Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase

Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir; Musa, Musa M.

Type

Article

Authors

Karume, Ibrahim
Takahashi, Masateru
Hamdan, Samir

Musa, Musa M.

KAUST Department

Biological and Environmental Sciences and Engineering (BESE) Division
Bioscience Program

Date

2016-03-01

Online Publication Date

2016-03-01

Print Publication Date

2016-04-20

Permanent link to this record

http://hdl.handle.net/10754/621431

Metadata

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Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. We developed a single-enzyme-mediated two-step approach for deracemization of secondary alcohols. A single mutant of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase enables the nonstereoselective oxidation of racemic alcohols to ketones, followed by a stereoselective reduction process. Varying the amounts of acetone and 2-propanol cosubstrates controls the stereoselectivities of the consecutive oxidation and reduction reactions, respectively. We used one enzyme to accomplish the deracemization of secondary alcohols with up to >99% ee and >99.5% recovery in one pot and without the need to isolate the prochiral ketone intermediate.

Citation

Karume I, Takahashi M, Hamdan SM, Musa MM (2016) Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase. ChemCatChem 8: 1459–1463. Available: http://dx.doi.org/10.1002/cctc.201600160.

Sponsors

The authors acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science and Technology Unit at King Fahd University of Petroleum and Minerals (KFUPM), for funding this work through project No. 11-BIO1666-04, as part of the National Science, Technology and Innovation Plan. The authors thank Prof. Claire Vieille, from the Department of Microbiology and Molecular Genetics at Michigan State University, for providing the plasmids of TeSADH and W110A TeSADH. The authors also thank Prof. Omar M. Yaghi for helpful suggestions.