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U4375

Sigma-Aldrich

Uridine 5′-diphospho-N-acetylglucosamine sodium salt

≥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
EC Number:
293-820-5
MDL number:
MFCD00799985
UNSPSC Code:
41106305
PubChem Substance ID:
24900646
NACRES:
NA.51

Key Documents

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Product Name

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

biological source

bakers yeast

Quality Level

200

Assay

≥98%

form

powder

solubility

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

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

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000385409
0000379134
0000354136
0000354137
0000354135

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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)
Stephanie M Halmo et al.
The Journal of biological chemistry, 292(6), 2101-2109 (2016-12-10)
Disruption of the
Aksana A Labokha et al.
The EMBO journal, 32(2), 204-218 (2012-12-04)
Nuclear pore complexes (NPCs) control the traffic between cell nucleus and cytoplasm. While facilitating translocation of nuclear transport receptors (NTRs) and NTR·cargo complexes, they suppress passive passage of macromolecules 30 kDa. Previously, we reconstituted the NPC barrier as hydrogels comprising S.
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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