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Issue 5, 2014
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Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition

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The discovery and exploration of bioorthogonal chemical reactions and the biosynthetic incorporation of their components into biomolecules for specific labelling is an important challenge. Here we describe the reaction of a phenyl sydnone 1,3-dipole with a bicyclononyne dipolarophile. This strain-promoted reaction proceeds without transition metal catalysis in aqueous buffer, at physiological temperature, and pressure with a rate comparable to that of other bioorthogonal reactions. We demonstrate the quantitative and specific labelling of a genetically encoded bicyclononyne with a sydnone fluorophore conjugate, demonstrating the utility of this approach for bioorthogonal protein labelling.

Graphical abstract: Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition

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The article was received on 05 Dec 2013, accepted on 22 Jan 2014 and first published on 05 Feb 2014

Article type: Edge Article
DOI: 10.1039/C3SC53332H
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Citation: Chem. Sci., 2014,5, 1742-1744
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    Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition

    S. Wallace and J. W. Chin, Chem. Sci., 2014, 5, 1742
    DOI: 10.1039/C3SC53332H

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