SIDE-CHAIN OXIDATION OF AROMATIC-COMPOUNDS BY FUNGI .7. A RATIONALE FOR SULFOXIDATION, BENZYLIC HYDROXYLATION, AND OLEFIN OXIDATION BY MORTIERELLA-ISABELLINA

The fungus Mortierella isabellina ATCC 42613 catalyses the biotransfor mation of substituted-aryl methyl sulfides to give sulfoxides of predo minantly (R) configuration; of aryl-substituted alkenes to give chiral vicinal diols; and of various phenylalkanes and phenylcycloalkanes to give (R)-configuration benzylic alcohols. The nature of the products from all these processes may be accounted for by a single model based on restrictive space descriptors that can be used to rationalise these reactions, and which is proposed as a predictor of the outcome of the M. isabellina-catalyzed oxidations of similar substrates. (C) 1997 El sevier Science B.V.