Identification of the stereoisomeric configurations of methylcitric acid produced by si-citrate synthase and methylcitrate synthase using capillary gas chromatography-mass spectrometry

J Inherit Metab Dis. 1994;17(6):738-47. doi: 10.1007/BF00712017.

Abstract

The absolute separation of the four stereoisomeric configurations of methylcitric acid can be achieved on a nonchiral stationary phase SE30 capillary column using the corresponding O-acetylated (tri-(-)-2-butyl ester derivatives. Identification of the separated isomers was done using methylcitric acid produced by si-citrate synthase and methylcitrate synthase of Candida lipolitica. si-Citrate synthase produces the (2S,3S)-, (2S,3R)- and a small amount of the (2R,3S)-isomers. Methylcitrate synthase produces the (2R,3S)-isomer, indicating that this enzyme is more stereospecific than the animal citrate synthase enzyme. The (2R,3R)-isomer may act as an inhibitor of aconitase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Citrate (si)-Synthase / metabolism*
  • Citrates / biosynthesis
  • Citrates / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Stereoisomerism

Substances

  • Citrates
  • 2-methylcitric acid
  • Citrate (si)-Synthase
  • methylcitrate synthase