Strain-promoted sydnone bicyclo-6.1.0-nonyne cycloaddition†Electronic supplementary information (ESI) available: Full experimental details, 1H/13C NMR spectral data, protein synthesis and purification. See DOI: 10.1039/c3sc53332h

• Published in: Chemical science (Cambridge) Vol. 5; no. 5; p. 1742
• Main Authors: Wallace, Stephen, Chin, Jason W
• Format: Journal Article
• Language: English
• Published: 01.04.2014
• ISSN: 2041-6520
• DOI: 10.1039/c3sc53332h

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.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.