Dan Gepford

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Dan Gepford
Mentor:  Dr. Ben Swarts

Synthesis of Fluorogenic Trehalose and Trehalose Monomycolate Analogues for the Detection of Mycobacteria
Mycobacterium tuberculosis (Mtb) manifests itself in the form of human tuberculosis, which claims 1.3 million lives each year. Although early detection can significantly reduce mortality rates for tuberculosis, currently available diagnostics have limitations. This research is aimed at the synthesis of new trehalose-based probes, which are designed to label mycobacteria and thus may enable rapid and accurate detection of Mtb infections. Here, the syntheses of trehalose and trehalose monomycolate (TMM) analogues bearing molecular rotor-based fluorogenic moieties that operate through a twisted intramolecular charge transfer (TICT) mechanism are reported. It is hypothesized that upon incorporation into the densely packed outer membrane, probe rotation will be restricted, generating fluorescence. For comparison, a previously reported solvatochromism-based fluorogenic trehalose analogue and its TMM version were also synthesized.