title: Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water.
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.
authors.affiliation: Junior Research Group for Microbial Biotechnology, Ruhr-Universität Bochum, 44780, Bochum, Germany.
authors.forename: Katharina
authors.identifier: 0000-0002-7287-9005
authors.initials: K
authors.lastname: Köninger
authors.affiliation: Junior Research Group for Microbial Biotechnology, Ruhr-Universität Bochum, 44780, Bochum, Germany.
authors.forename: Álvaro
authors.initials: Á
authors.lastname: Gómez Baraibar
authors.affiliation: Junior Research Group for Microbial Biotechnology, Ruhr-Universität Bochum, 44780, Bochum, Germany.
authors.forename: Carolin
authors.identifier: 0000-0002-8065-173X
authors.initials: C
authors.lastname: Mügge
authors.affiliation: Department of Biotechnology, Delft University of Technology, The Netherlands.
authors.forename: Caroline E
authors.initials: CE
authors.lastname: Paul
authors.affiliation: Department of Biotechnology, Delft University of Technology, The Netherlands.
authors.forename: Frank
authors.identifier: 0000-0003-4821-756X
authors.initials: F
authors.lastname: Hollmann
authors.affiliation: Chair of Plant Biochemistry, Ruhr-Universität Bochum, Germany.
authors.forename: Marc M
authors.identifier: 0000-0002-9269-0672
authors.initials: MM
authors.lastname: Nowaczyk
authors.affiliation: Junior Research Group for Microbial Biotechnology, Ruhr-Universität Bochum, 44780, Bochum, Germany. Robert.Kourist@rub.de.
authors.forename: Robert
authors.identifier: 0000-0002-2853-3525
authors.initials: R
authors.lastname: Kourist
mesh_terms: D055162:Biocatalysis; D001711:Biotransformation; D000458:Cyanobacteria / Q000378:metabolism*; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000737:chemistry / Q000378:metabolism*; D011994:Recombinant Proteins / Q000737:chemistry / Q000378:metabolism; D014867:Water / Q000737:chemistry / Q000378:metabolism*
chemical_list: D011994:Recombinant Proteins; D014867:Water; D010088:Oxidoreductases
keywords: biotechnology; enzyme catalysis; photocatalysis; photosynthesis; reduction