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Merck

94335

Uridine 5′-diphosphoglucose disodium salt

≥98.0% (HPLC), from Saccharomyces cerevisiae, powder

Synonyme(s) :

UDP-D-Glucose disodium salt, UDPG, UDP-glc, Uridine-diphosphate-glucose disodium salt, Uridine[5’]diphospho[1]-α-D-glucopyranose disodium salt

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A propos de cet article

Formule empirique (notation de Hill) :
C15H22N2Na2O17P2
Numéro CAS:
28053-08-9
Poids moléculaire :
610.27
NACRES:
NA.51
PubChem Substance ID:
329770327
UNSPSC Code:
41106305
EC Number:
248-801-6
MDL number:
MFCD00216890
Beilstein/REAXYS Number:
4290380

Principaux documents

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Nom du produit

Uridine 5′-diphosphoglucose disodium salt, ≥98.0% (HPLC)

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

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

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

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.

General description

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

Other Notes

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
BCCN4359
BCCN4358
BCCN1190
BCCM6600
BCCM6602

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Consulter la Bibliothèque de documents

Alexander Gutmann et al.
Organic & biomolecular chemistry, 15(37), 7917-7924 (2017-09-14)
Various bioactive natural products, like the aminocoumarin antibiotics novobiocin and coumermycin, exhibit an aromatic C-methyl group adjacent to a glycosylated phenolic hydroxyl group. Therefore, tailoring of basic phenolic scaffolds to contain the intricate C-methyl/O-glycosyl motif is of high interest for
Sen Yin et al.
Plant physiology and biochemistry : PPB, 109, 536-548 (2016-11-12)
UDP-L-rhamnose (UDP-Rha) is an important sugar donor for the synthesis of rhamnose-containing compounds in plants. However, only a few enzymes and their encoding genes involved in UDP-Rha biosynthesis are available in plants. Here, two genes encoding rhamnose synthase (RhS) and
Ayako Ikegami et al.
Planta, 230(4), 841-855 (2009-07-31)
Fruits of persimmon (Diospyros kaki Thunb.) accumulate large amounts of proanthocyanidins (PAs) in the early stages of development. Astringent (A)-type fruits remain rich in soluble PAs even after they reach full-mature stage, whereas non-astringent (NA)-type fruits lose these compounds before
Nan Li et al.
Carbohydrate research, 446-447, 61-67 (2017-05-22)
Corylifol A, a member of the isoflavone subclass of isoflavonoids, has long been considered to have various biological activities. Here, we sought to synthesize corylifol A glucosides by the in vitro glucosylation reaction using the UDP-glycosyltransferase YjiC from Bacillus licheniformis DSM
Jo M Vanoevelen et al.
Journal of inherited metabolic disease, 41(1), 117-127 (2017-09-16)
Classic galactosemia is a genetic disorder of galactose metabolism, caused by severe deficiency of galactose-1-phosphate uridylyltransferase (GALT) enzyme activity due to mutations of the GALT gene. Its pathogenesis is still not fully elucidated, and a therapy that prevents chronic impairments
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