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N8759

Sigma-Aldrich

4-Nitrophenyl N-acetyl-α-D-glucosaminide

≥98%, powder

Synonym(s):

p-Nitrophenyl 2-acetamido-2-deoxy-α-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C14H18N2O8
CAS Number:
10139-02-3
Molecular Weight:
342.30
EC Number:
233-392-9
MDL number:
MFCD00006592
UNSPSC Code:
12352204
PubChem Substance ID:
24897691
NACRES:
NA.32

product name

4-Nitrophenyl N-acetyl-α-D-glucosaminide, ≥98%

Assay

≥98%

form

powder

solubility

warm ethanol: acetic acid (1:1): 20 mg/mL, clear, colorless to 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-KSTCHIGDSA-N

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Application

4-Nitrophenyl N-acetyl-α-D-glucosaminide is used as a substrate for determining the hydrolysing activities of pnp-glycopyranosides in the gut of larval and adult Psacothea hilaris.

Biochem/physiol Actions

4-Nitrophenyl N-acetyl-α-D-glucosaminide is used as a substrate for analysing β-hexoaminidase activity at 37°C and analysed at 405 nm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Study of subcellular localization and proteolysis of ataxin-3
Pozzi C, et al.
Neurobiology of Disease, 30(2), 190-200 (2008)
Diet and carbohydrate digestion in the yellow-spotted longicorn beetle Psacothea hilaris
Scrivener AM, et al.
Journal of Insect Physiology, 43(11), 1039-1052 (1997)
N O Keyhani et al.
The Journal of biological chemistry, 271(52), 33414-33424 (1996-12-27)
Chitin catabolism in Vibrio furnissii comprises several signal transducing systems and many proteins. Two of these enzymes are periplasmic and convert chitin oligosaccharides to GlcNAc and (GlcNAc)2. One of these unique enzymes, a chitodextrinase, designated EndoI, is described here. The
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%.
S Drouillard et al.
The Biochemical journal, 328 ( Pt 3), 945-949 (1998-02-07)
The stereochemistry of the reaction catalysed by Serratia marcescens chitobiase was determined by HPLC separation of the anomers of N-acetylglucosamine produced during the hydrolysis of p-nitrophenyl N-acetyl-beta-d-glucosaminide (PNP-GlcNAc). In the early stages of the reaction, the beta-anomer was found to
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