New Diol Metabolites Derived by Biooxidation of Chlorostyrenes with Pseudomonas putida: Determination of Absolute Stereochemistry and Enantiomeric Excess by Convergent Syntheses

Article abstract of DOI:10.1016/S0957-4166(00)80247-5

The three isomers of chlorostyrenes were subjected to whole cell biooxidation by means of a mutant strain of Pseudomonas putida 39D.The metabolites were isolated and their absolute stereochemistry determined by conversion to known standards derived from 1-ethenyl-2,3-dihydroxycyclohexa-4,6-diene whose absolute configuration has been previously established.The extent of ring vs side chain oxidation of the chlorostyrene isomers was evaluated and the enantiomeric excess determined for all compounds.