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07508

Sigma-Aldrich

Guanosine 5′-diphospho-α-D-mannose disodium salt

≥95.0% (HPLC)

Synonym(s):

GDP-D-mannose disodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H23N5Na2O16P2
CAS Number:
148296-46-2
Molecular Weight:
649.30
MDL number:
MFCD00799981
UNSPSC Code:
12352204
PubChem Substance ID:
329748460
NACRES:
NA.32

Assay

≥95.0% (HPLC)

form

powder or crystals

storage temp.

−20°C

SMILES string

[Na+].[Na+].NC1=Nc2c(ncn2[C@@H]3O[C@H](COP([O-])(=O)OP([O-])(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H]3O)C(=O)N1

InChI

1S/C16H25N5O16P2.2Na/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15;;/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28);;/q;2*+1/p-2/t4-,5-,7-,8-,9+,10-,11+,14-,15-;;/m1../s1

InChI key

XOAGKSFNHBWACO-RAUZPKMFSA-L

Biochem/physiol Actions

Intermediate in fructose and mannose metabolism, ascorbate and aldarate metabolism, amino sugar and nucleotide sugar metabolism and N-Glycan biosynthesis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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P L Conklin et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(7), 4198-4203 (1999-03-31)
Vitamin C (L-ascorbic acid; AsA) acts as a potent antioxidant and cellular reductant in plants and animals. AsA has long been known to have many critical physiological roles in plants, yet its biosynthesis is only currently being defined. A pathway
M Tonetti et al.
Biochimie, 80(11), 923-931 (1999-01-20)
L-fucose and L-rhamnose are two 6-deoxyhexoses naturally occurring in several complex carbohydrates. In prokaryotes both of them are found in polysaccharides of the cell wall, while in animals only L-fucose has been described, which mainly participates to the structure of
Sabine Kuettel et al.
Molecular microbiology, 84(2), 340-351 (2012-03-02)
The sugar nucleotide GDP-mannose is essential for Trypanosoma brucei. Phosphomannose isomerase occupies a key position on the de novo pathway to GDP-mannose from glucose, just before intersection with the salvage pathway from free mannose. We identified the parasite phosphomannose isomerase
Beata A Wolucka et al.
The Journal of biological chemistry, 278(48), 47483-47490 (2003-09-05)
Despite its importance for agriculture, bioindustry, and nutrition, the fundamental process of L-ascorbic acid (vitamin C) biosynthesis in plants is not completely elucidated, and little is known about its regulation. The recently identified GDP-Man 3',5'-epimerase catalyzes a reversible epimerization of
N Smirnoff
Vitamins and hormones, 61, 241-266 (2001-01-12)
Biosynthesis of L-ascorbate (vitamin C) occurs by different pathways in plants and mammals. Yeast contain D-erythroascorbate, a C5 analog of ascorbate. UDP-D-glucuronic acid is the precursor in mammals. Loss of UDP forms glucuronic acid/glucuronolactone. Reduction of these at C-1 then

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