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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
0000507518

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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
S Jelinek-Kelly et al.
The Journal of biological chemistry, 260(4), 2253-2257 (1985-02-25)
Fractionation of a crude extract from Saccharomyces cerevisiae X-2180 on Sepharose 6B in the presence of 0.5% Triton X-100 resolves two enzyme fractions containing alpha-mannosidase activity. Fraction I which is excluded from the gel contains alpha-mannosidase activity toward both p-nitrophenyl-alpha-D-mannopyranoside
Synthesis and evaluation of two mannosamine-derived lactone-type inhibitors of snail beta-mannosidase
Terinek M and Vasella A
Tetrahedron Asymmetry, 16, 449-469 (2005)
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
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
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