Asymmetric Sulfoxidation Catalyzed by a Vanadium-Containing Bromoperoxidase
- 1 November 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (24) , 8455-8458
- https://doi.org/10.1021/jo9712456
Abstract
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.Keywords
This publication has 18 references indexed in Scilit:
- Inhibition and inactivation of vanadium bromoperoxidase by the substrate hydrogen peroxide and further mechanistic studiesBiochemistry, 1995
- Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study.Journal of the American Chemical Society, 1995
- Purification, crystallisation and preliminary X‐ray analysis of the vanadium‐dependent haloperoxidase from Corallina officinalisFEBS Letters, 1995
- Marine haloperoxidasesChemical Reviews, 1993
- Enol oxalacetic acid exists in the Z form in the crystalline state and in solutionThe Journal of Organic Chemistry, 1992
- Mechanism of dioxygen formation catalyzed by vanadium bromoperoxidase from Macrocystis pyrifera and Fucus distichus: steady state kinetic analysis and comparison to the mechanism of V-BrPO from Ascophyllum nodosumBiochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1991
- Enantioselective oxidations of sulfides catalyzed by chloroperoxidaseBiochemistry, 1990
- Mechanism of S-oxidation reactions catalyzed by a soybean hydroperoxide-dependent oxygenaseBiochemistry, 1989
- Bromide-assisted hydrogen peroxide disproportionation catalyzed by vanadium bromoperoxidase: absence of direct catalase activity and implications for the catalytic mechanismInorganic Chemistry, 1989
- Isolation procedure and some properties of the bromoperoxidase from the seaweed Ascophyllum nodosumBiochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1985