Chemical behaviour of cytidine 5'-monophospho-N-acetyl-beta-D-neuraminic acid under neutral and alkaline conditions

Eur J Biochem. 1984 Apr 2;140(1):203-8. doi: 10.1111/j.1432-1033.1984.tb08087.x.

Abstract

The chemical behaviour of CMP-N-acetylneuraminic acid under neutral and different alkaline conditions has been investigated. The products formed were isolated by ion-exchange chromatography and gel filtration and analysed by colorimetric methods, thin-layer chromatography, combined gas-liquid chromatography/mass spectrometry and/or 360-MHz 1H-NMR spectroscopy. A maximum stability of CMP-N-acetylneuraminic acid was observed at pH8-11. In the tested pH range of 6-13, CMP and N-acetylneuraminic acid were formed in variable amounts as decomposition products. 2-Deoxy-2,3-dehydro-N-acetylneuraminic acid was produced at pH greater than 7; the amount of this substance increased with increasing pH. In anhydrous triethylamine its yield was 50%. A new neuraminic acid derivative, N-acetyl-beta-D-neuraminic acid 2-phosphate, could be isolated from the mixture of alkaline decomposition products of CMP-N-acetylneuraminic acid. The yield of this compound was maximum 22% in anhydrous triethylamine. Because 2-deoxy-2,3-dehydro-N-acetylneuraminic acid was formed under simulated physiological conditions, it is assumed that this compound, which occurs in tissues and fluids of man and animals, is derived from CMP-N-acetylneuraminic acid non-enzymically also under conditions in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Chromatography, Thin Layer
  • Colorimetry
  • Cytidine Monophosphate N-Acetylneuraminic Acid*
  • Gas Chromatography-Mass Spectrometry
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Sialic Acids*
  • Spectrophotometry, Ultraviolet

Substances

  • Sialic Acids
  • Cytidine Monophosphate N-Acetylneuraminic Acid