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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%

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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)
Andrzej Temeriusz et al.
Carbohydrate research, 341(15), 2581-2590 (2006-09-05)
The X-ray diffraction analysis of N-o-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine (1), N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, and their N-acetyl derivatives was performed. The sugar moieties always adopt (4)C1 conformations, however, due to crystal packing forces they are always slightly distorted. It was found that except N-acetyl, N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine
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
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
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