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Published on: August 19, 2012
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The Bioorthogonal Isonitrile-Chlorooxime Ligation
Rebecca J B Schäfer1, Mattia R Monaco1, Mao Li1
1Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
Journal of the American Chemical Society
|November 12, 2019
Summary
A new bioorthogonal reaction between isonitriles and chlorooximes offers rapid, selective labeling in aqueous environments. This method is compatible with cellular systems and orthogonal to other bioconjugation techniques.
Area of Science:
- Chemical Biology
- Organic Chemistry
- Bioconjugation Chemistry
Background:
- Bioorthogonal reactions are crucial for selectively labeling and imaging biomolecules in complex biological systems.
- Existing methods often face limitations in speed, selectivity, or compatibility with aqueous environments.
Purpose of the Study:
- To introduce and characterize a novel ligation reaction between isonitriles and chlorooximes for bioorthogonal applications.
- To demonstrate the utility of this ligation in cellular imaging and its orthogonality to established bioorthogonal reactions.
Main Methods:
- Investigated the kinetics and chemoselectivity of the isonitrile-chlorooxime ligation in aqueous solution.
- Applied the ligation to image metabolically labeled cell surface glycans.
- Performed live-cell dual-labeling experiments to assess orthogonality with strain-promoted azide-alkyne cycloaddition (SPAAC).
Main Results:
- The isonitrile-chlorooxime ligation proceeds rapidly (k ≈ 1 M⁻¹ s⁻¹) with high chemoselectivity in water.
- The reaction demonstrated tolerance to various functional groups present in cellular environments.
- Dual-labeling experiments confirmed the orthogonality of this ligation to SPAAC in live cells.
Conclusions:
- The isonitrile-chlorooxime ligation is a robust and efficient new tool for bioorthogonal chemistry.
- Its speed, selectivity, and orthogonality make it suitable for advanced cellular imaging and labeling applications.
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