Synthesis and evaluation of flouro and thia lipids as bioanalytical tools

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dc.contributor.advisorJardine, Anwaren_ZA
dc.contributor.advisorChibale, Kellyen_ZA
dc.contributor.authorManuel, Gaynoren_ZA
dc.date.accessioned2015-07-03T08:35:36Z
dc.date.available2015-07-03T08:35:36Z
dc.date.issued2014en_ZA
dc.descriptionIncludes bibliographical references.en_ZA
dc.description.abstractLipid 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.identifier.apacitationManuel, G. (2014). <i>Synthesis and evaluation of flouro and thia lipids as bioanalytical tools</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/13361en_ZA
dc.identifier.chicagocitationManuel, Gaynor. <i>"Synthesis and evaluation of flouro and thia lipids as bioanalytical tools."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2014. http://hdl.handle.net/11427/13361en_ZA
dc.identifier.citationManuel, G. 2014. Synthesis and evaluation of flouro and thia lipids as bioanalytical tools. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Manuel, Gaynor AB - 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. DA - 2014 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2014 T1 - Synthesis and evaluation of flouro and thia lipids as bioanalytical tools TI - Synthesis and evaluation of flouro and thia lipids as bioanalytical tools UR - http://hdl.handle.net/11427/13361 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/13361
dc.identifier.vancouvercitationManuel G. Synthesis and evaluation of flouro and thia lipids as bioanalytical tools. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2014 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/13361en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleSynthesis and evaluation of flouro and thia lipids as bioanalytical toolsen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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