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G4401

Sigma-Aldrich

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

≥85%

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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Nicole M Okeley et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(14), 5404-5409 (2013-03-16)
The key role played by fucose in glycoprotein and cellular function has prompted significant research toward identifying recombinant and biochemical strategies for blocking its incorporation into proteins and membrane structures. Technologies surrounding engineered cell lines have evolved for the inhibition
Erandi Lira-Navarrete et al.
PloS one, 6(9), e25365-e25365 (2011-10-04)
Protein O-fucosylation is an essential post-translational modification, involved in the folding of target proteins and in the role of these target proteins during embryonic development and adult tissue homeostasis, among other things. Two different enzymes are responsible for this modification
Qiong Wang et al.
Biotechnology and bioengineering, 115(6), 1378-1393 (2018-02-20)
As a key parameter impacting functional and structural heterogeneity, protein glycosylation is a critical quality attribute for antibody biotherapeutic manufacturing. The glycan patterns on recombinant antibodies, particularly on the conserved fragment crystallizable (Fc) region, can have significant effects on an
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The presence of multiple functional groups and stereocenters in complex carbohydrates makes them challenging targets for the organic chemist.

Glycosyltransferases

Glycosyltransferases were initially considered to be specific for a single glycosyl donor and acceptor, which led to the one enzyme-one linkage concept. Subsequent observations have refuted the theory of absolute enzymatic specificity by describing the transfer of analogs of some nucleoside mono- or diphosphate sugar donors.

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