Fucose

L-Fucose
IUPAC name (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 Y
PubChem	17106
ChemSpider	16190 Y
UNII	28RYY2IV3F Y
ChEBI	CHEBI:2181 Y
ChEMBL	CHEMBL469449 Y
Jmol-3D images	Image 1
SMILES O[C@@H]1[C@H](O)[C@@H](OC(O)[C@H]1O)C
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 Y Key: SHZGCJCMOBCMKK-DHVFOXMCSA-N Y 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
Properties
Molecular formula	C6H12O5
Molar mass	164.16
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. Alpha1→3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.

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) 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. In human N-linked glycans, fucose is most commonly linked α-1,6 to the reducing terminal beta-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 metabolized by an enzyme called alpha-fucosidase.

L-Fucose is claimed to have application in cosmetics, pharmaceuticals, and dietary supplements.

See also

• Fucitol
• Fuculose
• Fucoidan