Ashton Drake / Chemistry & Biochemistry / Faculty Mentor: Joseph Buonomo
Mycobacterium tuberculosis is the causative agent of the transmissible disease tuberculosis. The complex structure of the mycobacterial cell wall contributes to its successful virulence. Of particular interest is the Mycobacterial membrane protein Large 3 (MmpL3), a mycolic acid and lipid transporter that has been widely viewed as a potential drug target. MmpL3 is required for the transport of trehalose monomycolates (TMMs) across the cell membrane for cell wall synthesis. A set of TMM analogs was prepared via the addition of N-methylhydroxylamine, N-hydroxylamine, and N3 at the 6-position. Various synthetic routes were explored and subsequently analyzed based on selectivity, scalability, and yield. Each was effective in preparing all analogs and has exhibited effectiveness in M. smegmatis which has permitted the imaging and mapping of the TMM population.
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