Stereoselective reduction of 2-substituted cyclohexanones by Saccharo- myces cerevisiae

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).

DOI: 10.1023/A:1024057425226

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Cite this paper

@article{Zarevck2003StereoselectiveRO, title={Stereoselective reduction of 2-substituted cyclohexanones by Saccharo- myces cerevisiae}, author={Marie Zarev{\'u}ck{\'a} and Pavla Sochůrkov{\'a} and Zdeněk Wimmer and David {\vS}aman}, journal={Biotechnology Letters}, year={2003}, volume={25}, pages={987-992} }