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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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biological source

Escherichia coli

Quality Level

300

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

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

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Related Categories

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)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A2388-250MG: + A2388-25MG: + A2388-BULK: + A2388-10MG: + A2388-1G: + A2388-VAR: + A2388-100MG:

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Peter Svenssen Munksgaard et al.
Infection and immunity, 82(6), 2219-2228 (2014-03-20)
Leukotoxin (LtxA) from Aggregatibacter actinomycetemcomitans is known to target and lyse β2-integrin-expressing cells such as polymorphonuclear leukocytes and macrophages. LtxA is an important virulence factor that facilitates chronic inflammation and is strongly associated with a fast-progressing form of periodontitis caused
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
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
Katharine M Ng et al.
Nature, 502(7469), 96-99 (2013-09-03)
The human intestine, colonized by a dense community of resident microbes, is a frequent target of bacterial pathogens. Undisturbed, this intestinal microbiota provides protection from bacterial infections. Conversely, disruption of the microbiota with oral antibiotics often precedes the emergence of
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
View All Related Papers

Protocols

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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