carbohydrate_chemistry" title="Category:Carbohydrate chemistry">Carbohydrate chemistry</a></li><li><a href="/wiki/Category:Glycomics" title="Category:Glycomics">Glycomics</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Articles_needing_additional_references_from_May_2012" title="Category:Articles needing additional references from May 2012">Articles needing additional references from May 2012</a></li><li><a href="/wiki/Category:All_articles_needing_additional_references" title="Category:All articles needing additional references">All articles needing additional references</a></li><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 8 June 2024, at 19:09<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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