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Merck

A2388

N-Acetylneuraminic acid

≥98% (HPLC), from Escherichia coli

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H19NO9
CAS Number:
131-48-6
Molecular Weight:
309.27
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24890650
EC Number:
205-023-1
Beilstein/REAXYS Number:
1716283
MDL number:
MFCD00006620

Key Documents

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Product Name

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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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

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000521078
0000521078
0000515250
0000515249
0000515251

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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
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
Inessa Schwab et al.
Nature reviews. Immunology, 13(3), 176-189 (2013-02-16)
Intravenous immunoglobulin (IVIG) preparations comprise pooled IgG antibodies from the serum of thousands of donors and were initially used as an IgG replacement therapy in immunocompromised patients. Since the discovery, more than 30 years ago, that IVIG therapy can ameliorate
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