Stereoselective reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae

Biotechnol Lett. 2003 Jun;25(12):987-92. doi: 10.1023/a:1024057425226.

Abstract

A comparative study of two modifications of enzymic reduction of ethyl N-[2-[4-[(2-oxo-cyclohexyl)methyl]phenoxy]ethyl]carbamate (1), an insect juvenile hormone bioanalog, was performed using Saccharomyces cerevisiae in two bioreactors of different size, 250-ml shake-flask and 1-l fermenter. The two major products of this reduction were obtained in 45-49% (w/w) yields but with > 99% enantiomeric purity. Their absolute configurations were assigned as ethyl (1S,2S)-N-[2-[4-[(2-hydroxycyclohexyl)methyl]phenoxy]ethyl]carbamate (2a) and ethyl (1R,2S)-N-[2-[4-[(2-hydroxycyclohexyl)methyl]phenoxy]ethyl]carbamate (3a).

Publication types

  • Comparative Study
  • Evaluation Study
  • Research Support, Non-U.S. Gov't
  • Validation Study

MeSH terms

  • Alcohols / metabolism*
  • Bioreactors*
  • Carbamates / metabolism*
  • Cyclohexanones / metabolism*
  • Oxidation-Reduction
  • Pilot Projects
  • Quality Control
  • Saccharomyces cerevisiae / chemistry
  • Saccharomyces cerevisiae / classification
  • Saccharomyces cerevisiae / enzymology
  • Saccharomyces cerevisiae / metabolism*
  • Species Specificity
  • Stereoisomerism

Substances

  • Alcohols
  • Carbamates
  • Cyclohexanones