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Oxidation-Controlled, Strain-Promoted Tellurophene-Alkyne Cycloaddition (OSTAC): A Bioorthogonal
Yong Jia Bu1, Santiago Tijaro-Bulla1, Haissi Cui1
1Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada.
Journal of the American Chemical Society
|September 11, 2024
Summary
Researchers developed a new bioorthogonal reaction for tagging tellurophene-containing molecules. This oxidation-controlled, strain-promoted tellurophene-alkyne cycloaddition (OSTAC) reaction enables selective protein labeling in complex biological samples.
Area of Science:
- Chemical Biology
- Organic Chemistry
- Bioconjugation
Background:
- Tellurophene-bearing molecules are used for in vivo cellular activity localization via mass cytometry.
- Expanding the utility of tellurophenes in chemical biology requires new bioorthogonal tagging methods.
Purpose of the Study:
- To develop a novel bioorthogonal reaction for tagging tellurophene-containing conjugates.
- To enable downstream applications of tellurophene-based probes in chemical biology.
Main Methods:
- Utilized a tellurophene-based phenylalanine analogue (TePhe) to generate labeled recombinant proteins.
- Demonstrated an oxidation-controlled, strain-promoted tellurophene-alkyne cycloaddition (OSTAC) reaction.
- Employed mild oxidation of tellurophene with N-chlorosuccinimide followed by cycloaddition with bicyclo[6.1.0]nonyne (BCN).
Main Results:
- Achieved selective labeling of TePhe-containing proteins in complex mixtures and fixed cells.
- The OSTAC reaction proceeds rapidly (k > 100 M-1 s-1) to form a benzo-fused cyclooctane.
- Demonstrated compatibility of OSTAC with strain-promoted azide alkyne cycloaddition (SPAAC) and copper-catalyzed azide alkyne click (CuAAC) reactions.
Conclusions:
- The OSTAC reaction offers a versatile and efficient method for bioorthogonal labeling.
- This approach allows for simultaneous detection of different biomolecules, such as DNA and proteins, in fixed cells.
- The favorable properties of OSTAC suggest broad applicability in chemical biology research.
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