N- acetyl neuraminic acid

Structural formula
	N -acetylneuraminic acid, β- anomer
General
Surname	N- acetyl neuraminic acid
other names	NANA; NewNAc; New5Ac; ACETYLNEURAMINIC ACID ( INCI ) ;
Molecular formula	C 11 H 19 NO 9
Brief description	white solid
External identifiers / databases
EC number	205-023-1
ECHA InfoCard	100,004,568
PubChem	439197
ChemSpider	392681
Wikidata	Q310828
properties
Molar mass	309.27 g mol −1
Physical state	firmly
boiling point	184–186 ° C (decomposition)
solubility	moderate in water (50 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N- acetylneuraminic acid (abbreviated NANA from English: N - a cetyl n euraminic a cid ), the most common sialic acid , is a component of the glycocalyx . It binds calcium to macromolecules and cells. Since calcium is an important inter- and intracellular messenger substance , NANA thus forms a messenger substance.

In humans, N- acetylneuraminic acid is the only sialic acid found. This distinguishes it from other mammals, including primates , which in addition to the acetylated form also have a glycolated one, namely N- glycolyl neuraminic acid .

Extraction and presentation

NANA arises from mannosamine through two reactions :

Addition of a pyruvate residue to the C1 atom (product: neuraminic acid)
Acetylation of the amino group

The numbering of α- N -acetylneuraminic acid begins with the carboxy group; with glucose there would be a hydroxyl group at this point.

Individual evidence

↑ Entry on ACETYLNEURAMINIC ACID in the CosIng database of the EU Commission, accessed on May 19, 2020.
↑ ^a ^b ^c Data sheet N-Acetylneuraminic acid from Acros, accessed on December 19, 2019.
↑ ^a ^b Data Sheet N-Acetylneuraminic acid, from at Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
↑ Justin L. Sonnenburg, Tasha K. Altheide, Ajit Varki: A uniquely human consequence of domain-specific functional adaptation in a sialic acid-binding receptor. In: Glycobiology. Vol. 14, No. 4, April 2004, pp. 339-346, PMID 14693915 , doi : 10.1093 / glycob / cwh039 .

[CosIng-1] Entry on ACETYLNEURAMINIC ACID in the CosIng database of the EU Commission, accessed on May 19, 2020.

[acros-2] Data sheet N-Acetylneuraminic acid from Acros, accessed on December 19, 2019.

[Sigma-3] Data Sheet N-Acetylneuraminic acid, from at Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).

[4] Justin L. Sonnenburg, Tasha K. Altheide, Ajit Varki: A uniquely human consequence of domain-specific functional adaptation in a sialic acid-binding receptor. In: Glycobiology. Vol. 14, No. 4, April 2004, pp. 339-346, PMID 14693915 , doi : 10.1093 / glycob / cwh039 .