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Merck

94335

Sigma-Aldrich

Uridin-5′-diphosphoglucose Dinatriumsalz

≥98.0% (HPLC)

Synonym(e):

UDP-glc, Uridin-diphosphat-glucose Dinatriumsalz, Uridin[5’]diphospho[1]-α-D-glucopyranose Dinatriumsalz

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About This Item

Empirische Formel (Hill-System):
C15H22N2Na2O17P2
CAS-Nummer:
Molekulargewicht:
610.27
Beilstein:
4290380
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
41106305
PubChem Substanz-ID:
NACRES:
NA.51

Biologische Quelle

Saccharomyces cerevisiae

Assay

≥98.0% (HPLC)

Form

powder

Verunreinigungen

≤5% solvent
≤8.5% water

Löslichkeit

H2O: 50 mg/mL, clear

Lagertemp.

−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

InChIKey

PKJQEQVCYGYYMM-QBNUFUENSA-L

Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Sonstige Hinweise

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

Ersetzt durch

Produkt-Nr.
Beschreibung
Preisangaben

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Plant physiology and biochemistry : PPB, 109, 536-548 (2016-11-12)
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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

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