Probing the mycobacterial trehalome with bioorthogonal chemistry.

TitleProbing the mycobacterial trehalome with bioorthogonal chemistry.
Publication TypeJournal Article
Year of Publication2012
AuthorsSwarts BM, Holsclaw CM, Jewett JC, Alber M, Fox DM, M Siegrist S, Leary JA, Kalscheuer R, Bertozzi CR
JournalJ Am Chem Soc
Date Published2012 Oct 3
KeywordsAlkynes, Azides, Fluorescent Dyes, Glycolipids, Mycobacterium, Trehalose

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.

Alternate JournalJ. Am. Chem. Soc.
PubMed ID22978752
PubMed Central IDPMC3466019
Grant ListAI51622 / AI / NIAID NIH HHS / United States
R01 AI051622 / AI / NIAID NIH HHS / United States
/ / Howard Hughes Medical Institute / United States