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Probing the mycobacterial trehalome with bioorthogonal chemistry.

  • Author(s): Swarts, Benjamin
  • Holsclaw, Cynthia
  • Jewett, John
  • Alber, Marina
  • Fox, Douglas
  • Siegrist, M
  • Leary, Julie
  • Kalscheuer, Rainer
  • Bertozzi, Carolyn
  • et al.

Published Web Location

https://doi.org/10.1021/ja3062419
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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