U4375

Uridine 5′-diphospho-N-acetylglucosamine sodium salt

Name: Uridine 5′-diphospho-N-acetylglucosamine sodium salt
Brand: SIGMA

≥98%, from bakers yeast, powder

Synonym(s):

UDP-GlcNAc, UDP-N-acetylglucosamine, UDPAG

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About This Item

Linear Formula:

C₁₇H₂₅N₃O₁₇P₂Na₂

CAS Number:

91183-98-1

Molecular Weight:

651.32

NACRES:

NA.51

PubChem Substance ID:

24900646

UNSPSC Code:

41106305

EC Number:

293-820-5

MDL number:

MFCD00799985

Product Name

Uridine 5′-diphospho-N-acetylglucosamine sodium salt, ≥98%

InChI key

HXWKMJZFIJNGES-YZVFIFBQSA-L

InChI

1S/C17H27N3O17P2.2Na/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28;;/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28);;/q;2*+1/p-2/t7-,8-,10-,11-,12-,13-,14-,15-,16-;;/m1../s1

SMILES string

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

biological source

bakers yeast

assay

≥98%

form

powder

solubility

water: 50 mg/mL, clear to hazy, colorless

storage temp.

−20°C

Quality Level

200

Related Categories

Biochemicals

Chemistry & Biochemicals

Nucleosides and Nucleotides

Application

Uridine 5′-diphospho-N-acetylglucosamine (UDP-GlcNAc) sodium salt has been used:

as a component of reaction cocktail in endoplasmic reticulum to Golgi transport assay
as a reference standard for the quantification of UDP-GlcNAc in liver tissues using high-performance liquid chromatography (HPLC)
in testing the glycosylation activity of O-GlcNAc transferase (OGT) against peptide substrate

Biochem/physiol Actions

Donor substrate for transfer of GlcNAc to the dolichol precursor in the synthesis of N-glycans. UDP-GlcNAc also functions as the source of GlcNAc attached to serine/threonine residues by O-GlcNAc transferase (OGT) in O-GlcNAc signaling.

Uridine 5′-diphospho-N-acetylglucosamine (UDP-GlcNAc) is a sugar donor and aids in the endomembrane glycosylation of endoplasmic reticulum and Golgi. The decreased levels of UDP-GlcNAc has an influence on the normal cellular proliferation and apoptosis. UDP-GlcNAc elicits feedback inhibition of the enzyme glutamine:fructose-6-phosphate amidotransferase (GFAT).

General description

Uridine 5′-diphospho-N-acetylglucosamine (UDP-GlcNAc) is a nucleotide sugar. It is synthesized from glucose via the hexosamine biosynthetic pathway (HBP). UDP-GlcNAc is transported actively into Golgi, nucleotide sugar transporter (NST). The levels of UDP-GlcNAc is modulated by the concentration of nutrients exposed to the cell.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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A Golgi UDP-GlcNAc transporter delivers substrates for N-linked glycans and sphingolipids

Ebert B, et al.

Nature plants, 1-1 (2018)

Microsome-Based Assay for Analysis of Endoplasmic Reticulum to Golgi Transport in Mammalian Cells

Cell Biology, 209-214 (2006)

CdsA is involved in biosynthesis of glycolipid MPIase essential for membrane protein integration in vivo.

Katsuhiro Sawasato et al.

Scientific reports, 9(1), 1372-1372 (2019-02-06)

MPIase is a glycolipid that is involved in membrane protein integration. Despite evaluation of its functions in vitro, the lack of information on MPIase biosynthesis hampered verification of its involvement in vivo. In this study, we found that depletion of

Peptide microarray analysis of the cross-talk between O-GlcNAcylation and tyrosine phosphorylation.

Jie Shi et al.

FEBS letters, 591(13), 1872-1883 (2017-06-06)

O-GlcNAcylation of proteins regulates important cellular processes. A few reports noted that O-GlcNAcylation exhibits cross-talk with tyrosine phosphorylation. With an activity-based microarray analysis of 256 tyrosine kinase peptide substrates, we found that phosphorylation of six peptides by Jak2 inhibits their

Enhanced transfer of a photocross-linking N-acetylglucosamine (GlcNAc) analog by an O-GlcNAc transferase mutant with converted substrate specificity

Rodriguez AC, et al.

The Journal of biological chemistry, 290(37), 22638-22648 (2015)

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