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A0812

N-Acetylneuraminic acid

≥95% anhydrous basis, synthetic

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C11H19NO9
Numéro CAS:
131-48-6
Poids moléculaire :
309.27
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24890457
EC Number:
205-023-1
Beilstein/REAXYS Number:
1716283
MDL number:
MFCD00006620
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biological source

synthetic

type

Type IV-S

assay

≥95% anhydrous basis

form

powder

color

white to off-white

mp

184-186  °C

solubility

H2O: ~50 mg/mL

application(s)

advanced drug delivery

storage temp.

−20°C

SMILES string

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

InChI key

SQVRNKJHWKZAKO-PFQGKNLYSA-N

Application

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.

Biochem/physiol Actions

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.

Other Notes

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

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Classe de stockage

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000474172
0000474172
0000474173
0000474173
0000474170

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Contenu apparenté

Product Information Sheet - A0812

Product Information Sheet

Kavita Agarwal et al.
PLoS biology, 18(8), e3000788-e3000788 (2020-08-26)
Women with bacterial vaginosis (BV), an imbalance of the vaginal microbiome, are more likely to be colonized by potential pathogens such as Fusobacterium nucleatum, a bacterium linked with intrauterine infection and preterm birth. However, the conditions and mechanisms supporting pathogen
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
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
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