Fucose

Fucose

Chembox new
Name = L-Fucose
ImageFile = L-Fucose_pyranose_chemical_structure.png ImageSize = 120px
ImageFile2 = L-Fucose_chemical_structure.png ImageSize2 = 140px
IUPACName = (3S,4R,5S,6S)-6-Methyltetrahydro-
2"H"-pyran-2,3,4,5-tetraol
OtherNames = 6-Deoxy-L-galactose
Section1 = Chembox Identifiers
CASNo = 2438-80-4
PubChem = 17106
SMILES =

Section2 = Chembox Properties
Formula = C6H12O5
MolarMass = 164.16

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. [ cite journal| title=Fucose: biosynthesis and biological function in mammals| year=2003| month=July| pmid=12651883| url=http://glycob.oxfordjournals.org/cgi/content/full/13/7/41R| author=Daniel J. Becker| coauthors=John B. Lowe| journal=Glycobiology| volume=13| pages=41R–53R| doi=10.1093/glycob/cwg054]

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. [ cite journal| title=The O-linked fucose glycosylation pathway: identification and characterization of a uridine diphosphoglucose: fucose- [beta] 1,3-glucosyltransferase activity from Chinese hamster ovary cells| year=1999| month=July| pmid=10362837| url=http://glycob.oxfordjournals.org/cgi/content/full/9/7/679| author=Daniel J. Moloney| coauthors=Robert S. Haltiwanger| journal=Glycobiology| volume=9| pages=679–687| doi=10.1093/glycob/9.7.679] In human "N"-linked glycans, fucose is most commonly linked alpha 1,6 to the reducing terminal beta-"N"-acetlyglucosamine. However, fucose at the non-reducing termini linked alpha 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.

See also

* Fucitol
* Fuculose
* Fucoidan

References


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