N-acetylneuraminic acid

N-Acetylneuraminic acid
Names

IUPAC name 5-(acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Identifiers
CAS Number	131-48-6^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:61599^Y
ChemSpider	392681^Y
ECHA InfoCard	100.004.568
MeSH	N-Acetylneuraminic+Acid
PubChem	439197
InChI 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^Y Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N^Y InChI=1/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 Key: SQVRNKJHWKZAKO-YRMXFSIDBI
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
Chemical formula	C₁₁H₁₉NO₉
Molar mass	309.273 g/mol
Appearance	White crystalline powder
Melting point	186 °C (367 °F; 459 K) (decomposes)
Pharmacology
ATC code	M09AX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
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 hemagglutinin (an early step in acquiring influenzavirus infection).

Neu5Ac is also important in the biology of a member of pathogenic bacteria as it can used either as a nutrient, providing both carbon and nitrogen to the bacterium, or in some pathogens, can be activated and placed on the cell surface. Bacteria have evolved transporters for Neu5Ac to enable them to capture it from their environment and a number of these have been characterised including the NanT protein from Escherichia coli, the SiaPQM TRAP transporter from Haemophilus influenzae and the SatABCD ABC transporter from Haemophilus ducreyi.

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