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A2388

Sigma-Aldrich

N-Acetylneuraminic acid

≥98% (HPLC), from Escherichia coli

Sinónimos:

5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, NAN, NANA, Sialic acid

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About This Item

Fórmula empírica (notación de Hill):
C11H19NO9
Número de CAS:
131-48-6
Peso molecular:
309.27
Beilstein:
1716283
Número CE:
205-023-1
Número MDL:
MFCD00006620
Código UNSPSC:
12352201
ID de la sustancia en PubChem:
24890650
NACRES:
NA.25

origen biológico

Escherichia coli

tpo

Type VI

Ensayo

≥98% (HPLC)

Formulario

powder

actividad óptica

[α]20/D -34.0 to -30.0 °, c = 1% in water

técnicas

HPLC: suitable

color

white to off-white

mp

184-186  °C

solubilidad

water: 50 mg/mL, clear, colorless

temp. de almacenamiento

−20°C

cadena SMILES

O[C@@]1(O[C@@]([C@@H]([C@H](C1)O)NC(C)=O)([H])[C@@H]([C@@H](CO)O)O)C(O)=O

InChI

1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1

Clave InChI

SQVRNKJHWKZAKO-PFQGKNLYSA-N

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Categorías relacionadas

Aplicación

N-Acetylneuraminic acid (NANA, Neu5Ac) is a major component of glycoconjugates such as glycolipids, glycoproteins and proteoglycans (sialogylcoproteins) where it confers selective binding characteristics to the glycosylated component. Neu5Ac is used to study its biochemistry, metabolism and uptake in vivo and in vitro. Neu5Ac is used in the development of nanocarriers.

Acciones bioquímicas o fisiológicas

Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.

Otras notas

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H319

Clasificaciones de peligro

Eye Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000440745
0000440739
0000440742
0000440742
0000440739

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Alexander T Baker et al.
Science advances, 5(9), eaax3567-eaax3567 (2019-09-14)
Adenoviruses are clinically important agents. They cause respiratory distress, gastroenteritis, and epidemic keratoconjunctivitis. As non-enveloped, double-stranded DNA viruses, they are easily manipulated, making them popular vectors for therapeutic applications, including vaccines. Species D adenovirus type 26 (HAdV-D26) is both a
Fiona E Fleming et al.
Journal of virology, 88(8), 4558-4571 (2014-02-07)
N-acetyl- and N-glycolylneuraminic acids (Sia) and α2β1 integrin are frequently used by rotaviruses as cellular receptors through recognition by virion spike protein VP4. The VP4 subunit VP8*, derived from Wa rotavirus, binds the internal N-acetylneuraminic acid on ganglioside GM1. Wa
Xiaoli Xiong et al.
Nature, 499(7459), 496-499 (2013-06-22)
Of the 132 people known to have been infected with H7N9 influenza viruses in China, 37 died, and many were severely ill. Infection seems to have involved contact with infected poultry. We have examined the receptor-binding properties of this H7N9
Anwar M Hashem et al.
PloS one, 8(2), e55428-e55428 (2013-02-21)
Vaccination is the most effective prophylactic method for preventing influenza. Quantification of influenza vaccine antigens is critically important before the vaccine is used for human immunization. Currently the vaccine antigen quantification relies on hemagglutinin content quantification, the key antigenic component
Ruth Huizinga et al.
Journal of immunology (Baltimore, Md. : 1950), 191(11), 5636-5645 (2013-10-30)
Campylobacter jejuni is the most common bacterial cause of human gastroenteritis and often precedes development of Guillain-Barré syndrome (GBS), a life-threatening paralytic disease. The incorporation of the carbohydrate sialic acid into C. jejuni lipooligosaccharides (LOS) is associated with increased severity
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Protocolos

Enzymatic Assay of Neuraminidase

Enzymatic Assay of Neuraminidase applies to products that have a specification for neuraminidase content by enzymatic determination.

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