Bioconversion of substituted naphthalenes to the corresponding 1,2-dihydro-1,2-dihydroxy derivatives. Determination of the regio- and stereochemistry of the oxidation reactions

• DOI: 10.1007/bf00169921
• Publication Date: 2004-08-14T19:57:29Z
• Authors: G. Bestetti; D. Bianchi; A. Bosetti; P. Di Gennaro; E. Galli; B. Leoni; F. Pelizzoni; G. Sello
• Keywords: Bioconversion; Absolute Configuration; Enantiomeric excess; Biotransformation; Pseudomonas fluorescens

A mutant (TTC1) derived from Pseudomonas fluorescens N3 has been obtained for use in the bioconversion of several naphthalene derivatives to the corresponding optically active cis-dihydrodiols on a milligrams-to-grams scale. All main compounds have been characterized, their relative and absolute configuration assigned, and their enantiomeric purity determined. The regio- and stereoselectivity of the transformation has been established. The procedure therefore represents a valid method for the convenient preparation of a pool of valuable chiral syntons and auxiliaries.