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N9376

Sigma-Aldrich

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

chromogenic, ≥99% (TLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C14H18N2O8
Numéro CAS:
3459-18-5
Poids moléculaire :
342.30
Numéro Beilstein :
96193
Numéro CE :
222-398-7
Numéro MDL:
MFCD00063696
Code UNSPSC :
12352204
ID de substance PubChem :
24897896
Nomenclature NACRES :
NA.32

product name

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

Pureté

≥99% (TLC)

Forme

powder

Impuretés

≤0.05% Free p-nitrophenol

Solubilité

water: 5 mg/mL, clear, colorless to very faintly yellow

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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

Actions biochimiques/physiologiques

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.

Substrats

Chromogenic substrate for N-acetyl-glucosaminidase.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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