Biocatalytical asymmetric sulfoxidation by identifying cytochrome P450 from Parvibaculum lavamentivorans DS-1

Cytochrome P450 monooxygenases (P450s) catalyzed asymmetric sulfoxidation represents a green route for the synthesis of valuable enantiopure sulfoxides, which are potentially interesting synthons in synthetic and pharmaceutical chemistry. Here the potential P450 and redox partner genes from Parvibaculum lavamentivorans DS-1 are screened and co-expressed in Escherichia coli host to construct twenty recombinant P450 strains. By testing the whole-cell biooxidation of thioanisole, P450(PL2) (CYP278A4) and P450(PL7) (CYP108G3) are identified with excellent S enantioselectivity while P450(PL1) (CYP111B1) and P450(PL9) (CYP153A26) exhibit the complementary R enantioselectivity. Asymmetric sulfoxidation of sulfides 1a-1m is further investigated using the recombinant E. coli strain P450(PL2)-2 based on the optimal conditions, producing the corresponding enantioenriched sulfoxides with up to 82% isolated yield and 99% ee.