The production and synthetic utility of the dioxygenase-derived metabolites of substituted aromatics
dc.contributor.author | Froese, Jordan | |
dc.date.accessioned | 2016-09-13T17:50:48Z | |
dc.date.available | 2016-09-13T17:50:48Z | |
dc.identifier.uri | http://hdl.handle.net/10464/10408 | |
dc.description.abstract | The 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.iso | eng | en_US |
dc.publisher | Brock University | en_US |
dc.subject | biocatalysis, toluene dioxygenase, total synthesis | en_US |
dc.title | The production and synthetic utility of the dioxygenase-derived metabolites of substituted aromatics | en_US |
dc.type | Electronic Thesis or Dissertation | en |
dc.degree.name | Ph.D. Biotechnology | en_US |
dc.degree.level | Doctoral | en_US |
dc.contributor.department | Centre for Biotechnology | en_US |
dc.degree.discipline | Faculty of Mathematics and Science | en_US |
refterms.dateFOA | 2021-08-02T02:01:16Z |