N -Glycolyl neuraminic acid

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Structural formula
Structural formula of N-glycolyl neuraminic acid
β- anomer of N- glycolyl neuraminic acid
General
Surname N -Glycolyl neuraminic acid
other names

New5Gc

Molecular formula C 11 H 19 NO 10
Brief description

colorless solid

External identifiers / databases
CAS number 1113-83-3
PubChem 123802
ChemSpider 110352
Wikidata Q309533
properties
Molar mass 325.27 g mol −1
safety instructions
GHS labeling of hazardous substances
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 -Glycolyl neuraminic acid , also known as Neu5Gc , belongs to the class of sialic acids .

Neu5Gc is a common sialic acid in animal organisms. In contrast, Neu5Gc is absent in the human organism. Only N- acetylneuraminic acid occurs in humans , since the enzyme CMP-Neu5Ac-hydroxylase, which catalyzes the formation of N -glycolylneuraminic acid from N -acetylneuraminic acid , is not functional in humans. The gene coding for the corresponding enzyme (CMP-Neu5Ac hydroxylase = CMAH ) encoding , in man by a mutation function. In contrast, chimpanzees , for example, have the ability to synthesize Neu5Gc - in the brain, among other things. The gene coding for CMAH is located on chromosome 6 gene locus p21.32.

A research team at the University of California, San Diego School of Medicine, led by Ajit Varki, identified a new mechanism in 2014 how consumption of Neu5Gc from external sources such as red meat and dairy products could increase the risk of cancerous tumors . On the other hand, it was observed in 2019 that genetically modified mice without the ability to produce Neu5Gc have an increased risk of developing cardiovascular diseases, and the damaging effect of Neu5Gc from red meat is more the result of human antibody formation against Neu5Gc. The lost ability to produce endogenous Neu5Gc could thus be a cause of the more frequent occurrence of cardiovascular diseases in humans than in animals .

Individual evidence

  1. ↑ a b Data sheet N-Glycolylneuraminic acid from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
  2. ↑ M. von Elstermann: Alternative ways of an endogenous biosynthesis of N-glycolyl neuraminic acid in human breast cancer cells. Dissertation, University of Cologne, 2006. urn : nbn: de: hbz: 38-20747
  3. ^ R. Vaas: Future of Neuroscience. Lexicon of Neuroscience.
  4. ↑ NCBI: CMAH cytidine monophosphate-N-acetylneuraminic acid hydroxylase (CMP-N-acetylneuraminate monooxygenase) pseudogene (Homo sapiens).
  5. ↑ Annie N. Samraj, Oliver MT Pearce, Heinz Läubli, Alyssa N. Crittenden, Anne K. Bergfeld, Kalyan Banda, Christopher J. Gregg, Andrea E. Bingman, Patrick Secrest, Sandra L. Diaz, Nissi M. Varki, and Ajit Varki: A red meat-derived glycan promotes inflammation and cancer progression , PNAS , Jan 13, 2015, 112 (2) 542-547; doi: 10.1073 / pnas.1417508112
  6. ↑ Kawanishi et al .: Human species-specific loss of CMP-N-acetylneuraminic acid hydroxylase enhances atherosclerosis via intrinsic and extrinsic mechanisms , PNAS , August 6, 2019, 116 (32) 16036-16045, doi: 10.1073 / pnas.1902902116 .

literature

  • Hedlund, M. et al . (2007): N-glycolylneuraminic acid deficiency in mice: implications for human biology and evolution , in: Mol Cell Biol 27 (12), pp. 4340-4346; PMID 17420276 .

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