Applications of Baeyer-Villiger Monooxygenases in Organic Synthesis

Veronique      Alphand; Roland      Wohlgemuth

doi:10.2174/138527210792927519

Abstract

The knowledge about these Baeyer-Villiger monooxygenases has grown tremendously since the first discovery and fundamental progress in the understanding of structure, function, substrate specificities and other enzyme properties has been facilitated by the development of recombinant biocatalysts. Nature uses these biocatalysts in aerobic biodegradation pathways of cyclic and acyclic ketones and in the biosynthetic pathways of natural products. The excellent performance of Baeyer-Villiger monooxygenases in nature for the catalysis of Baeyer-Villiger oxidations with high chemo-, regio- and enantioselectivity is a role model for sustainable catalytic Baeyer- Villiger oxidations in organic synthesis. A broad range of biocatalytic conversions of cyclic ketones to lactones, linear ketones to esters, sulfoxidations and other oxidations is described. Applications in dynamic kinetic resolution as well as process and scale-up issues have been important in making this reaction platform attractive to industrial scale Baeyer-Villiger oxidations. New discoveries of Baeyer- Villiger monooxygenases in biosynthesis are promising for highly selective oxidations.

Keywords: Biocatalytic Baeyer-Villiger Oxidation, Asymmetric Synthesis, Monooxygenases, Biocatalytic Asymmetric Oxidation, Lactones, Esters, Sulfoxides, Desymmetrization, Kinetic Resolution, Large-Scale Processes, Oxidation, Synthesis, Biocatalytic, Resolution, Large-Scale, BVMOs, FAD, FMN, CHMOAcineto, CHMOs, lactone, E value, ATCC 17453, bicyloketone, NCIMB, P.putida, CDPMO, CPDMO, HAPMO, CHMO, MeKA, kcat/KM, CCT 3119, AKMO, PAMO, Diels-Alder reactions, Xanthobacter sp, DKR process, HPLC, Mithramycin