Asymmetric Sulfoxidation Catalyzed by a Vanadium-Containing Bromoperoxidase.
A vanadium-containing bromoperoxidase (VBrPO) from the alga Corallina officinalis has been shown to catalyze the stereoselective oxidation of some aromatic bicyclic sulfides to the corresponding (S)-sulfoxides in high (up to 91%) ee. Hydrogen peroxide was found to have a large effect on the catalyzed reaction, most likely due to an inhibition of VBrPO. High optical and chemical yields were found to be favored by a continuous slow addition of hydrogen peroxide to keep a low excess. The reaction gives no overoxidation to sulfone, and its stereochemistry is the opposite as compared to that previously found with the heme-containing chloroperoxidase (CPO) from Caldariomyces fumago.
Andersson
Malin
M
Department of Chemistry, University of Göteborg, S-41296 Göteborg, Sweden, and Department of Biological Sciences, University of Exeter, Exeter, EX4 4QD, U.K.
Willetts
Andrew
A
Allenmark
Stig
S