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Fucose
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IUPAC names
(3S,4R,5S,6S)-6-Methyltetrahydro-
2H-pyran-2,3,4,5-tetraol | |
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Other names
6-Deoxy-L-galactose
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2438-80-4 7px | |
ChEBI | CHEBI:2181 7px | |
ChEMBL | ChEMBL469449 7px | |
ChemSpider | 16190 7px | |
Jmol-3D images | Image | |
PubChem | Template:Chembox PubChem/format | |
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C6H12O5 | |
Molar mass | 164.16 | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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. 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.
Anti-carcinogenic properties
The mushroom species Ganoderma lucidum AKA Reishi mushrooms contains alkaloid L-fucose, which has been found in polysaccharide and carbohydrate-based vaccine studies to have anti-tumor activity in mice with Lewis lung carcinoma cells. [3] 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.
See also
- Fucitol
- Verotoxin-producing Escherichia coli
- Digitalose, the methyl ether of D-fucose
References
- ^ File:Free review.png Daniel J. Becker; John B. Lowe (July 2003). "Fucose: biosynthesis and biological function in mammals". Glycobiology 13 (7): 41R–53R. PMID 12651883. doi:10.1093/glycob/cwg054.
- ^ File:Free text.png 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. PMID 10362837. doi:10.1093/glycob/9.7.679.
- ^ "Immunization of focus-containing polysaccharides from Reishi mushroom induces antibodies to tumor-associated Globo H-series epitopes.". National Institue of Health. 20 August 2013. Retrieved 8 May 2015.
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