The stereochemical course of tricho-acorenol biosynthesis

Org Biomol Chem. 2013 Nov 21;11(43):7447-50. doi: 10.1039/c3ob41755g.

Abstract

The biosynthesis of tricho-acorenol in Trichoderma harzianum was investigated by feeding stereospecifically deuterated mevalonolactone isotopomers, followed by a detailed GC/MS analysis of the incorporation of labelling. The results establish a highly stereospecific hydride migration and antarafacial attack of water in the terminal step towards tricho-acorenol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Gas Chromatography-Mass Spectrometry
  • Mevalonic Acid / analogs & derivatives
  • Mevalonic Acid / metabolism
  • Molecular Structure
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / metabolism*
  • Stereoisomerism
  • Trichoderma / metabolism*

Substances

  • Sesquiterpenes
  • mevalonolactone
  • Mevalonic Acid