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dc.contributor.authorBsharat, Odey
dc.contributor.authorMusa, Musa M.
dc.contributor.authorVieille, Claire
dc.contributor.authorOladepo, Sulayman
dc.contributor.authorTakahashi, Masateru
dc.contributor.authorHamdan, Samir
dc.date.accessioned2017-06-14T12:04:28Z
dc.date.available2017-06-14T12:04:28Z
dc.date.issued2017-04-06
dc.identifier.citationBsharat O, Musa MM, Vieille C, Oladepo SA, Takahashi M, et al. (2017) Asymmetric Reduction of Substituted 2-Tetralones by Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase. ChemCatChem 9: 1487–1493. Available: http://dx.doi.org/10.1002/cctc.201601618.
dc.identifier.issn1867-3880
dc.identifier.doi10.1002/cctc.201601618
dc.identifier.urihttp://hdl.handle.net/10754/624996
dc.description.abstractKetones bearing two bulky substituents, named bulky-bulky ketones, were successfully reduced to their corresponding optically enriched alcohols by using various mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). Substituted 2-tetralones, in particular, were reduced to 2-tetralols with high conversion and high enantioselectivity. The pharmacological importance of substituted 2-tetralols as key drug-building blocks makes our biocatalytic reduction method a highly essential tool. We showed that changing the position of the substituent on the aromatic ring of 2-tetralones impacts their binding affinity and the reaction maximum catalytic rate. Docking studies with several TeSADH mutants explain how the position of the substituent on the tetralone influences the binding orientation of substituted 2-tetralones and their reaction stereoselectivity.
dc.description.sponsorshipThe authors acknowledge the support provided by the Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) for funding this work through project number IN151032.
dc.publisherWiley
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/cctc.201601618/full
dc.subjectasymmetric catalysis
dc.subjectenzyme catalysis
dc.subjectketones
dc.subjectmutagenesis
dc.subjectreduction
dc.titleAsymmetric Reduction of Substituted 2-Tetralones by Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentBioscience Program
dc.identifier.journalChemCatChem
dc.contributor.institutionKing Fahd University of Petroleum and Minerals; Chemistry Department; 31261 Dhahran SAUDI ARABIA
dc.contributor.institutionKing Fahd University of Petroleum and Minerals; Chemistry; Department of Chemistry Building #4 31261 Dhahran SAUDI ARABIA
dc.contributor.institutionMichigan State University; Department of Microbiology and Molecular Genetics; 48824 East Lansing UNITED STATES
kaust.personTakahashi, Masateru
kaust.personHamdan, Samir
dc.date.published-online2017-04-06
dc.date.published-print2017-04-21


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