Stereoinversion of R-Configured Secondary Alcohols Using a Single Enzymatic Approach

Musa M. Musa*, Ibrahim Karume, Masateru Takahashi, Samir M. Hamdan, Nisar Ullah

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Here, we achieved a single-enzymatic stereoinversion of R-configured alcohols to their corresponding S enantiomers in high percent conversion and high enantioselectivity. A single mutant of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH) oxidized R alcohols to their corresponding ketones under conditions that allow selectivity mistakes and then reduced them under stereoselective conditions to generate the corresponding S-configured alcohols. The success of this stereoinversion relies on controlling the stereoselectivity of the oxidation and the reduction reactions by varying the amounts of acetone and 2-propanol, respectively. Furthermore, the deployment of the TeSADH mutants W110A and W110G led to stereoinversion of enantiopure R alcohols to their S enantiomers in medium to high enantiomeric excess (up to >99% ee). The disclosed approach of single enzymatic stereoinversion presents a biocatalytic alternative to Mitsunobu inversion reaction.

Original languageEnglish (US)
Pages (from-to)10205-10208
Number of pages4
JournalChemistrySelect
Volume3
Issue number36
DOIs
StatePublished - Sep 28 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Alcohol dehydrogenase
  • redox reactions
  • stereoinversion
  • stereoselectivity

ASJC Scopus subject areas

  • Chemistry(all)

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