N-Glycolylneuraminic acid

N-Glycolylneuraminic acid
Names
	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.^[1]^[2] The gene CMAH encodes CMP-N-acetylneuraminic acid hydroxylase, which is the enzyme responsible for CMP-Neu5Gc from CMP-N-acetylneuraminic (CMP-Neu5Ac) acid.^[3] This loss of CMAH is estimated to have occurred two to three million years ago, just before the emergence of the genus Homo.^[4]

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.^[4]^[5]

^
Chou, Hsun-Hua; Takematsu, Hiromu; Diaz, Sandra; Iber, Jane; Nickerson, Elizabeth; Wright, Kerry L.; Muchmore, Elaine A.; Nelson, David L.; Warren, Stephen T.; Varki, Ajit (1998). "A mutation in human CMP-sialic acid hydroxylase occurred after the Homo-Pan divergence". Proceedings of the National Academy of Sciences. 95 (20): 11751–6. Bibcode:1998PNAS...9511751C. doi:10.1073/pnas.95.20.11751. JSTOR 49259. PMC 21712. PMID 9751737.
- "Difference Between Humans and Apes Linked to a Missing Oxygen Atom". UCSD Health Sciences (Press release). September 25, 1998.
^ Varki, Ajit (2001). "Loss of N-glycolylneuraminic acid in humans: Mechanisms, consequences, and implications for hominid evolution". American Journal of Physical Anthropology. 116 (Suppl 33): 54–69. doi:10.1002/ajpa.10018. PMC 7159735. PMID 11786991.
^ Ghaderi, Darius; Taylor, Rachel E; Padler-Karavani, Vered; Diaz, Sandra; Varki, Ajit (2010). "Implications of the presence of N-glycolylneuraminic acid in recombinant therapeutic glycoproteins". Nature Biotechnology. 28 (8): 863–7. doi:10.1038/nbt.1651. PMC 3077421. PMID 20657583.
^ ^a ^b Varki, Ajit (2010). "Uniquely human evolution of sialic acid genetics and biology". Proceedings of the National Academy of Sciences. 107 (Suppl 2): 8939–46. Bibcode:2010PNAS..107.8939V. doi:10.1073/pnas.0914634107. PMC 3024026. PMID 20445087.
^ Dankwa, Selasi (4 April 2016). "Ancient human sialic acid variant restricts an emerging zoonotic malaria parasite". Nature Communications. 7: 11187. Bibcode:2016NatCo...711187D. doi:10.1038/ncomms11187. PMC 4822025. PMID 27041489.

[1] Chou, Hsun-Hua; Takematsu, Hiromu; Diaz, Sandra; Iber, Jane; Nickerson, Elizabeth; Wright, Kerry L.; Muchmore, Elaine A.; Nelson, David L.; Warren, Stephen T.; Varki, Ajit (1998). "A mutation in human CMP-sialic acid hydroxylase occurred after the Homo-Pan divergence". Proceedings of the National Academy of Sciences. 95 (20): 11751–6. Bibcode:1998PNAS...9511751C. doi:10.1073/pnas.95.20.11751. JSTOR 49259. PMC 21712. PMID 9751737.
"Difference Between Humans and Apes Linked to a Missing Oxygen Atom". UCSD Health Sciences (Press release). September 25, 1998.

[2] "Difference Between Humans and Apes Linked to a Missing Oxygen Atom". UCSD Health Sciences (Press release). September 25, 1998.

[2] Varki, Ajit (2001). "Loss of N-glycolylneuraminic acid in humans: Mechanisms, consequences, and implications for hominid evolution". American Journal of Physical Anthropology. 116 (Suppl 33): 54–69. doi:10.1002/ajpa.10018. PMC 7159735. PMID 11786991.

[Implications-3] Ghaderi, Darius; Taylor, Rachel E; Padler-Karavani, Vered; Diaz, Sandra; Varki, Ajit (2010). "Implications of the presence of N-glycolylneuraminic acid in recombinant therapeutic glycoproteins". Nature Biotechnology. 28 (8): 863–7. doi:10.1038/nbt.1651. PMC 3077421. PMID 20657583.

[Uniquely_Human-4] Varki, Ajit (2010). "Uniquely human evolution of sialic acid genetics and biology". Proceedings of the National Academy of Sciences. 107 (Suppl 2): 8939–46. Bibcode:2010PNAS..107.8939V. doi:10.1073/pnas.0914634107. PMC 3024026. PMID 20445087.

[5] Dankwa, Selasi (4 April 2016). "Ancient human sialic acid variant restricts an emerging zoonotic malaria parasite". Nature Communications. 7: 11187. Bibcode:2016NatCo...711187D. doi:10.1038/ncomms11187. PMC 4822025. PMID 27041489.

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