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N9376

Sigma-Aldrich

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:
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

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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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ken-ichi Kanno et al.
Lab on a chip, 2(1), 15-18 (2004-04-22)
Glycosidase-promoted hydrolysis was performed in a microreaction channel. The result was compared with the reaction in a micro-test tube. Transgalactosylation on p-nitrophenyl-2-acetamide-2-deoxy-beta-D-glucopyranoside was also examined in a microreaction channel, because transglycosylation is a useful method for oligosaccharide synthesis. We examined
Femke Waanders et al.
American journal of kidney diseases : the official journal of the National Kidney Foundation, 53(1), 16-25 (2008-10-01)
Tubulointerstitial damage plays an important role in chronic kidney disease (CKD) with proteinuria. Urinary kidney injury molecule 1 (KIM-1) reflects tubular KIM-1 and is considered a sensitive biomarker for early tubular damage. We hypothesized that a decrease in proteinuria by
Yajun Zhou et al.
FEMS microbiology letters, 363(12) (2016-05-18)
We purified a chitinase from pilei extractions of Coprinopsis cinerea fruiting bodies by ammonium sulfate precipitation and CM Sepharose cation exchange chromatography. MALDI-TOF/TOF MS analysis characterized this purified chitinase as a putative class V chitinase, ChiB1. ChiB1 hydrolyzed colloidal chitin
K Masaki et al.
Journal of protein chemistry, 20(2), 107-113 (2001-09-21)
Bombyx mori lysozyme is 10 amino acids shorter than hen egg-white lysozyme, which is a typical c-type lysozyme. It was expressed by using the methylotrophic yeast Pichia pastoris. The thermal stability and the enzymatic activity of the Bombyx mori lysozyme
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
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