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Key Documents

N1516

Sigma-Aldrich

2-O-(p-Nitrophenyl)-α-D-N-acetylneuraminic acid

chromogenic, ≥95%, powder

Synonym(s):

PNP-a-NeuNAc

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About This Item

Empirical Formula (Hill Notation):
C17H22N2O11
CAS Number:
Molecular Weight:
430.36
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

2-O-(p-Nitrophenyl)-α-D-N-acetylneuraminic acid, ≥95%

Quality Level

assay

≥95%

form

powder

impurities

~0.5% free p-nitrophenol

solubility

methanol: 25 mg/mL, clear, colorless to faintly yellow

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(=O)NC1C(O)CC(OC1C(O)C(O)CO)(Oc2ccc(cc2)N(=O)=O)C(O)=O

InChI

1S/C17H22N2O11/c1-8(21)18-13-11(22)6-17(16(25)26,30-15(13)14(24)12(23)7-20)29-10-4-2-9(3-5-10)19(27)28/h2-5,11-15,20,22-24H,6-7H2,1H3,(H,18,21)(H,25,26)

InChI key

OICUZSPXIJAAEA-UHFFFAOYSA-N

Application

2-O-(p-Nitrophenyl)-α-D-N-acetylneuraminic acid may be used as a substrate to measure sialidase enzyme activity.

Biochem/physiol Actions

2-O-(p-Nitrophenyl)-α-D-N-acetylneuraminic acid serves as a sialyl donor in enzyme-catalyzed trans-sialylation.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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Synthesis of p-nitrophenyl 5-acetamido-3,5-dideoxy-alpha-D-glycero-D-galacto-2-nonulopyranosid onic acid, a chromogenic substrate for sialidases.
V Eschenfelder et al.
Carbohydrate research, 162(2), 294-297 (1987-05-01)
X Guo et al.
The Biochemical journal, 296 ( Pt 2), 291-292 (1993-12-01)
When the time course of the hydrolysis of identical solutions of p-nitrophenyl N-acetyl-alpha-D-neuraminide by Salmonella typhimurium neuraminidase is monitored by u.v. and by its optical rotation, the rotation change is synchronous with, or even marginally in advance of, the absorbance
Pascal Maurice et al.
Scientific reports, 6, 38363-38363 (2016-12-06)
Neuraminidase 1 (NEU1) is a lysosomal sialidase catalyzing the removal of terminal sialic acids from sialyloconjugates. A plasma membrane-bound NEU1 modulating a plethora of receptors by desialylation, has been consistently documented from the last ten years. Despite a growing interest

Articles

Review article and products for sialic acid synthesis and signaling.

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