Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells

Appl Environ Microbiol. 2001 Jun;67(6):2829-32. doi: 10.1128/AEM.67.6.2829-2832.2001.

Abstract

The toluene-degrading strain Rhodococcus opacus PWD4 was found to hydroxylate D-limonene exclusively in the 6-position, yielding enantiomerically pure (+) trans-carveol and traces of (+) carvone. This biotransformation was studied using cells cultivated in chemostat culture with toluene as a carbon and energy source. The maximal specific activity of (+) trans-carveol formation was 14.7 U (g of cells [dry weight])(-1), and the final yield was 94 to 97%. Toluene was found to be a strong competitive inhibitor of the D-limonene conversion. Glucose-grown cells did not form any trans-carveol from D-limonene. These results suggest that one of the enzymes involved in toluene degradation is responsible for this allylic monohydroxylation. Another toluene degrader (Rhodococcus globerulus PWD8) had a lower specific activity but was found to oxidize most of the formed trans-carveol to (+) carvone, allowing for the biocatalytic production of this flavor compound.

MeSH terms

  • Biotransformation
  • Culture Media
  • Cyclohexane Monoterpenes
  • Cyclohexenes
  • Flavoring Agents / metabolism*
  • Glucose / metabolism
  • Isomerism
  • Limonene
  • Monoterpenes*
  • Rhodococcus / growth & development*
  • Rhodococcus / metabolism*
  • Species Specificity
  • Terpenes / metabolism*
  • Toluene / metabolism*

Substances

  • Culture Media
  • Cyclohexane Monoterpenes
  • Cyclohexenes
  • Flavoring Agents
  • Monoterpenes
  • Terpenes
  • Toluene
  • carvone
  • carveol
  • Limonene
  • Glucose