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U4375

Sigma-Aldrich

Uridine 5′-diphospho-N-acetylglucosamine sodium salt

≥98%

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Synonym(s):
UDP-GlcNAc, UDP-N-acetylglucosamine, UDPAG
Linear Formula:
C17H25N3O17P2Na2
CAS Number:
91183-98-1
Molecular Weight:
651.32
EC Number:
293-820-5
MDL number:
MFCD00799985
UNSPSC Code:
41106305
PubChem Substance ID:
24900646
NACRES:
NA.51

biological source

bakers yeast

Quality Level

200

Assay

≥98%

form

powder

storage temp.

−20°C

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

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

InChI key

HXWKMJZFIJNGES-YZVFIFBQSA-L

Related Categories

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.

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

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).
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Microsome-Based Assay for Analysis of Endoplasmic Reticulum to Golgi Transport in Mammalian Cells
Cell Biology, 209-214 (2006)
Thanuja Gangi Setty et al.
ACS omega, 5(48), 30923-30936 (2020-12-17)
Several pathogenic bacteria import and catabolize sialic acids as a source of carbon and nitrogen. Within the sialic acid catabolic pathway, the enzyme N-acetylmannosamine kinase (NanK) catalyzes the phosphorylation of N-acetylmannosamine to N-acetylmannosamine-6-phosphate. This kinase belongs to the ROK superfamily
A Golgi UDP-GlcNAc transporter delivers substrates for N-linked glycans and sphingolipids
Ebert B, et al.
Nature plants, 1-1 (2018)
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
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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