Direct electrochemical regeneration of monooxygenase subunits for biocatalytic asymmetric epoxidation.
We report the first example of direct electrochemical regeneration of a flavin-dependent monooxygenase for asymmetric epoxidation catalysis. It is shown that electrochemical regeneration of the oxygenase subunit of the multicomponent styrene monooxygenase is sufficient to perform enantiospecific S-epoxidation of various styrene derivatives. Kinetic bottlenecks of the novel electroenzymatic reaction are identified. This work opens up new alternatives for asymmetric oxyfunctionalization catalysis.
Hollmann
Frank
F
Institute for Biotechnology, Swiss Federal Institute of Technology, Zurich, Switzerland, BASF Aktiengesellschaft, Ludwigshafen, Germany.
Hofstetter
Karin
K
Habicher
Tilo
T
Hauer
Bernhard
B
Schmid
Andreas
A
D002374:Catalase / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004563:Electrochemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D038181:FMN Reductase / Q000737:chemistry*; D005182:Flavin-Adenine Dinucleotide / Q000031:analogs & derivatives* / Q000737:chemistry; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology; D013343:Styrenes / Q000737:chemistry
D004852:Epoxy Compounds; D013343:Styrenes; D005182:Flavin-Adenine Dinucleotide; C058805:1,5-dihydro-FAD; D002374:Catalase; D010105:Oxygenases; C026721:styrene monooxygenase; D038181:FMN Reductase; C009068:propylene oxide