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

Probing the mycobacterial trehalome with bioorthogonal chemistry.

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1
Department of Chemistry, University of California, Berkeley, California 94720, USA.

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.

PMID:
22978752
PMCID:
PMC3466019
DOI:
10.1021/ja3062419
[Indexed for MEDLINE]
Free PMC Article
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