Synthesis of mycolic acids and related sugar ester

Abstract

This study involved the preparation of mycolic acid (II) containing a double bond in a cis configuration. This was attempted by hydrogenation of an alkyne, which was successful in model reactions, but gave no evidence of success when applied to the mycolic acid. The other strategy was the use of a Wittig reaction. In order to optimise the conditions for double bond synthesis, a small mycolic acid (I) was first synthesised since it is reported in corynobacteria diphtheriae.
Once the reaction conditions had been optimised, the same conditions were applied for the synthesis of mycolic acid (II) and mycolic acid (III).
This was followed by unsuccessful attempt to synthesise saturated mycolic acid (IV).
Three other mycolic acids were made; a hydroxy mycolic acid (V), which contains a hydroxy group in the meromycolate moiety, a keto mycolic acid (VI) containing a keto group in the meromycolate moiety and a-mycolic acid (VII), with two
cyclopropane rings in the meromycolate moiety.
In the last stages of this study, the synthesis of cord factors of mycolic acids became the focus. Two separate trehalose dimycolates (TDMs) of a-mycolic acids (II and VII) were synthesised, followed by the synthesis of the free trehalose monomycolate (TMM) of a -mycolic acid (VII), and the protected TMM of mycolic acid (II).

Date of Award	2012
Original language	English
Awarding Institution	Bangor University
Sponsors	Ministry of Higher Education and Cultural Attache
Supervisor	Mark Baird (Supervisor)