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dc.contributor.authorFroese, Jordan
dc.date.accessioned2016-09-13T17:50:48Z
dc.date.available2016-09-13T17:50:48Z
dc.identifier.urihttp://hdl.handle.net/10464/10408
dc.description.abstractThe substrate scope and selectivity of toluene dioxygenase overexpressed in E.coli JM109 (pDTG601A) was investigated with series of ortho-halobenzoates and para-substituted arenes. Palladium-catalyzed carbonylation methodology was developed to convert halogenated cis-dihydrodiol metabolites to the corresponding carboxylates and a comparison of the overall efficiency between the enzymatic and chemical methods of access was made. Some of the metabolites produced by toluene dioxygenase were employed in a synthetic approach toward tetrodotoxin. Enzymatic dihydroxylation of benzoic acid with R. eutropha B9 provided the corresponding ipso-diol that was used in the first total synthesis of pleiogenone A, a bioactive natural product. Experimental and spectral data are provided for all new compounds.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectbiocatalysis, toluene dioxygenase, total synthesisen_US
dc.titleThe production and synthetic utility of the dioxygenase-derived metabolites of substituted aromaticsen_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.namePh.D. Biotechnologyen_US
dc.degree.levelDoctoralen_US
dc.contributor.departmentCentre for Biotechnologyen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
refterms.dateFOA2021-08-02T02:01:16Z


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