Probing the mycobacterial trehalome with bioorthogonal chemistry

Benjamin M. Swarts, Cynthia M. Holsclaw, John C Jewett, Marina Alber, Douglas M. Fox, M. Sloan Siegrist, Julie A. Leary, Rainer Kalscheuer, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

67 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)16123-16126
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number39
DOIs
StatePublished - Oct 3 2012

Fingerprint

Trehalose
Glycolipids
Mycobacterium
Alkynes
Azides
Disaccharides
Pathogens
Metabolites
Metabolic Networks and Pathways
Mycobacterium tuberculosis
Cell Wall
Labeling
Ligation
Labels
Visualization

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Swarts, B. M., Holsclaw, C. M., Jewett, J. C., Alber, M., Fox, D. M., Siegrist, M. S., ... Bertozzi, C. R. (2012). Probing the mycobacterial trehalome with bioorthogonal chemistry. Journal of the American Chemical Society, 134(39), 16123-16126. https://doi.org/10.1021/ja3062419

Probing the mycobacterial trehalome with bioorthogonal chemistry. / Swarts, Benjamin M.; Holsclaw, Cynthia M.; Jewett, John C; Alber, Marina; Fox, Douglas M.; Siegrist, M. Sloan; Leary, Julie A.; Kalscheuer, Rainer; Bertozzi, Carolyn R.

In: Journal of the American Chemical Society, Vol. 134, No. 39, 03.10.2012, p. 16123-16126.

Research output: Contribution to journalArticle

Swarts, BM, Holsclaw, CM, Jewett, JC, Alber, M, Fox, DM, Siegrist, MS, Leary, JA, Kalscheuer, R & Bertozzi, CR 2012, 'Probing the mycobacterial trehalome with bioorthogonal chemistry', Journal of the American Chemical Society, vol. 134, no. 39, pp. 16123-16126. https://doi.org/10.1021/ja3062419
Swarts, Benjamin M. ; Holsclaw, Cynthia M. ; Jewett, John C ; Alber, Marina ; Fox, Douglas M. ; Siegrist, M. Sloan ; Leary, Julie A. ; Kalscheuer, Rainer ; Bertozzi, Carolyn R. / Probing the mycobacterial trehalome with bioorthogonal chemistry. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 39. pp. 16123-16126.
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