fucose

{{distinguish|Fructose}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 461114230

| Name = {{Sma|L}}-Fucose

| ImageFile = L-Fucose.png

| ImageSize = 120px

| ImageFile2 = L-Fucose_chemical_structure.png

| ImageSize2 = 140px

| IUPACName = 6-Deoxy-L-galactopyranose

| OtherNames = 6-Deoxy-{{Sma|L}}-galactose

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

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16190

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 28RYY2IV3F

| InChI = 1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1

| InChIKey = SHZGCJCMOBCMKK-DHVFOXMCBB

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SHZGCJCMOBCMKK-DHVFOXMCSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 2438-80-4

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

| ChEMBL = 469449

| PubChem = 17106

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 2181

| SMILES = O[C@@H]1[C@H](O)[C@@H](OC(O)[C@H]1O)C

}}

| Section2 = {{Chembox Properties

| Formula = C₆H₁₂O₅

| MolarMass = 164.16 g/mol

}}

}}

Fucose is a hexose deoxy sugar with the chemical formula C₆H₁₂O₅. It is found on N-linked glycans on the mammalian, insect and plant cell surface. Fucose is the fundamental sub-unit of the seaweed polysaccharide fucoidan.{{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}} The α(1→3) linked core of fucoidan is a suspected carbohydrate antigen for IgE-mediated allergy.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}}

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 L-configuration. It is equivalent to 6-deoxy-{{Sma|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.Image:Free text.png {{cite journal| title=The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-[beta]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}}

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 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 lysosomes.

L-Fucose has several potential applications in cosmetics, pharmaceuticals, and dietary supplements{{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 }}{{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 }}

Fucosylation of antibodies has been established to reduce binding to the Fc receptor of Natural Killer cells and thereby reduce antibody-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.{{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}}{{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}}