| Revision as of 14:33, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,137 edits Saving copy of the {{chembox}} taken from revid 453595608 of page Fucose for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 23:00, 22 November 2024 edit 2601:643:8581:2490:6f72:76b3:dbd8:afed (talk)No edit summaryTags: Mobile edit Mobile web edit |
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{{distinguish|Fructose}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 450941131 |
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| verifiedrevid = 461114230 |
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| Name = <small>L</small>-Fucose |
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| Name = {{Sma|L}}-Fucose |
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| ImageFile = L-Fucose_pyranose_chemical_structure.png |
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| ImageFile = L-Fucose.png |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| ImageFile2 = L-Fucose_chemical_structure.png |
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| ImageFile2 = L-Fucose_chemical_structure.png |
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| ImageSize2 = 140px |
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| ImageSize2 = 140px |
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| IUPACName = (3''S'',4''R'',5''S'',6''S'')-6-Methyltetrahydro-<br>2''H''-pyran-2,3,4,5-tetraol |
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| OtherNames = 6-Deoxy-<small>L</small>-galactose |
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| IUPACName = 6-Deoxy-<small>L</small>-galactopyranose |
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| OtherNames = 6-Deoxy-{{Sma|L}}-galactose |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = (2''S'',3''R'',4''R'',5''S'')-6-Methyltetrahydro-<wbr>2''H''-pyran-2,3,4,5-tetraol |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 16190 |
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| ChemSpiderID = 16190 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 2438-80-4 |
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| CASNo = 2438-80-4 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 469449 |
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| ChEMBL = 469449 |
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| PubChem = 17106 |
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| PubChem = 17106 |
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| SMILES = O1(O)(OC(O)1O)C |
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| SMILES = O1(O)(OC(O)1O)C |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>5</sub> |
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| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>5</sub> |
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| MolarMass = 164.16 |
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| MolarMass = 164.16 g/mol |
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'''Fucose''' is a ] ] with the ] C<sub>6</sub>H<sub>12</sub>O<sub>5</sub>. It is found on ]s on the ]ian, ] and ] ] Fucose is the fundamental sub-unit of the ] ] ].<ref>{{Cite journal|date=2017-09-01|title=Polysaccharides from macroalgae: Recent advances, innovative technologies and challenges in extraction and purification|journal=Food Research International|language=en|volume=99|issue=Pt 3|pages=1011–1020|doi=10.1016/j.foodres.2016.11.016|pmid=28865611|issn=0963-9969|last1=Garcia-Vaquero|first1=M.|last2=Rajauria|first2=G.|last3=O'Doherty|first3=J.V.|last4=Sweeney|first4=T.|hdl=10197/8191|s2cid=10531419 |hdl-access=free}}</ref> The ] core of fucoidan is a suspected ] ] for ]-mediated ].<ref>] {{cite journal| title=Fucose: biosynthesis and biological function in mammals|date=July 2003| pmid=12651883| author=Daniel J. Becker|author2=John B. Lowe| journal=Glycobiology| volume=13| pages=41R–53R| doi=10.1093/glycob/cwg054| issue=7| doi-access=free}}</ref> |
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Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a ] group on the carbon at the 6-position (C-6) (thereby making it a ]) and the <small>]</small>]. It is equivalent to 6-deoxy-{{Sma|L}}-]. |
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In the fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars.<ref>] {{cite journal| title=The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-<nowiki></nowiki>1,3-glucosyltransferase activity from Chinese hamster ovary cells|date=July 1999| pmid=10362837| author=Daniel J. Moloney|author2=Robert S. Haltiwanger| journal=Glycobiology| volume=9| pages=679–687| doi=10.1093/glycob/9.7.679| issue=7|author2-link=Robert S. Haltiwanger| doi-access=free}}</ref> |
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In human ''N''-linked glycans, fucose is most commonly linked α-1,6 to the reducing terminal ]. However, fucose at the non-reducing termini linked α-1,2 to galactose forms the ], the substructure of the A and B blood group antigens. |
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Fucose is released from fucose-containing polymers by an enzyme called ] found in ]s. |
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<small>L</small>-Fucose has several potential applications in cosmetics, pharmaceuticals, and dietary supplements<ref>{{cite journal |last1=Roca |first1=C |title=Exopolysaccharides enriched in rare sugars: bacterial sources, production, and applications |journal=Front Microbiol |date=2015 |volume=6 |page=288 |pmid=25914689|pmc=4392319 |doi=10.3389/fmicb.2015.00288 |doi-access=free }}</ref><ref>{{cite journal |last1=Vanhooren |first1=PT |title=L-fucose: occurrence, physiological role, chemical, enzymatic and microbial synthesis |journal=J. Chem. Technol. Biotechnol. |date=1999 |volume=74 |issue=6 |pages=479–497|doi=10.1002/(SICI)1097-4660(199906)74:6<479::AID-JCTB76>3.0.CO;2-E }}</ref> |
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] of antibodies has been established to reduce binding to the ] of ] cells and thereby reduce ]. Therefore, ] have been designed to recruit the immune system to cancers cells have been manufactured in cell lines deficient in the enzyme for core fucosylation (]), thereby enhancing the in vivo cell killing.<ref>{{Cite journal|last1=Dalziel|first1=Martin|last2=Crispin|first2=Max|last3=Scanlan|first3=Christopher N.|last4=Zitzmann|first4=Nicole|last5=Dwek|first5=Raymond A.|date=2014-01-03|title=Emerging Principles for the Therapeutic Exploitation of Glycosylation |journal=Science|language=en|volume=343|issue=6166|pages=1235681|doi=10.1126/science.1235681|issn=0036-8075|pmid=24385630|s2cid=206548002}}</ref><ref name=Yu2017>{{cite journal|last1=Yu|first1=X|last2=Marshall|first2=MJE|last3=Cragg|first3=MS|last4=Crispin|first4=M|title=Improving Antibody-Based Cancer Therapeutics Through Glycan Engineering.|journal=BioDrugs|date=June 2017|volume=31|issue=3|pages=151–166|doi=10.1007/s40259-017-0223-8|pmid=28466278|s2cid=3722081|url=https://eprints.soton.ac.uk/410615/1/Resubmission_Yu_Manuscript_and_table.pdf}}<!--https://eprints.soton.ac.uk/410615/1/Resubmission_Yu_Manuscript_and_table.pdf--></ref> |
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== See also == |
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* ], the methyl ether of <small>D</small>-fucose |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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{{Carbohydrates}} |
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] |
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] |
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] |