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G4401

Sigma-Aldrich

Guanosine 5′-diphospho-β-L-fucose sodium salt

≥85%, powder

Synonym(s):

6-Deoxy-β-L-galactopyranosylguanosine 5′-diphosphate, GDP-Fuc, GDP-fucose

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About This Item

Empirical Formula (Hill Notation):
C16H23N5Na2O15P2
CAS Number:
15839-70-0
Molecular Weight:
633.31
MDL number:
MFCD00058553
UNSPSC Code:
12352204
PubChem Substance ID:
24895171
NACRES:
NA.32

product name

Guanosine 5′-diphospho-β-L-fucose sodium salt, ≥85%

assay

≥85%

form

powder

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

CC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)n3cnc4C(=O)N=C(N)Nc34)C(O)C(O)C1O

InChI

1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)

InChI key

LQEBEXMHBLQMDB-UHFFFAOYSA-N

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General description

Guanosine 5′-diphospho-β-L-fucose (GDP-fucose) is a sugar nucleotide present in bacteria and humans and is a fucosyltransferase substrate.

Application

Guanosine 5′-diphospho-β-L-fucose sodium salt may be used as a component of fucosyltransferase VII (FTVII) reaction buffer to aid exofucosylation in murine adipose tissue-derived mesenchymal stromal cells (AMSCs). It has been used for microbe agglutination assay and agglutination inhibition assay.
Guanosine 5′-diphospho-β-L-fucose sodium salt has been used for microbe agglutination assay and agglutination inhibition assay.

Substrates

Substrate for fucosyltransferase

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Stephen T B Lau et al.
Journal of the American Chemical Society, 130(51), 17593-17602 (2008-12-05)
L-fucose, 6-deoxy-L-galactose, is a key component of many important glycoconjugates including the blood group antigens and the Lewis(X) ligands. The biosynthesis of GDP-L-fucose begins with the action of a dehydratase that converts GDP-D-mannose into GDP-4-keto-6-deoxy-mannose. The enzyme GDP-fucose synthase, GFS
Qiang Yang et al.
The Journal of biological chemistry, 292(36), 14796-14803 (2017-07-22)
The mammalian α1,6-fucosyltransferase (FUT8) catalyzes the core fucosylation of
Laure Barbé et al.
Scientific reports, 8(1), 12961-12961 (2018-08-30)
Human strains of rotavirus A (RVAs) recognize fucosylated glycans belonging to histo-blood group antigens (HBGAs) through their spike protein VP8*. Lack of these ligands due to genetic polymorphisms is associated with resistance to gastroenteritis caused by P[8] genotype RVAs. With
Wei Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(38), 16096-16101 (2009-10-07)
Lewis X (Le(x))-containing glycans play important roles in numerous cellular processes. However, the absence of robust, facile, and cost-effective methods for the synthesis of Le(x) and its structurally related analogs has severely hampered the elucidation of the specific functions of
Diego Sánchez-Martínez et al.
Clinical and translational medicine, 11(2), e280-e280 (2021-02-27)
CD19-directed chimeric antigen receptors (CAR) T cells induce impressive rates of complete response in advanced B-cell malignancies, specially in B-cell acute lymphoblastic leukemia (B-ALL). However, CAR T-cell-treated patients eventually progress due to poor CAR T-cell persistence and/or disease relapse. The
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