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Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water
Author(s) -
Köninger Katharina,
Gómez Baraibar Álvaro,
Mügge Carolin,
Paul Caroline E.,
Hollmann Frank,
Nowaczyk Marc M.,
Kourist Robert
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601200
Subject(s) - enantioselective synthesis , cyanobacteria , yield (engineering) , chemistry , catalysis , biocatalysis , combinatorial chemistry , recombinant dna , enantiomeric excess , stereochemistry , organic chemistry , biochemistry , materials science , reaction mechanism , bacteria , biology , gene , metallurgy , genetics
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.