Collect. Czech. Chem. Commun. 2005, 70, 1709-1726

Toluene Dioxygenase-Mediated Oxidation of Bromo(methylsulfanyl)benzenes. Absolute Configuration of Metabolites and Evaluation of Chemo- and Regioselectivity Trends

Kevin J. Finn, Oksana Pavlyuk and Tomáš Hudlický*

Department of Chemistry, Brock University, St. Catharines, Ontario, Canada L2S 3A1


A series of 2-, 3-, and 4-bromo-1-(methylsulfanyl)benzenes was subjected to whole-cell fermentation with Escherichia coli JM 109 (pDTG601), a recombinant strain that expresses toluene dioxygenase. New metabolites were isolated and their structure and absolute configuration determined by chemical and spectral methods. Experimental details are provided for all new compounds and directing trends in the enzymatic oxidation of substituted aromatics are discussed along with projected applications of these metabolites in asymmetric synthesis.

Keywords: Biotransformations; Toluene dioxygenase; Enzymatic sulfur oxidations; Whole-cell fermentations; Dienediols; Dioxygenations; Chiral building blocks; Diols; Asymmetric synthesis.

References: 35 live references.