Mycobacterium tuberculosis (Mtb) manifests itself in the form of human tuberculosis, which claims 1.3 million lives each year and is one of the top ten leading causes of deaths in the world. Although early detection can significantly reduce mortality rates for tuberculosis, currently available diagnostics have limitations with respect to specificity, sensitivity, and/or cost effectiveness. This research is aimed at the synthesis of new trehalose-based probes, which are designed to label mycobacteria via specific pathways 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 mycobacterial 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.

Synthesis of fluorogenic trehalose and trehalose monomycolate analogues for the detection of mycobacteria

2019 Fall National Meeting

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