Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water

Katharina Köninger, Álvaro Gómez Baraibar, Carolin Mügge, Caroline E Paul, Frank Hollmann, Marc M Nowaczyk, Robert Kourist

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A recombinant enoate reductase was expressed in cyanobacteria and used for the light-catalyzed, enantioselective reduction of C=C bonds. The coupling of oxidoreductases to natural photosynthesis allows asymmetric syntheses fueled by the oxidation of water. Bypassing the addition of sacrificial cosubstrates as electron donors significantly improves the atom efficiency and avoids the formation of undesired side products. Crucial factors for product formation are the availability of NADPH and the amount of active enzyme in the cells. The efficiency of the reaction is comparable to typical whole-cell biotransformations in E. coli. Under optimized conditions, a solution of 100 mg prochiral 2-methylmaleimide was reduced to optically pure 2-methylsuccinimide (99 % ee, 80 % yield of isolated product). High product yields and excellent optical purities demonstrate the synthetic usefulness of light-catalyzed whole-cell biotransformations using recombinant cyanobacteria.

Original languageEnglish
Pages (from-to)5582-5
Number of pages4
JournalAngewandte Chemie / International Edition
Volume55
Issue number18
DOIs
Publication statusPublished - 25 Apr 2016
Externally publishedYes

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Keywords

  • Journal Article

Fields of Expertise

  • Human- & Biotechnology

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