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Probing the mycobacterial trehalome with bioorthogonal chemistry.

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.

SUBMITTER: Swarts BM

PROVIDER: S-EPMC3466019 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Probing the mycobacterial trehalome with bioorthogonal chemistry.

Swarts Benjamin M BM Holsclaw Cynthia M CM Jewett John C JC Alber Marina M Fox Douglas M DM Siegrist M Sloan MS Leary Julie A JA Kalscheuer Rainer R Bertozzi Carolyn R CR

Journal of the American Chemical Society 20120924 39

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 m ...[more]

PMID: 22978752

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