Title

Investigation of New Mono-Halogenated Substrates of Benzoate Dioxygenase

Abstract

The transformation of arenes by microbial dioxygenases represents a powerful method for the production of chiral synthons in organic synthesis. We present an investigation of specific substrates of a benzoate dioxygenase from the bacterial strain Ralstonia eutropha B9. Several novel substrates were investigated with specific focus on mono-chloro and bromo substituted benzoates. After initial small volume transformation screening, those substrates that appeared viable were transformed on a larger scale in a bioreactor. We specifically present the conversion rates for the substrates 3-chlorobenzoic acid and 3-bromobenzoic acid, showing that these compounds are viable substrates for the highlighted benzoate dioxygenase. Also presented is a stereochemical proof of the absolute configurations of the presented biotransformation products. It is anticipated that these metabolites will open the door to new approaches to the natural product Epoxyquinol A, a heterodimeric epoxyquinoid that has been shown to inhibit angiogenesis.

Faculty Sponsor

Jon Collins

Tracks

poster

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Location

Cordiner Hall

Presentation Type

Poster

Research Funding Source or OCS Program

Sam Erickson: Perry Summer Research Award

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Apr 11th, 1:00 PM Apr 11th, 2:00 PM

Investigation of New Mono-Halogenated Substrates of Benzoate Dioxygenase

Cordiner Hall

The transformation of arenes by microbial dioxygenases represents a powerful method for the production of chiral synthons in organic synthesis. We present an investigation of specific substrates of a benzoate dioxygenase from the bacterial strain Ralstonia eutropha B9. Several novel substrates were investigated with specific focus on mono-chloro and bromo substituted benzoates. After initial small volume transformation screening, those substrates that appeared viable were transformed on a larger scale in a bioreactor. We specifically present the conversion rates for the substrates 3-chlorobenzoic acid and 3-bromobenzoic acid, showing that these compounds are viable substrates for the highlighted benzoate dioxygenase. Also presented is a stereochemical proof of the absolute configurations of the presented biotransformation products. It is anticipated that these metabolites will open the door to new approaches to the natural product Epoxyquinol A, a heterodimeric epoxyquinoid that has been shown to inhibit angiogenesis.

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