The transformation of arenes by microbial dioxygenases represents a powerful method for the production of chiral precursors in organic synthesis. The investigation of new substrates of a benzoate dioxygenase from the bacterial strain Ralstonia eutropha B9 will be presented. A focus of this work has been the screening of various mono-fluoro, chloro, bromo, iodo, hydroxy and methoxy substituted benzoates. Transformation of these substrates provided a variety of substituted ipso,ortho cis-dihydrodiol metabolites. The quantification of these reactions (e.g., activity and productivity) was performed using 1H-qNMR spectroscopic analysis of resting whole-cell cultures. The development of this method and its use to elucidate previously unknown trends in the substrate specificity of these dioxygenase systems will be presented. The ability of this method to facilitate analysis of unstable or transient metabolite will be highlighted.

Investigation of new benzoate-1,2-dioxygenase substrates using quantitative 1H-NMR spectroscopy

2019 Spring National Meeting

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