Synthesis and evaluation of flouro and thia lipids as bioanalytical tools

 

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dc.contributor.advisor Jardine, Anwar en_ZA
dc.contributor.advisor Chibale, Kelly en_ZA
dc.contributor.author Manuel, Gaynor en_ZA
dc.date.accessioned 2015-07-03T08:35:36Z
dc.date.available 2015-07-03T08:35:36Z
dc.date.issued 2014 en_ZA
dc.identifier.citation Manuel, G. 2014. Synthesis and evaluation of flouro and thia lipids as bioanalytical tools. University of Cape Town. en_ZA
dc.identifier.uri http://hdl.handle.net/11427/13361
dc.description Includes bibliographical references. en_ZA
dc.description.abstract Lipid catabolism plays a significant role in the survival of M.tb inside the host. The development of analytical techniques such as gas chromatography mass spectroscopy (GCMS) and liquid chromatography mass spectroscopy (LC-MS) has become popular as metabolomics tools in the study of such catabolic pathways. The development of biomarkers and internal standards to perform quantitative and qualitative analysis of metabolites in the catabolic pathway would be an attractive tool. Thus, cholesterol derivatives were synthesized as thia-, fluoro- and deuterium labeled analogs. Sulfur was incorporated into cholesterol at positions, C3 as well as C23. The 3â-mercaptocholest-5-ene was synthesized to block the initial stage of cholesterol catabolism and evaluate whether side chain degradation can still occur. Fluorine was integrated into the cholesterol backbone at C3 to evaluate the side-chain degradation in the absence of cholesterol oxidase activity. Steroids with fluorine at C6 are known to have good biological activity and were for this reason also synthesized. Deuterium labeled compounds were synthesized and used as internal standards for GC-MS analysis. As an alternative to cholesterol catabolism, fatty acids like stearic acid are important in producing building blocks for long chain mycolic acids which provides protection to the mycobacterium. For this reason thiastearic acid derivatives were synthesized and evaluated as biomarkers. en_ZA
dc.language.iso eng en_ZA
dc.subject.other Chemistry en_ZA
dc.title Synthesis and evaluation of flouro and thia lipids as bioanalytical tools en_ZA
dc.type Thesis / Dissertation en_ZA
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Masters en_ZA
dc.type.qualificationname MSc en_ZA
uct.type.filetype Text
uct.type.filetype Image


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