Isolation and structure determination of the metabolites from Pseudomonas putida 39D: oxidation of di-substituted aromatics

Abstract

m-Bromotrifluorotoluene, 1, was subjected to microbial oxidation by Pp 39/D. The products from the reaction were isolated and identified by various spectral techniques. The absolute stereochemistry of the major metabolite has been determined as cis-ααα-trifluoromethyl 2R, 3S-dihydroxy-5-bromo-4,6-cyclohexadiene 2.

The absolute stereochemistry was discovered by comparison of the products from the convergent synthetic pathway of 2 and the known diol metabolite from α,α,α-trifluorotoluene, 4.