Enantiospecific (S)-(+)-linalool formation from beta-myrcene by linalool dehydratase-isomerase

Z Naturforsch C J Biosci. Jul-Aug 2011;66(7-8):409-12. doi: 10.1515/znc-2011-7-813.

Abstract

The linalool dehydratase-isomerase from Castellaniella defragrans strain 65Phen catalyzes in the thermodynamically unfavourable direction the hydration of betamyrcene to linalool and further the isomerization to geraniol, the initial steps in anaerobic beta-myrcene biodegradation. We have now investigated the stereochemistry of this reaction. (S)-(+)-Linalool is formed with an enantiomeric excess of at least 95.4%. (R)-(-)-Linalool was not detected. This indicates an introduction of the hydroxy group on the si-face of beta-myrcene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyclic Monoterpenes
  • Biotransformation
  • Catalysis
  • Hydro-Lyases / chemistry
  • Hydro-Lyases / metabolism*
  • Monoterpenes / metabolism*
  • Proteobacteria / enzymology*
  • Stereoisomerism

Substances

  • Acyclic Monoterpenes
  • Monoterpenes
  • beta-myrcene
  • linalool
  • Hydro-Lyases
  • linalool dehydratase-isomerase, Castellaniella defragrans