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Towards the Industrial Application of the Baeyer-Villiger Monooxygenase MO14 from Rhodococcus jostii

Summers, Benjamin (2014) Towards the Industrial Application of the Baeyer-Villiger Monooxygenase MO14 from Rhodococcus jostii. PhD thesis, University of York.

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Abstract

The Baeyer-Villiger reaction is a key reaction in organic synthesis, due to the utility of the addition of an oxygen atom adjacent to a carbonyl group. This reaction is also useful in an industrial setting and Baeyer-Villiger monooxygenases are often capable of performing this reaction in an exceptionally regio- and enantio-selective manner. This remarkable selectivity means that they are excellent biocatalyst targets for a number of industrially relevant syntheses, including the stereoselective synthesis of lactones and sulfoxides and also the resolution of racemic species, including �-hydroxyketones. This PhD project focussed on the enzyme MO14, encoded by the gene ro03437 from the bacterium Rhodococcus jostii sp. RHA1. MO14 has previously demonstrated particularly high regioand enantioselectivity in the conversion of the model BVMO substrate, bicyclo[3.2.0]hept-2-en-6- one. This enzyme, along with several others from the same organism, was selected for study of the activity and MO14 in particular has been singled out due to its remarkable breadth of substrate scope and S-selective character. All of the selected enzymes were tested against a selection of industrially relevant targets, then focus concentrated on MO14, as it demonstrated the most interesting biocatalytic activities. A variety of purification strategies were examined for the purification of MO14, with several potential lines of enquiry identified for the full purification of this enzyme. A study of the transformation of bicyclo[3.2.0]hept-2-en-6-one was conducted, with several variables of the reaction assessed, followed by investigation of the ability of this enzyme to transform a range of prochiral sulfides. As a precursor to industrial applications, a series of scale-up reactions were conducted using MO14 to examine the potential for use on a scale much larger than standard laboratory investigation. Finally, a series of mutants were generated to examine the origin of the exceptional selectivity exhibited by this enzyme.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Identification Number/EthosID: uk.bl.ethos.638995
Depositing User: Mr Benjamin Summers
Date Deposited: 03 Mar 2015 11:15
Last Modified: 08 Sep 2016 13:32
URI: http://etheses.whiterose.ac.uk/id/eprint/8097

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