Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase

Handle URI:
http://hdl.handle.net/10754/621431
Title:
Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase
Authors:
Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir ( 0000-0001-5192-1852 ) ; Musa, Musa M. ( 0000-0001-8191-6077 )
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division
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.
Publisher:
Wiley-Blackwell
Journal:
ChemCatChem
Issue Date:
1-Mar-2016
DOI:
10.1002/cctc.201600160
Type:
Article
ISSN:
1867-3880
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.
Appears in Collections:
Articles; Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorKarume, Ibrahimen
dc.contributor.authorTakahashi, Masateruen
dc.contributor.authorHamdan, Samiren
dc.contributor.authorMusa, Musa M.en
dc.date.accessioned2016-11-03T08:29:09Z-
dc.date.available2016-11-03T08:29:09Z-
dc.date.issued2016-03-01en
dc.identifier.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.en
dc.identifier.issn1867-3880en
dc.identifier.doi10.1002/cctc.201600160en
dc.identifier.urihttp://hdl.handle.net/10754/621431-
dc.description.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.en
dc.description.sponsorshipThe 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.en
dc.publisherWiley-Blackwellen
dc.subjectAlcoholsen
dc.subjectEnantioselectivityen
dc.subjectEnzyme catalysisen
dc.subjectOxidationen
dc.subjectReductionen
dc.titleDeracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenaseen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.identifier.journalChemCatChemen
dc.contributor.institutionChemistry Department; King Fahd University of Petroleum and Minerals; Dhahran 31261 Saudi Arabiaen
kaust.authorTakahashi, Masateruen
kaust.authorHamdan, Samiren
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.