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Fucose

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L-Fucose
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IUPAC names
(3S,4R,5S,6S)-6-Methyltetrahydro-
2H-pyran-2,3,4,5-tetraol
Other names
6-Deoxy-L-galactose
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2438-80-4 7pxY
ChEBI CHEBI:2181 7pxY
ChEMBL ChEMBL469449 7pxY
ChemSpider 16190 7pxY
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C6H12O5
Molar mass 164.16
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Thermodynamic
data

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxY verify (what is10pxY/10pxN?)
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

References