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Key Documents

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:
Poids moléculaire :
342.30
Numéro Beilstein :
96193
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352204
ID de substance PubChem :
Nomenclature NACRES :
NA.32

product name

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

Niveau de qualité

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
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
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%.
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

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