Stereospecificity of the (Z)-9 desaturase that converts (E)-11-tetradecenoic acid into (Z,E)-9,11-tetradecadienoic acid in the biosynthesis of Spodoptera littoralis sex pheromone

Insect Biochem Mol Biol. 2001 Jun 22;31(8):799-803. doi: 10.1016/s0965-1748(00)00185-5.

Abstract

Moth pheromone glands contain desaturases that catalyze the formation of conjugated dienoic fatty acids. In this article we present the first stereochemical study on one of these enzymes, namely the Delta(9) desaturase of (E)-11-tetradecenoic acid, using the moth Spodoptera littoralis as a biological model and enantiopure deuterated probes derived from tridecanoic acid. Gas chromatography coupled to mass spectrometry analysis of methanolyzed lipidic extracts from glands incubated with each individual probe showed that in the transformation of (E)-11-tetradecenoic acid into (Z,E)-9,11-tetradecadienoic acid both pro-(R) hydrogen atoms at C9 and C10 are removed from the substrate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fatty Acid Desaturases / metabolism*
  • Fatty Acids, Monounsaturated / metabolism*
  • Fatty Acids, Unsaturated / metabolism*
  • Molecular Conformation
  • Sex Attractants / biosynthesis*
  • Spodoptera / metabolism
  • Stearoyl-CoA Desaturase

Substances

  • 11-tetradecenoic acid
  • 9,11-tetradecadienoic acid
  • Fatty Acids, Monounsaturated
  • Fatty Acids, Unsaturated
  • Sex Attractants
  • Fatty Acid Desaturases
  • Stearoyl-CoA Desaturase
  • delta-9 fatty acid desaturase