Stereochemical congruence of Baeyer–Villigerases

Abstract

The enantiomeric bicyclic ketones 1, 3 and the tricyclic ketone 5 undergo stereochemically congruent Baeyer-Villiger oxidations with CHMO from Acinetobacter sp., CPMO from Pseudomonas sp. as well as 2,5-DKCMO, 3,6-DKCMO and MO2 from P. putida; in every case the tricyclic ketone 5 is transformed with > 96% ee. N-terminal sequences for the FAD/NADPH linked enzymes from Acinetobacter sp., Pseudomonas sp. and a novel CHMO from R. coprophilus have high homology with each other but no homology with the FMN/NADH linked enzymes; 2,5-DKCMO and 3,6-DKCMO.