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Title: Synthesis of myobacterial wax esters and related compounds
Author: Taher, Salam Ghafour
ISNI:       0000 0004 5364 5291
Awarding Body: Bangor University
Current Institution: Bangor University
Date of Award: 2014
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Mycobacteria are present in a wide range of environments. They contain characteristic complex mixtures of mycolic acids in the cell wall together with other lipids. The high resistance of mycobacteria to the majority of antibiotics, therapeutic agents and disinfectants is thought to be related to the unique structure of the mycobacterial cell wall. Mycolic acids are high molecular weight a-alkyl-branched B-hydroxy long chain fatty acids (60-90 carbon atoms). Different species of Mycobacteria may produce different classes of mycolic acids including a-, methoxy, keto, and wax ester mycolic acids, each present as mixtures of homologues. These may contain different functional groups such as ester, keto, methoxy, hydroxyl, and alkene. The most reported lipids present in the cell wall are sugar esters, e.g mycolyl trehalose esters. These mycolic acids and mycolyl trehalose esters show very interesting toxic and immunological properties; these offer considerable potential for application in the detection, control, and treatment of mycobacterial infection, and also in developing sensors for detection of disease. This study will seek to explore these potentials. This project involved the synthesis of several mycolic acids, wax esters and trehalose esters. The biological activities of these synthetic compounds would be studied, particularly their suitability as specific antigens to detect mycobacterial infections in serodiagnostic assays. The objectives of the project are discussed in four parts. The first part of this project involved the first synthesis of wax ester (A) and its corresponding ω-carboxymycolic acid (B), one component of the complex mixture isolated from Mycobacterium avium. Once the synthesis had been optimised, synthesis of the wax ester (C) and its corresponding ω-carboxymycolic acid (D) were also achieved, the latter compounds being isolated from Mycobacterium gordonae. In addition the wax ester (E) was also prepared introducing longer chain lengths than the natural wax ester. This was to study whether or not the chain length has any effect on the biological activities.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available