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Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
- Swarts, Benjamin M;
- Holsclaw, Cynthia M;
- Jewett, John C;
- Alber, Marina;
- Fox, Douglas M;
- Siegrist, M Sloan;
- Leary, Julie A;
- Kalscheuer, Rainer;
- Bertozzi, Carolyn R
Published Web Location
https://doi.org/10.1021/ja3062419Abstract
Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Here we describe a strategy for exploiting trehalose metabolic pathways to label glycolipids in mycobacteria with azide-modified trehalose (TreAz) analogues. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome.
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