N9376
4-Nitrophenyl N-acetyl-β-D-glucosaminide
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:
Molecular Weight:
342.30
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
222-398-7
MDL number:
Beilstein/REAXYS Number:
96193
Product Name
4-Nitrophenyl N-acetyl-β-D-glucosaminide, ≥99% (TLC)
Quality Level
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
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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Related Content
Instructions
Kenji Osumi et al.
Carbohydrate research, 339(15), 2633-2635 (2004-10-13)
We found that the recombinant endo-beta-N-acetylglucosaminidase of Mucor hiemalis (Endo-M) expressed in Candida boidinii had the transglycosylation activity of transferring a bisecting hybrid-type oligosaccharide from an ovalbumin glycopeptide to the acceptor (p-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside) in a good yield of 43%.
Jin-Jin Xie et al.
International journal of biological macromolecules, 39(4-5), 159-164 (2006-07-04)
Chemical modification of p-chloromercuribenzoate (PCMB) on beta-N-acetyl-d-glucosaminidase (NAGase, EC 3.2.1.52) from green crab (Scylla serrata) has been studied. The results show that sulfhydryl group is essential for the activity of the enzyme. Inhibitory kinetics of the enzyme by mercuric chloride
J Kukidome et al.
The Tohoku journal of experimental medicine, 194(1), 23-34 (2001-09-15)
COLO 201, human colon adenocarcinoma cells were incubated with artificial primers, p-nitrophenyl-glycoside derivatives at 1.0 mmol (mM) in the medium containing 10% fetal bovine serum to detect sugar chain elongation. However, when p-nitrophenyl-beta-N-acetylglucosamine (beta-GlcNAc-PNP) was added, the medium changed color
Global Trade Item Number
| SKU | GTIN |
|---|---|
| N9376-1G | 04061835516209 |
| N9376-10MG | 04061831159837 |
| N9376-250MG | 04061835558193 |
| N9376-100MG | 04061835518210 |
| N9376-500MG | 04061834118794 |
| N9376-50MG | 04061831159844 |