Enzymatic Production of Both Enantiomers of Rhododendrol

Musa M. Musa

Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Kingdom of Saudi Arabia

Corresponding author: Fax: +966 138604277; Tel: +966 138607343; E-mail: musam@kfupm.edu.sa

Abstract

An asymmetric synthetic approach to produce (R)- and (S)-rhododendrol is described. W110A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (W110A TeSADH), an (S)-specific mutant of TeSADH, is used in this approach. The enantioselective reduction of 4-(4'-hydroxyphenyl)-2-butanone catalyzed by W110A TeSADH yielded (S)-rhododendrol, the Prelog product. The anti-Prelog product, (R)-rhododendrol, is produced from (rac)-rhododendrol through enantiospecific kinetic resolution catalyzed by W110A TeSADH.

Keywords

Alcohol dehydrogenases, Asymmetric reduction, Biotransformations, Kinetic resolution, Redox reactions, Rhododendrol.

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