Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase
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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.
CitationKarume 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.
SponsorsThe 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.