A0812

Sigma-Aldrich

N-Acetylneuraminic acid

synthetic, ≥95%

Synonym(s):
NANA, NAN, 5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, Sialic acid
Empirical Formula (Hill Notation):
C11H19NO9
CAS Number:
Molecular Weight:
309.27
Beilstein/REAXYS Number:
1716283
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

synthetic

type

Type IV-S

assay

≥95%

form

powder

mp

184-186  °C

solubility

H2O: ~50 mg/mL

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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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.

Packaging

1 g in poly bottle
25, 100, 250 mg in poly bottle

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

Eye Irrit. 2

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 2

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
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...
Eric R Vimr et al.
Microbiology and molecular biology reviews : MMBR, 68(1), 132-153 (2004-03-10)
Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity, and microbes have evolved various strategies for subverting this...
Articles
Review article and products for sialic acid synthesis and signaling.
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