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N9376

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

Name: 4-Nitrophenyl N-acetyl-&#946;-<SC>D</SC>-glucosaminide
Brand: SIGMA

chromogenic, ≥99% (TLC), powder

Synonym(s):

4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):

C₁₄H₁₈N₂O₈

CAS Number:

3459-18-5

Molecular Weight:

342.30

NACRES:

NA.32

PubChem Substance ID:

24897896

UNSPSC Code:

12352204

EC Number:

222-398-7

MDL number:

MFCD00063696

Beilstein/REAXYS Number:

96193

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Properties

Product Name

4-Nitrophenyl N-acetyl-β-D-glucosaminide, ≥99% (TLC)

Quality Level

300

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

General description

Chromogenic substrate for N-acetyl-glucosaminidase.

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.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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