| Summary: | This thesis describes the application of a number of whole cell systems to the hydroxylation of organic compounds and thus the production of high value synthetic intermediates. Such transformations are currently very difficult, or impossible to achieve using purely synthetic techniques. Biocatalysis on the other hand, offers the potential to achieve this process in a mild, regio- and stereoselective manner. A range of compounds comprised of a carbo- or heterocycle attached <i>via</i> a linker to an aromatic group have been prepared. These compounds were screened as potential substrates with a number of whole cell systems thought to contain cytochromes P-450. Subsequent biotransformation, product isolation and characterisation are described. Investigation of the biohydroxylation of a series of <i>N</i>-carboxybenzylalkylpiperidines by <i>Beauveria bassiana</i> ATCC 7159 and study of the factors important to the selectivity of hydroxylation by the organism is illustrated. Research into the biohydroxylation capabilities of two members of the <i>Rhodococcus </i>genus has also been carried out. <i>Rhodococcus</i> sp. NCIMB 9784 and <i>Rhodococcus rhodochrous </i>NCIMB 9703 were found to be suitable biocatalysts for the hydroxylation of non-natural substrates. Subsequent exploration of the regio- and enantioselectivity of this hydroxylation process is discussed.
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