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Merck
CN

N1516

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:
26112-88-9
Molecular Weight:
430.36
UNSPSC Code:
12352204
PubChem Substance ID:
24897497
NACRES:
NA.32
MDL number:
MFCD00132944

Key Documents

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Product Name

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

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

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

Quality Level

200

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
GHS06,GHS08

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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
054K5009V
054K5009
035H5018
117H5115
114H5024

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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)
Yao Guo et al.
Journal of biotechnology, 170, 60-67 (2013-12-03)
This study examined a recombinant Pasteurella multocida sialyltransferase exhibiting dual trans-sialidase activities. The enzyme catalyzed trans-sialylation using either 2-O-(p-nitrophenyl)-α-d-N-acetylneuraminic acid or casein glycomacropeptide (whey protein) as the sialyl donor and lactose as the acceptor, resulting in production of both 3'-sialyllactose
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
Bentley Lim et al.
Cell, 169(3), 547-558 (2017-04-22)
The gut microbiota is implicated in numerous aspects of health and disease, but dissecting these connections is challenging because genetic tools for gut anaerobes are limited. Inducible promoters are particularly valuable tools because these platforms allow real-time analysis of the
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

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