Name: Uridine 5′-diphosphoglucose disodium salt
Brand: SIGMA

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₂N₂Na₂O₁₇P₂

CAS Number:

28053-08-9

Molecular Weight:

610.27

Beilstein/REAXYS Number:

4290380

EC Number:

248-801-6

MDL number:

MFCD00216890

UNSPSC Code:

41106305

PubChem Substance ID:

329770327

NACRES:

NA.51

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biological source

Saccharomyces cerevisiae

assay

≥98.0% (HPLC)

form

powder

impurities

≤5% solvent
≤8.5% water

solubility

H₂O: 50 mg/mL, clear

storage temp.

−20°C

SMILES string

[Na+].[Na+].OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C15H24N2O17P2.2Na/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25;;/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25);;/q;2*+1/p-2/t5-,6-,8-,9-,10+,11-,12-,13-,14-;;/m1../s1

InChI key

PKJQEQVCYGYYMM-QBNUFUENSA-L

General description

Uridine5′-diphosphoglucose disodium salt is a nucleotide sugar consisting of a uracil base, ribose sugar, and two phosphate groups.

Application

UDP-glucose has been used:

as a substrate in the enzymatic production of glycosides and their detection by liquid chromatography-mass spectrometry.
as a substrate in the substrate screening and binding affinity measurements of the human CMP-Sia transporter.

Biochem/physiol Actions

UDP-glucose, acts as a precursor of UDP-galactose and UDP-glucuronate. In addition, it also aids in the biosynthesis of glucose-containing molecules such as oligosaccharides, polysaccharides, glycoproteins, and glycolipids in animals and some microorganisms . Several studies suggest that UDP-Glucose has the potential to act as a signaling molecule in plants beyond its classical metabolic functions . Uridine-5′-diphosphoglucose acts as an agonist to the purinergic receptor P2Y14 G protein-coupled receptor (GPCR) receptor, involved in the activation of dendritic cells and glial cells. It can also activate G protein-coupled receptor 17 (GPR17) thereby inducing oligodendrocyte differentiation.

Other Notes

Stimulates the reduction of methylcoenzyme M in cell-free extracts of Methanobacterium thermoautotrophicum

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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