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Title: Small molecule approaches to enzyme mechanisms
Author: Dean, K. E. S.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2000
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This dissertation discusses several different approaches towards a better understanding of enzyme mechanisms. After a brief introduction to enzyme catalysis there is a general review of acetal hydrolysis and previous investigations into the mechanism of glycoside hydrolysis catalysed by lysozyme. The third chapter describes studies towards the synthesis of a serine protease model. The remaining three chapters discuss investigations into the mechanism of lysozyme, through the use of substrate models, proton transfer models and a bifunctional catalysis model. After an introduction to the catalysis of peptide hydrolysis by the serine proteases, the design and studies towards the synthesis of an oxyanion hole model are described in Chapter 3. A collaborative project investigating different steric and electronic effects on acetal hydrolysis in lysozyme substrate models is presented in Chapter 4. After a brief overview of the conception and aims of the project, details of the synthesis of some of the models are given, and the results of kinetic analyses of all the model compounds are discussed. The study of ethers of salicyclic acids is described in Chapter 5. Although the aromatic system is not a good enzyme model these compounds were designed in order to investigate the efficiency of the intramolecular proton transfer catalysis and to determine whether the hydrolysis of relatively unreactive substrates could be catalysed. Two catalytic groups are involved in the mechanism of lysozyme. The final chapter details the design and synthesis of a model containing two functional groups positioned to attack an acetal carbon. Kinetic studies of the hydrolysis of the model and a discussion of the results obtained are presented.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available