U4375

Uridine 5′-diphospho-N-acetylglucosamine sodium salt

≥98%

• 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

Properties

• biological source: bakers yeast
• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves