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L-fucopyranose

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Origin: China

Cas No: 2438-80-4

Specification: 99%min

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    CAS No.: 2438-80-4 Formula: C6H12O5 Molecular Weight: 164.15600

    Description

    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.
    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) (thereby making it a deoxy sugar) 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. 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. However, these claims are often not supported by peer-reviewed scientific studies.
    Fucosylation of antibodies has been established to reduce binding to the Fc receptor (FcgammaRIIIA) of Natural Killer cells and thereby reduce antigen-dependent cellular cytotoxicity. Therefore therapeutic antibodies that are designed to recruit the immune system to cancers cells ave been manufactured in cell lines deficient in the enzyme for core fucosylation (FUT8) and thereby enhancing the in vivo cell killing.

    Basic Info

    Chemical Name L-fucopyranose
    Synonyms

    L-(-)-fucose 6-Deoxy-L-galactoseL-(-)-Rhodeose;
    L-(?)-Fucose;
    L-GalactoMethylose;
    L-(-)-Flucose;
    6-deoxy-l-galactos;
    L-(−)-Fucose;
    6-Deoxy-L-galactose;
    L-(-)-Rhodeose;
    FUCOSE,L;
    6-Desoxygalactose;
    L-(-)-Fucose;
    L-FUCOSE;

    CAS No. 2438-80-4
    Molecular Formula C6H12O5
    Molecular Weight 164.15600
    PSA 97.99000
    LogP -2.35120

    Properties

    Appearance & Physical State White solid
    Density 1.556g/cm3
    Boiling Point 323.9ºC at 760mmHg
    Melting Point 150-153ºC(lit.)
    Flash Point 149.7ºC
    Refractive Index -75.5 ° (C=10, H2O)
    Stability Stable. Incompatible with strong oxidizing agents.
    Storage Condition -20ºC Freezer
    Vapor Pressure 5E-08mmHg at 25°C

    Safety Info

    Safety Statements S24/25
    HS Code 2912491000
    WGK Germany 3

    Synthesis Route

    aldehydo-D-rhamnosealdehydo-D-fucose+L-fucopyranose
    α-L-Fuc-(1--3)-β-D-GalNAc-(1--3)-β-D-Gal-(1--4)-β-D-Gal-(1--3)-D-GalNAc-olD-galactopyranose+L-fucopyranose
    acetic acid+2′-Fucosyl-D-lactoseL-fucopyranose+lactose

    Precursor

    2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide
    β-L-fucopyranosyl azide
    N-(tert-butoxycarbonyl)-L-proline 2-(diphenylphosphanyl)-4-fluorophenyl ester
    6-Deoxy-L-talose

    Downstream Product

    L-Rhamnose Bis(ethylsulfone)
    (6R)-2,6-Anhydro-1-deoxy-6-(nitromethyl)-D-galactitol
    (S)-(+)-6-METHYL-5-HEPTEN-2-OL
    5-Methyl furfural

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