Probing the Mycobacterial Trehalome with Bioorthogonal Chemistry
Open accessAbstract
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.
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Bioorthogonal metabolic labeling allows the biosynthesis of trehalose-containing molecules, peptidoglycans, and arabinan to be visualized in situ in both M. smegmatis and M. tuberculosis.
“Nevertheless, there are emerging efforts to apply modern (click chemistry) approaches of bioorthogonal metabolic labeling in both M. smegmatis and M. tuberculosis, allowing the biosynthesis of trehalose-containing molecules, peptidoglycans, and arabinan to be visualized in situ (116, 163–165).”
From Mycobacterium smegmatis: The Vanguard of Mycobacterial Research (2023) · cites this paper as [163]
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- Authors
- Swarts, B. M., Holsclaw, C. M., Jewett, J. C., Alber, M., Fox, D. M., Siegrist, M. S., Leary, J. A., Kalscheuer, R., & Bertozzi, C. R.
- Affiliations
- University of California, Berkeley (US)
- Howard Hughes Medical Institute (US)
- Heinrich Heine University Düsseldorf (DE)
- Corresponding author
- Bertozzi, Carolyn R.
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-09-24
- Volume
- 134
- Issue
- 39
- Pages
- 16123-16126
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- PMC
- PMC3466019
- OpenAlex
- W2417424384
- Cited by
- 184
- References
- 25
- Citations by year
- 2026: 8 · 2025: 13 · 2024: 19 · 2023: 18 · 2022: 17 · 2021: 16 · 2020: 14 · 2019: 11 · 2018: 18 · 2017: 10 · 2016: 8 · 2015: 10 · 2014: 12 · 2013: 10
- FWCI
- 4.70
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of the American Chemical Society (publishedVersion, other-oa)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- eScholarship (California Digital Library) (submittedVersion)
- Funders
- American Chemical Society
- National Institutes of Health
- Office of the Vice Chancellor for Research University of Illinois at Urbana-Champaign
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Health Sciences › Medicine › Infectious Diseases › Tuberculosis Research and Epidemiology
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › Biotin and Related Studies
- Keywords
- trehalose, Mycobacterium tuberculosis, mycobacteria, bioorthogonal labeling, bioorthogonal ligation, trehalose metabolism
- MeSH terms
- Alkynes, Azides, Fluorescent Dyes, Glycolipids, Mycobacterium, Trehalose
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