Abstract
Studies on the sulfoxidation of aryl alkyl sulfides by purified toluene dioxygenase and naphthalene dioxygenase showed that naphthalene dioxygenase produces sulfoxides of ( S) absolute configuration in high enantiomeric purity while those formed by toluene dioxygenase are of variable enantiomeric purity depending on the p-substituents on the benzene ring. Oxygen uptake experiments with naphthalene dioxygenase showed that the reaction rate and degree of oxygen incorporation are affected by both aryl and alkyl substituents. 18O 2-Incorporation experiments showed that the oxygen atom of methyl phenyl sulfoxide formed by toluene dioxygenase and naphthalene dioxygenase is derived exclusively from O 2. Accompanying studies showed that chloroperoxidase produces single ( R)-sulfoxides (>98% enantiomeric excess) from the aryl alkyl sulfides examined in the present study.
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