Journal
CHEMICAL SCIENCE
Volume 5, Issue 5, Pages 1742-1744Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc53332h
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Funding
- Medical Research Council, UK [U105181009, UD99999908]
- Medical Research Council
- MRC [MC_UP_A024_1008] Funding Source: UKRI
- Medical Research Council [MC_UP_A024_1008] Funding Source: researchfish
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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.
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