Fucose

L-Fucose

Names
IUPAC names (3S,4R,5S,6S)-6-Methyltetrahydro- 2H-pyran-2,3,4,5-tetraol
Other names 6-Deoxy-L-galactose
Identifiers
CAS Number	2438-80-4
ChEBI	CHEBI:2181
ChEMBL	ChEMBL469449
ChemSpider	16190
Jmol interactive 3D	Image
PubChem	17106
UNII	28RYY2IV3F
InChI InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1 Key: SHZGCJCMOBCMKK-DHVFOXMCSA-N 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 Key: SHZGCJCMOBCMKK-DHVFOXMCBB
SMILES O[C@@H]1[C@H](O)[C@@H](OC(O)[C@H]1O)C
Properties
Chemical formula	C6H12O5
Molar mass	164.16
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
verify (what is  ?)
Infobox references

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, and is the fundamental sub-unit of the fucoidan polysaccharide. α(1→3) linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.^[1]

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-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.^[2] 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.

L-Fucose is claimed to have application in cosmetics, pharmaceuticals, and dietary supplements. However, these claims are often not supported by peer-reviewed scientific studies.

Fucosylation of antibodies has been established to reduce binding to the Fc receptor (FcgammaRIIIA) of Natural Killer cells and thereby reduce antigen-dependent cellular cytotoxicity. Therefore therapeutic antibodies that are designed to recruit the immune system to cancers cells ave been manufactured in cell lines deficient in the enzyme for core fucosylation (FUT8) and thereby enhancing the in vivo cell killing.^[3]

See also

• Fucitol
• Verotoxin-producing Escherichia coli
• Digitalose, the methyl ether of D-fucose

References

1. Daniel J. Becker; John B. Lowe (July 2003). "Fucose: biosynthesis and biological function in mammals". Glycobiology 13 (7): 41R–53R. doi:10.1093/glycob/cwg054. PMID 12651883.
2. Daniel J. Moloney; Robert S. Haltiwanger (July 1999). "The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose-[beta]1,3-glucosyltransferase activity from Chinese hamster ovary cells". Glycobiology 9 (7): 679–687. doi:10.1093/glycob/9.7.679. PMID 10362837. delete character in |title= at position 118 (help)
3. Dalziel, Martin; Crispin, Max; Scanlan, Christopher N.; Zitzmann, Nicole; Dwek, Raymond A. (2014-01-03). "Emerging Principles for the Therapeutic Exploitation of Glycosylation". Science 343 (6166): 1235681. doi:10.1126/science.1235681. ISSN 0036-8075. PMID 24385630.