A2388

N-Acetylneuraminic acid

Name: N-Acetylneuraminic acid
Brand: SIGMA

≥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 CAS:

131-48-6

Peso molecular:

309.27

UNSPSC Code:

12352201

NACRES:

NA.25

PubChem Substance ID:

24890650

EC Number:

205-023-1

Beilstein/REAXYS Number:

1716283

MDL number:

MFCD00006620

Nombre del producto

N-Acetylneuraminic acid, ≥98% (HPLC), from Escherichia coli

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

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

biological source

Escherichia coli

type

Type VI

assay

≥98% (HPLC)

form

powder

optical activity

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

technique(s)

HPLC: suitable

color

white to off-white

mp

184-186 °C

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

300

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Categorías relacionadas

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

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.

pictograms

GHS07

signalword

Warning

hcodes

H319

pcodes

P264 - P280 - P305 + P351 + P338 - P337 + P313

Hazard Classifications

Eye Irrit. 2

Clase de almacenamiento

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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Human adenovirus type 26 uses sialic acid-bearing glycans as a primary cell entry receptor.

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

Relative roles of GM1 ganglioside, N-acylneuraminic acids, and α2β1 integrin in mediating rotavirus infection.

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

Structural determinants for naturally evolving H5N1 hemagglutinin to switch its receptor specificity.

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

Serum amyloid P is a sialylated glycoprotein inhibitor of influenza A viruses.

Emma R Job et al.

PloS one, 8(3), e59623-e59623 (2013-04-02)

Members of the pentraxin family, including PTX3 and serum amyloid P component (SAP), have been reported to play a role in innate host defence against a range of microbial pathogens, yet little is known regarding their antiviral activities. In this

Renal handling of free sialic acid in normal humans and patients with Salla disease or renal disease.

R Seppala et al.

Laboratory investigation; a journal of technical methods and pathology, 63(2), 197-203 (1990-08-01)

The renal handling of free sialic acid, a negatively charged sugar, was investigated in normal humans and in patients with impaired sialic acid metabolism or impaired renal function. A sensitive assay for sialic acid, based upon the specific degradation of

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