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Merck
CN

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:
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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Product Name

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

InChI key

OMRLTNCLYHKQCK-DHGKCCLASA-N

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

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

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

Quality Level

300

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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.

General description

Chromogenic substrate for N-acetyl-glucosaminidase.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000490991
0000490991
0000491062
0000491066
0000491065

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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
Chromogenic carbamate and acetal substrates for glycosaminidases
Chibba A, et al.
Carbohydrate Chemistry, 549-558 null
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
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%.
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