N2127

4-Nitrophenyl α-D-mannopyranoside

Name: 4-Nitrophenyl α-<SC>D</SC>-mannopyranoside
Brand: SIGMA

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

Sinónimos:

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

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Fórmula empírica (notación de Hill):

C₁₂H₁₅NO₈

Número CAS:

10357-27-4

Peso molecular:

301.25

NACRES:

NA.32

PubChem Substance ID:

24897554

UNSPSC Code:

12352204

EC Number:

233-776-6

MDL number:

MFCD00066002

Beilstein/REAXYS Number:

92210

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Nombre del producto

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

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Este artículo	N1268	N5885	N1884
Sigma-Aldrich N2127 4-Nitrophenyl α-D-mannopyranoside	Sigma-Aldrich N1268 4-Nitrophenyl β-D-mannopyranoside	Sigma-Aldrich N5885 4-Nitrophenyl α-D-maltoside	Sigma-Aldrich N1884 4-Nitrophenyl β-D-maltoside
assay ≥98% (TLC)	assay ≥98%	assay ≥99% (TLC)	assay ≥98% (TLC)
solubility DMF: 50 mg/mL	solubility water: 10 mg/mL, clear, colorless to very faintly green	solubility water: 49.00-51.00 mg/mL, clear, colorless to light yellow	solubility water: 19.60-20.40 mg/mL, clear, colorless to light yellow
Quality Level 300	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C

Application

4-Nitrophenyl α-D-mannopyranoside has been used as a substrate for α-mannosidase[1] in hydrolase activity assay.[2]

General description

4-Nitrophenyl α-D-mannopyranoside is a chromogenic substrate for α-mannosidase.[3]

Clase de almacenamiento

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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A long-wavelength fluorescent substrate for continuous fluorometric determination of alpha-mannosidase activity: resorufin alpha-D-mannopyranoside.

Daniel J Coleman et al.

Analytical biochemistry, 399(1), 7-12 (2009-12-23)

A simple and reliable continuous assay for measurement of alpha-mannosidase activity is described and demonstrated for analysis with two recombinant human enzymes using the new substrate resorufin alpha-d-mannopyranoside (Res-Man). The product of enzyme reaction, resorufin, exhibits fluorescence emission at 585

The crystal structure of the complexes of concanavalin A with 4'-nitrophenyl-alpha-D-mannopyranoside and 4'-nitrophenyl-alpha-D-glucopyranoside.

P N Kanellopoulos et al.

Journal of structural biology, 116(3), 345-355 (1996-05-01)

Concanavalin A (Con A) is the best-known plant lectin and has important in vitro biological activities arising from its specific saccharide-binding ability. Its exact biological role still remains unknown. The complexes of Con A with 4'-nitrophenyl-alpha-D-mannopyranoside (alpha-PNM) and 4'-nitrophenyl-alpha-D-glucopyranoside (alpha-PNG)

Characterization of a specific alpha-mannosidase involved in oligosaccharide processing in Saccharomyces cerevisiae.

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

Frontal affinity chromatography of ovalbumin glycoasparagines on a concanavalin A-sepharose column. A quantitative study of the binding specificity of the lectin.

Y Ohyama et al.

The Journal of biological chemistry, 260(11), 6882-6887 (1985-06-10)

The interactions of Sepharose 4B-immobilized concanavalin A (ConA) with 10 glycoasparagines derived from ovalbumin were investigated quantitatively by frontal affinity chromatography. In this method, a carbohydrate solution is applied continuously to a ConA-Sepharose column and the retardation of the elution

Models of binding of 4'-nitrophenyl alpha-D-mannopyranoside to the lectin concanavalin A.

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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