N2127

4-Nitrophenyl α-D-mannopyranoside

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

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

Beilstein:

92210

EC Number:

233-776-6

MDL number:

MFCD00066002

UNSPSC Code:

12352204

PubChem Substance ID:

24897554

NACRES:

NA.32

Key Documents

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Product Name

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

Quality Level

300

Assay

≥98% (TLC)

form

powder

solubility

DMF: 50 mg/mL

storage temp.

−20°C

SMILES string

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

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

InChI key

IFBHRQDFSNCLOZ-GCHJQGSQSA-N

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This Item	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

General description

4-Nitrophenyl α-D-mannopyranoside is a chromogenic substrate for α-mannosidase.[1]

Application

4-Nitrophenyl α-D-mannopyranoside has been used as a substrate for α-mannosidase[2] in hydrolase activity assay.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

Calnexin/Calreticulin and Assays Related to N-Glycoprotein Folding In Vitro.

Yoshito Ihara et al.

Methods in molecular biology (Clifton, N.J.), 2132, 295-308 (2020-04-20)

Calnexin (CNX) and calreticulin (CRT) are ER-resident lectin-like molecular chaperones involved in the quality control of secretory or membrane glycoproteins. They can exert molecular chaperone functions via specific binding to the early processing intermediates of Glc1Man9GlcNAc2 oligosaccharides of N-glycoproteins. CNX

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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