Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671

Article abstract of DOI:10.1016/S0957-4166(97)00006-2

The fungus Helminthosporium species NRRL 4671 converts a wide range of prochiral sulfides to the corresponding chiral sulfoxides, the majority of which have (S) configuration at sulfur. The formation of a series of chiral cyclopentyl alkyl, cyclohexyl alkyl, benzyl alkyl, and methyl alkyl sulfoxides by biotransformation of the corresponding sulfides using Helminthosporium species is described. The analysis of over 90 such biotransformations has resulted in the development of a model based on restrictive-space descriptors that has been used to rationalize these reactions, and that is proposed as a predictor of the outcome of Helminthosporium-catalyzed sulfoxidations.