N-Acetylneuraminic acid

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N-Acetylneuraminic acid
IUPAC name	5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Identifiers
CAS number	131-48-6
PubChem	439197
MeSH	N-Acetylneuraminic+Acid
SMILES	OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO
Properties
Molecular formula	C11H19NO9
Molar mass	309.27 g mol−1
Exact mass	309.105981
Appearance	White crystalline powder
Melting point	186°C (decomposes)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in mammalian cells.

This negatively charged residue is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, such as gangliosides, a crucial component of neuronal membranes found in the brain.

Along with involvement in preventing infections (mucus associated with mucous membranes — mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemaglutinin (an early step in contracting the flu).

See also

• Neuraminic acid
• Sialic acid
• N-Glycolylneuraminic acid