Probing the Mycobacterial
Trehalome with Bioorthogonal
Chemistry
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Abstract
Mycobacteria, including the pathogen <i>Mycobacterium
tuberculosis</i>, 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