Trehalose is an essential metabolite in <i>Mycobacterium tuberculosis </i>but it is absent from humans, making it an attractive target for tuberculosis drug and diagnostic development. Modified versions of trehalose, called trehalose analogues, have potential as probes and inhibitors of trehalose metabolic pathways in mycobacteria, as underscored by the recent development of trehalose-based, mycobacteria-specific imaging probes. Unfortunately, the chemical synthesis of trehalose analogues remains challenging due to the difficulties associated with its unique 1,1-α,α-glycosidic bond. In a project led by undergraduate researchers, our labs have developed a one-step chemoenzymatic method for synthesizing trehalose analogues that bypasses these challenges and allows rapid access to a variety of these structures. The development and use of this method to synthesize trehalose analogues, as well as the evaluation of these compounds as probes and inhibitors of mycobacterial trehalose metabolism, are discussed here.

Trehalose analogues: New synthetic methods and applications in mycobacteria research

251st National Meeting (2016)

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