Sulphoxidation reactions catalysed by the Baeyer-Villiger monooxygenase OTEMO from Pseudomonas putida ATCC 17453

The Baeyer-Villiger monooxygenase OTEMO from Pseudomonas putida ATCC 17453 has been employed as biocatalyst in the asymmetric synthesis of a set of optically active sulphoxides. Several alkyl aryl sulphides are oxidized by this biocatalyst leading to the (S)-sulphoxides. Especially for those substrates containing electron-donating groups in the aromatic ring or in the alkyl moiety, good to high enantiopurities can be obtained. OTEMO is also able to perform the kinetic resolution of racemic sulphoxides, but with low enantioselectivities. Finally, parameters that can affect its biocatalytic properties, such as pH, temperature, organic cosolvents and substrate concentration, have been tested to get a better insight into the biocatalytic potential of this hitherto poorly explored oxidative biocatalyst.

Automated summary

The Baeyer-Villiger monooxygenase OTEMO from Pseudomonas putida ATCC 17453 has been utilized as a biocatalyst for the asymmetric synthesis of optically active sulphoxides. Good to high enantiopurities can be achieved for substrates with electron-donating groups, but low enantioselectivities are observed during kinetic resolution of racemic sulphoxides. Various factors including pH, temperature, organic cosolvents, and substrate concentration have been investigated to determine the biocatalytic potential of OTEMO.