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Key Documents

A9646

Sigma-Aldrich

N-Acetylneuraminic acid

from sheep submaxillary glands, ≥99%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H19NO9
Numéro CAS:
Poids moléculaire :
309.27
Numéro Beilstein :
1716283
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352201
ID de substance PubChem :

Source biologique

sheep submaxillary glands

Type

Type VIII

Pureté

≥99%

Température de stockage

−20°C

Chaîne 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

Clé InChI

SQVRNKJHWKZAKO-PFQGKNLYSA-N

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Actions biochimiques/physiologiques

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.

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Youngsoo Sohn et al.
BMB reports, 46(3), 157-162 (2013-03-27)
Human α-galactosidase A (GLA) has been used in enzyme replacement therapy for patients with Fabry disease. We expressed recombinant GLA from Chinese hamster ovary cells with very high productivity. When compared to an approved GLA (agalsidase beta), its size and
Kannan Tharakaraman et al.
Cell, 153(7), 1475-1485 (2013-06-12)
Of the factors governing human-to-human transmission of the highly pathogenic avian-adapted H5N1 virus, the most critical is the acquisition of mutations on the viral hemagglutinin (HA) to "quantitatively switch" its binding from avian to human glycan receptors. Here, we describe
Sasirekha Ramani et al.
Journal of virology, 87(13), 7255-7264 (2013-04-26)
Naturally occurring bovine-human reassortant rotaviruses with a P[11] VP4 genotype exhibit a tropism for neonates. Interaction of the VP8* domain of the spike protein VP4 with sialic acid was thought to be the key mediator for rotavirus infectivity. However, recent
T A Timofeeva et al.
Voprosy virusologii, 58(1), 24-27 (2013-06-22)
The influenza virus hemagglutinin (HA) is an envelope virus glycoprotein responsible for the attachment of the virus particles to cells via binding terminal sialic acid residues of cell surface oligosaccharides. In our previous works on influenza A virus escape mutants
Wei Zhang et al.
Journal of virology, 87(10), 5949-5958 (2013-03-22)
Influenza A virus uses sialic acids as cell entry receptors, and there are two main receptor forms, α2,6 linkage or α2,3 linkage to galactose, that determine virus host ranges (mammalian or avian). The receptor binding hemagglutinins (HAs) of both 1918

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