Tuberculosis has re-emerged as one of the world’s greatest pathological threats. However, many of the chemical processes governing the mycobacteria causing tuberculosis remain unexplored. An example is the mycobacterial cell wall, which contains an important carbohydrate substructure known as arabinogalactan. Arabinogalactan consists of arabinofuranose side-chains linked to a galactofuranose backbone. Arabinogalactan-degrading endo-galactofuranosidase activity has been discovered, however, endo-galactofuranosidase enzymes capable of degrading arabinogalactan remain unidentified. In this thesis, synthetic routes towards activity based probes capable of identifying these enzymes were further developed. These probes consisted of galactofuranose disaccharides equipped with epoxide warheads and biotin or BODIPY tags. Various synthetic routes for the acceptor moieties of the probes were developed, until a sufficient one was discovered. A glycosylation procedure for the synthesis of one of the probes was also developed.
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