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N1516

Sigma-Aldrich

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

chromogenic, ≥95%, powder

Synonyme(s) :

PNP-a-NeuNAc

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About This Item

Formule empirique (notation de Hill):
C17H22N2O11
Numéro CAS:
26112-88-9
Poids moléculaire :
430.36
Numéro MDL:
MFCD00132944
Code UNSPSC :
12352204
ID de substance PubChem :
24897497
Nomenclature NACRES :
NA.32

product name

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

Niveau de qualité

200

Pureté

≥95%

Forme

powder

Impuretés

~0.5% free p-nitrophenol

Solubilité

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

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

OICUZSPXIJAAEA-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (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)
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
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
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
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

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