N-Glycolylneuraminic acid

N-Glycolylneuraminic acid
Names
	IUPAC name 3,5-Dideoxy-5-(glycoloylamino)-d-glycero-β-d-galacto-non-2-ulopyranosonic acid
	Other names GcNeu; NGNA; NeuNGl; Neu5Gc
Identifiers
CAS Number	1113-83-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:62084 ;
ChemSpider	110352 ;
PubChem CID	123802;
UNII	NB446XTC7L ;
	InChI InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1 Key: FDJKUWYYUZCUJX-AJKRCSPLSA-N ; InChI=1/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1 Key: FDJKUWYYUZCUJX-AJKRCSPLBU;
	SMILES C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O;
Properties
Chemical formula	C11H19NO10
Molar mass	325.27 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

N-Glycolylneuraminic acid (Neu5Gc) is a sialic acid molecule found in most non-human mammals. Humans cannot synthesize Neu5Gc because the human gene CMAH is irreversibly mutated, though it is found in other apes. The gene CMAH encodes CMP-N-acetylneuraminic acid hydroxylase, which is the enzyme responsible for CMP-Neu5Gc from CMP-N-acetylneuraminic (CMP-Neu5Ac) acid. This loss of CMAH is estimated to have occurred two to three million years ago, just before the emergence of the genus Homo.

Neu5Gc is closely related to the commonly known N-acetylneuraminic acid (Neu5Ac). Neu5Ac differs by a single oxygen atom that is added by the CMAH enzyme in the cytosol of a cell. In many mammals, both of these molecules are transferred into the Golgi apparatus so that they may be added to many glycoconjugates. However, in humans, Neu5Gc is not present.