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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)

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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)
Study of subcellular localization and proteolysis of ataxin-3
Pozzi C, et al.
Neurobiology of Disease, 30(2), 190-200 (2008)
Ken-ichi Kanno et al.
Lab on a chip, 2(1), 15-18 (2004-04-22)
Glycosidase-promoted hydrolysis was performed in a microreaction channel. The result was compared with the reaction in a micro-test tube. Transgalactosylation on p-nitrophenyl-2-acetamide-2-deoxy-beta-D-glucopyranoside was also examined in a microreaction channel, because transglycosylation is a useful method for oligosaccharide synthesis. We examined
E Frändberg et al.
The Journal of applied bacteriology, 76(3), 259-263 (1994-03-01)
Three methods of quantifying chitinase activity were compared. The activities of crude chitinases of 10 bacterial isolates from different environments were estimated in terms of (1) the release of p-nitrophenol from the chromogenic chito-oligosaccharide analogues, p-nitrophenyl-beta-D-N,N'-diacetylchitobiose, p-nitrophenyl-N-acetyl-beta-D-glucosamine and p-nitrophenyl-beta-D-N,N',N"-triacetylchitotriose, (2)
T Usui et al.
Biochimica et biophysica acta, 953(2), 179-184 (1988-03-23)
Transchitooligosylation from (GlcNAc)5 to the 4-position of PNP-GlcNAc was efficiently induced through lysozyme catalysis in an aqueous solution containing methanol with a high concentration. Use of the aqueous methanol system in this reaction not only guaranteed solubility of PNP-GlcNAc substrate
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