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Merck

N2127

4-Nitrophenyl α-D-mannopyranoside

α-mannosidase substrate, chromogenic, ≥98% (TLC), powder

Synonym(s):

4-Nitrophenyl a-D-mannopyranoside, 4-Nitrophenyl alpha-D-mannopyranoside, pNP-alpha-D-Man, pNPalphaMan

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About This Item

Empirical Formula (Hill Notation):
C12H15NO8
CAS Number:
10357-27-4
Molecular Weight:
301.25
NACRES:
NA.32
PubChem Substance ID:
24897554
UNSPSC Code:
12352204
EC Number:
233-776-6
MDL number:
MFCD00066002
Beilstein/REAXYS Number:
92210

Key Documents

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Product Name

4-Nitrophenyl α-D-mannopyranoside, α-mannosidase substrate

InChI key

IFBHRQDFSNCLOZ-GCHJQGSQSA-N

InChI

1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11+,12+/m1/s1

SMILES string

OC[C@H]1O[C@H](Oc2ccc(cc2)[N+]([O-])=O)[C@@H](O)[C@@H](O)[C@@H]1O

assay

≥98% (TLC)

form

powder

solubility

DMF: 50 mg/mL

storage temp.

−20°C

Quality Level

300

General description

4-Nitrophenyl α-D-mannopyranoside is a chromogenic substrate for α-mannosidase.

Application

4-Nitrophenyl α-D-mannopyranoside has been used as a substrate for α-mannosidase in hydrolase activity assay.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000507520
0000507519
0000507518
0000507517
0000507517

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I Sielezneff et al.
Chirurgie; memoires de l'Academie de chirurgie, 124(2), 159-164 (1999-06-01)
Peritoneal colonization is a crucial event in the pathogenesis of peritonitis and its local complications. Adherence to the serosal mesothelium is mediated in a number of microorganisms derived from the digestive tract (especially E. coli) by type-1 fimbriae which have
Yanping Zhu et al.
Nature chemical biology, 6(2), 125-132 (2010-01-19)
Colonic bacteria, exemplified by Bacteroides thetaiotaomicron, play a key role in maintaining human health by harnessing large families of glycoside hydrolases (GHs) to exploit dietary polysaccharides and host glycans as nutrients. Such GH family expansion is exemplified by the 23
R Madiyalakan et al.
European journal of cancer & clinical oncology, 23(7), 901-906 (1987-07-01)
A modified procedure was developed for the determination of UDP-galactose: 2-acetamido-2-deoxy-glucopyranoside beta-(1----4)-galactosyltransferase (GT) in human serum which employed the synthetic substrates p-nitrophenyl 6-0-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-D-galactopyranoside and p-nitrophenyl 6-0-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D- mannopyranoside as acceptors. The enzyme products were identified by thin layer chromatography with authentic
S Howard et al.
Biochemical and biophysical research communications, 238(3), 896-898 (1997-10-23)
The stereochemical course of the hydrolyses catalysed by two alpha-mannosidases has been determined directly by 1H NMR. Synthetic substrates were incubated with the enzymes and the anomeric configuration of the initially formed product was ascertained in each case by observation
S J Hamodrakas et al.
International journal of biological macromolecules, 11(1), 17-22 (1989-02-01)
Molecular models for the complex formed between the lectin concanavalin A (Con A) and the saccharide derivative 4'-nitrophenyl-alpha-D-mannopyranoside (alpha-PNM) are presented, combining evidence from 1H-n.m.r. measurements, semi-empirical energy calculations and interactive graphics modelling. The models are in good agreement with
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