Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Fucose: Difference between pages

{{distinguish|Fructose}}

| Watchedfields = changed

| verifiedrevid = 461114230

| Name = {{sm|l}}-Fucose

| ImageFile = L-Fucose.png

| ImageSize = 120px

| ImageFile2 = L-Fucose_chemical_structure.png

| ImageSize2 = 140px

| IUPACName = 6-Deoxy-<small>L</small>-galactopyranose

| OtherNames = 6-Deoxy-{{sm|l}}-galactose

| SystematicName = (2''S'',3''R'',4''R'',5''S'')-6-Methyltetrahydro-<wbr>2''H''-pyran-2,3,4,5-tetraol

| Section1 = {{Chembox Identifiers

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| Section2 = {{Chembox Properties

| MolarMass = 164.16 g/mol

'''Fucose''' is a [[hexose]] [[deoxy sugar]] with the [[chemical formula]] C₆H₁₂O₅. It is found on [[N-linked glycan|''N''-linked glycan]]s on the [[mammal]]ian, [[insect]] and [[plant]] [[Cell membrane|cell surface.]] Fucose is the fundamental sub-unit of the [[seaweed]] [[polysaccharide]] [[fucoidan]].<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 [[Anomer|α(1→3) linked]] core of fucoidan is a suspected [[carbohydrate]] [[antigen]] for [[Immunoglobulin E|IgE]]-mediated [[allergy]].<ref>[[Image:Free review.png]] {{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>

Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a [[hydroxyl]] group on the carbon at the 6-position (C-6) (thereby making it a [[deoxy sugar]]) and the <small>[[Dextrorotation and levorotation|L]]</small>[[Dextrorotation and levorotation|-configuration]]. It is equivalent to 6-deoxy-{{sm|l}}-[[galactose]].

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>[[Image:Free text.png]] {{cite journal| title=The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-<nowiki>[beta]</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>

In human ''N''-linked glycans, fucose is most commonly linked α-1,6 to the reducing terminal β-''N''-acetylglucosamine. However, fucose at the non-reducing termini linked α-1,2 to galactose forms the [[ABO blood group system#Antigens|H antigen]], the substructure of the A and B blood group antigens.

Fucose is released from fucose-containing polymers by an enzyme called α-[[fucosidase]] found in [[lysosome]]s.

{{sm|l}}-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>

[[Fucosylation]] of antibodies has been established to reduce binding to the [[Fc receptor]] of [[Natural killer cell|Natural Killer]] cells and thereby reduce [[Antibody-dependent cellular cytotoxicity|antigen-dependent cellular cytotoxicity]]. Therefore, [[afucosylated monoclonal antibodies]] have been designed to recruit the immune system to cancers cells have been manufactured in cell lines deficient in the enzyme for core fucosylation ([[FUT8]]), 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>

== See also ==

* [[Digitalose]], the methyl ether of <small>D</small>-fucose

* [[Fucitol]]

* [[Verotoxin-producing Escherichia coli|Verotoxin-producing ''Escherichia coli'']]

==References==

{{Reflist}}

{{Carbohydrates}}

[[Category:Aldohexoses]]

[[Category:Deoxy sugars]]

[[Category:Pyranoses]]