Electroenzymatic synthesis of chiral sulfoxides

Abstract

Chloroperoxidase (CPO) from Caldariomyces fumago (E.C.1.11.1.10) is able to enantioselectively oxidize various sulfides to the corresponding (R)-enantiomer of the sulfoxides. For these oxidations the enzyme requires an oxidant. Most commonly, tert-butyl hydroperoxide (TBHP) and hydrogen peroxide are used. As it is known that these oxidants inactivate the enzyme, the enzymatic reaction was combined with the electrochemical in situ generation of hydrogen peroxide. As substrates for this combination of an enzymatic and an electrochemical reaction methyl p-tolyl sulfide, 1-methoxy-4-(methylthio)benzene and N-MOC-L-methionine methyl ester were used to carry out batch experiments. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.