Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus
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Type
ArticleKAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionBioscience Program
Environmental Science and Engineering Program
King Abdullah University of Science and Technology; Biological and Environmental Science and Engineering; SAUDI ARABIA
Laboratory of DNA Replication and Recombination
Date
2020-07-16Online Publication Date
2020-07-16Print Publication Date
2020-08-16Embargo End Date
2021-07-03Submitted Date
2020-05-22Permanent link to this record
http://hdl.handle.net/10754/664114
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We developed a one-pot two-step deracemization approach for alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase ( Te SADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of Te SADH with poor and good stereoselectivities, respectively. More specifically, W110G Te SADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V Te SADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure ( S )-configured alcohols in up to >99% enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G Te SADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G Te SADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of ( R )-configured alcohols, and ( S )-configured alcohols with up to >99% enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.Citation
Nafiu, S. A., Takahashi, M., Takahashi, E., Hamdan, S. M., & Musa, M. M. (2020). Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus. European Journal of Organic Chemistry. doi:10.1002/ejoc.202000728Sponsors
The 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 DF191007. The authors also thank Prof. Claire Vieille, from the Department of Microbiology and Molecular Genetics as well as Biochemistry and Molecular Biology at Michigan State University, for providing the plasmids of TeSADH.Publisher
WileyAdditional Links
http://doi.wiley.com/10.1002/ejoc.202000728ae974a485f413a2113503eed53cd6c53
10.1002/ejoc.202000728