Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
Journal of the American Chemical Society2012Vol. 134(39), pp. 16123–16126
Citations Over TimeTop 10% of 2012 papers
Benjamin M. Swarts, Cynthia M. Holsclaw, John C. Jewett, Marina Alber, Douglas Fox, M. Sloan Siegrist, Julie A. Leary, Rainer Kalscheuer, Carolyn R. Bertozzi
Abstract
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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