Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer–Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv

Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer–Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer–Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably.

Graphical abstractIn contrast to previously reported Baeyer–Villiger monooxygenases, kinetic resolution processes of fused cyclobutanones are performed by engineered Escherichia coli expressing an enzyme from Mycobacterium tuberculosis.Figure optionsDownload full-size imageDownload as PowerPoint slide