L-Fucose | |
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(3S,4R,5S,6S)-6-Methyltetrahydro- |
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Other names
6-Deoxy-L-galactose |
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Identifiers | |
CAS number | 2438-80-4 ![]() |
PubChem | 17106 |
ChemSpider | 16190 ![]() |
UNII | 28RYY2IV3F ![]() |
ChEBI | CHEBI:2181 ![]() |
ChEMBL | CHEMBL469449 ![]() |
Jmol-3D images | Image 1 |
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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 |
![]() ![]() ![]() Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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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.[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 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.[3]
See also
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. http://glycob.oxfordjournals.org/cgi/content/full/13/7/41R.
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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. http://glycob.oxfordjournals.org/cgi/content/full/9/7/679.
- ^ Danisco Co. product literature.
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