Probing the mycobacterial trehalome with bioorthogonal chemistry

J Am Chem Soc. 2012 Oct 3;134(39):16123-6. doi: 10.1021/ja3062419. Epub 2012 Sep 24.


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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Fluorescent Dyes / chemistry
  • Glycolipids / metabolism
  • Mycobacterium / metabolism*
  • Trehalose / chemistry*
  • Trehalose / metabolism*


  • Alkynes
  • Azides
  • Fluorescent Dyes
  • Glycolipids
  • Trehalose