N9376

4-Nitrophenyl N-acetyl-β-D-glucosaminide

chromogenic, ≥99% (TLC), powder

• Synonym(s): 4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• Empirical Formula (Hill Notation): C₁₄H₁₈N₂O₈
• CAS Number: 3459-18-5
• Molecular Weight: 342.30
• Beilstein/REAXYS Number: 96193
• EC Number: 222-398-7
• MDL number: MFCD00063696
• UNSPSC Code: 12352204
• PubChem Substance ID: 24897896
• NACRES: NA.32

Properties

• product name: 4-Nitrophenyl N-acetyl-β-D-glucosaminide, ≥99% (TLC)
• assay: ≥99% (TLC)
• form: powder
• impurities: ≤0.05% Free p-nitrophenol
• solubility: water: 5 mg/mL, clear, colorless to very faintly yellow
• storage temp.: −20°C
• SMILES string: CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1Oc2ccc(cc2)[N+]([O-])=O
• InChI: 1S/C14H18N2O8/c1-7(18)15-11-13(20)12(19)10(6-17)24-14(11)23-9-4-2-8(3-5-9)16(21)22/h2-5,10-14,17,19-20H,6H2,1H3,(H,15,18)/t10-,11-,12-,13-,14-/m1/s1
• InChI key: OMRLTNCLYHKQCK-DHGKCCLASA-N

Description

Application

N-acetyl-β-D-glucosaminidase (NAG) has been used:

• as a substrate to assay N-acetyl-β-D-glucosaminidase (NAG)
• as a substrate to study chitinase ChiB1 activity
• to assess degranulation using rat basophilic leukemia (RBL)-2H3 cells

Biochem/physiol Actions

4-Nitrophenyl N-acetyl-β-D-glucosaminide (NP-GlcNAc) is a widely used hexosaminidase substrate. Enzymatic action cleaves the glycosidic bond and forms 4-nitrophenolate (pNP) which is measured at 405 nm. NP-GlcNAc can also be used in combination with diethylaminoethyl-a-cyclodextrin (DEn-CD) for a rapid and accurate rate assay method for b-N-acetylglucosaminidase. The cyclodextrin derivative is used as an additive to ionize 4-nitrophenol to yellow-colored 4-nitrophenoxide at a pH near 5, the pH optimum for the enzyme.

Substrates

Chromogenic substrate for N-acetyl-glucosaminidase.

Safety Information

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