Biotechnology Letters, Vol.25, No.12, 987-992, 2003
Stereoselective reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae
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).
Keywords:bioreactor;diastereoisomer;enantiomer;enzymic reduction;Saccharomyces cerevisiae;2-substituted cyclohexanone