Issue 5, 2014

Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition


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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Article information

Article type
Edge Article
05 Dec 2013
22 Jan 2014
First published
05 Feb 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 1742-1744

Author version available

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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