Photoinduced promiscuity of cyclohexanone monooxygenase for the enantioselective synthesis of α-deuterated carbonyl compounds

Abstract

The direct asymmetric synthesis of deuterium compounds has gained increasing attention. Here we report the engineered cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 for the synthesis of chiral α-deuterated carbonyl compounds via enantioselective reductive dehalogenation. The engineered CHMO exhibited good chemoselectivity, stereoselectivity and d-incorporation (up to 92% yield, 98% e.e. and 96% d-incorporation) toward a series of α-halogen carbonyl compounds. This method was also used for the synthesis of deuterated drugs, which demonstrated its promising application in synthetic chemistry.