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Issue 22, 2012
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Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters

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Abstract

A series of ortho-, meta-, and para- halogen-substituted methyl benzoate esters was subjected to enzymatic dihydroxylation via the whole-cell fermentation with E. coli JM109 (pDTG601A). Only ortho-substituted benzoates were metabolized. Methyl 2-fluorobenzoate yielded one diol regioselectively whereas methyl 2-chloro-, methyl 2-bromo- and methyl 2-iodobenzoates each yielded a mixture of regioisomers. Absolute stereochemistry was determined for all new metabolites. Computational analysis of these results and a possible rationale for the regioselectivity of the enzymatic dihydroxylation is advanced.

Graphical abstract: Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters

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Publication details

The article was received on 27 Jan 2012, accepted on 29 Mar 2012, published on 29 Mar 2012 and first published online on 29 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25202C
Citation: Org. Biomol. Chem., 2012,10, 4407-4416
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    Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters

    V. Semak, T. A. Metcalf, M. A. A. Endoma-Arias, P. Mach and T. Hudlicky, Org. Biomol. Chem., 2012, 10, 4407
    DOI: 10.1039/C2OB25202C

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