Jump to main content
Jump to site search

Issue 5, 2014
Previous Article Next Article

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

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Publication details

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
Citation: Chem. Sci., 2014,5, 1742-1744
  • Open access: Creative Commons BY license
  •   Request permissions

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

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

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements