Stereochemistry of the enzymatic reduction of 
2-(4-Methoxybenzyl)-1-cyclohaxanone by means of Solanum aviculare cells in vitro

Vanek, T.; Wimmer, Z.; Macek, T.; Saman, D.; Svatoš, Aleš; Romanuk, M.

doi:10.3109/10242428908992036

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Stereochemistry of the enzymatic reduction of 2-(4-Methoxybenzyl)-1-cyclohaxanone by means of Solanum aviculare cells in vitro

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Vanek, T., Wimmer, Z., Macek, T., Saman, D., Svatoš, A., & Romanuk, M. (1989). Stereochemistry of the enzymatic reduction of 2-(4-Methoxybenzyl)-1-cyclohaxanone by means of Solanum aviculare cells in vitro. Biocatalysis, 2(4), 265-272. doi:10.3109/10242428908992036.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0012-B433-0

Abstract

During the investigation of chemical properties of the dicyclic system of insect juvenile hormone analogues, biotransformation of 2-(4-methoxybenzyl)-1-cyclohexanone (1) by plant cell cultures was studied. Among other components, the cis-(1S, 2S)- and cis-(1R, 2R)-2-(4-methoxybenzyl)-1-cyclohexanol enantiomers 2a and 2b were found in the reaction mixture. Higher stereoselectivity of the biotransformation was observed for trans-(1S, 2R)-enantiomer 3a formation, which occurred in at least 60% of calculated enantiomeric excess.