Fucose
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| Names | |
|---|---|
| IUPAC names
(3S,4R,5S,6S)-6-Methyltetrahydro- 2H-pyran-2,3,4,5-tetraol | |
| Other names
6-Deoxy-L-galactose | |
| Identifiers | |
2438-80-4  | |
| ChEBI | CHEBI:2181 |
| ChEMBL | ChEMBL469449 |
| ChemSpider | 16190 |
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| Jmol-3D images | Image |
| PubChem | 17106 |
| |
| UNII | 28RYY2IV3F |
| Properties | |
| C6H12O5 | |
| Molar mass | 164.16 |
| Supplementary data page | |
| Refractive index (n), Dielectric constant (εr), etc. | |
| Thermodynamic data |
Phase behaviour solid–liquid–gas |
| UV, IR, NMR, MS | |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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) 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.[3]
See also
- Fucitol
- Verotoxin-producing Escherichia coli
- Digitalose, the methyl ether of D-fucose
References
- ↑
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. - ↑
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. - ↑ Danisco Co. product literature.
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