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N9376

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

Name: 4-Nitrophenyl N-acetyl-β-<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

Beilstein:

96193

EC Number:

222-398-7

MDL number:

MFCD00063696

UNSPSC Code:

12352204

PubChem Substance ID:

24897896

NACRES:

NA.32

Pricing and availability is not currently available.

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

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1 of 4

This Item	N7006	N8759	N4264
N9376 4-Nitrophenyl N-acetyl-β-D-glucosaminide	N7006 4-Nitrophenyl β-D-glucopyranoside	N8759 4-Nitrophenyl N-acetyl-α-D-glucosaminide	N4264 4-Nitrophenyl N-acetyl-α-D-galactosaminide
assay ≥99% (TLC)	assay ≥98% (TLC)	assay ≥98%	assay ≥98% (TLC)
solubility water: 5 mg/mL, clear, colorless to very faintly yellow	solubility water: 50 mg/mL, clear to very slightly hazy	solubility warm ethanol: acetic acid (1:1): 20 mg/mL, clear, colorless to faintly yellow	solubility DMF: 25 mg/mL, clear, colorless to faintly yellow
Quality Level 300	Quality Level 300	Quality Level 100	Quality Level 200
form powder	form powder	form powder	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
impurities ≤0.05% Free p-nitrophenol	impurities -	impurities -	impurities -

Application

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

as a substrate to assay N-acetyl-β-D-glucosaminidase (NAG)[1]
as a substrate to study chitinase ChiB1 activity[2]
to assess degranulation using rat basophilic leukemia (RBL)-2H3 cells[3]

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.[4] 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.

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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