Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
| Autor: | Rainer Kalscheuer, Carolyn R. Bertozzi, John C. Jewett, Marina Alber, Cynthia M. Holsclaw, Julie A. Leary, Benjamin M. Swarts, Douglas M. Fox, M. Sloan Siegrist |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Azides
Disaccharide 01 natural sciences Biochemistry Catalysis Mycobacterium Mycobacterium tuberculosis 03 medical and health sciences chemistry.chemical_compound Colloid and Surface Chemistry Glycolipid Pathogen Fluorescent Dyes 030304 developmental biology 0303 health sciences biology 010405 organic chemistry Communication Trehalose General Chemistry biology.organism_classification 3. Good health 0104 chemical sciences Metabolic pathway chemistry Alkynes Glycolipids Bioorthogonal chemistry |
| Zdroj: | Journal of the American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja3062419 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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