Open AccessElectroenzymatic Synthesis of Chiral Sulfoxides
Author(s) -
Kohlmann C.,
Lütz S.
Publication year - 2006
Publication title -
engineering in life sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.547
H-Index - 57
eISSN - 1618-2863
pISSN - 1618-0240
DOI - 10.1002/elsc.200620907
Subject(s) - hydrogen peroxide , chemistry , benzene , electrochemistry , enzyme , sulfide , enantiomer , organic chemistry , hydrogen sulfide , enantiomeric excess , redox , catalysis , sulfur , enantioselective synthesis , electrode
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.