Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum
1999
Abstract It has been shown previously that the vanadium bromoperoxidase from Ascophyllum nodosum mediates the production of ( R )-methyl phenyl sulfoxide with 91% enantiomeric excess from the corresponding sulfide in the presence of hydrogen peroxide. Investigation of the sulfoxidation activity of this enzyme shows that activating substituents at the para -position of the aromatic ring of methyl phenyl sulfide positively influence the selectivity of the reaction, whereas strongly electron-withdrawing groups cancel the catalyzed sulfoxidation reaction. The first evidence is presented that the vanadium bromoperoxidase catalyzes the sulfoxidation of racemic non-aromatic cyclic thioethers with high kinetic resolution.
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