Jump to main content
Jump to site search

Issue 2, 2016
Previous Article Next Article

Discovery of new mutually orthogonal bioorthogonal cycloaddition pairs through computational screening

Author affiliations

Abstract

Density functional theory (DFT) calculations and experiments in tandem led to discoveries of new reactivities and selectivities involving bioorthogonal sydnone cycloadditions. Dibenzocyclooctyne derivatives (DIBAC and BARAC) were identified to be especially reactive dipolarophiles, which undergo the (3 + 2) cycloadditions with N-phenyl sydnone with the rate constant of up to 1.46 M−1 s−1. Most significantly, the sydnone-dibenzocyclooctyne and norbornene-tetrazine cycloadditions were predicted to be mutually orthogonal. This was validated experimentally and used for highly selective fluorescence labeling of two proteins simultaneously.

Graphical abstract: Discovery of new mutually orthogonal bioorthogonal cycloaddition pairs through computational screening

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Aug 2015, accepted on 11 Nov 2015 and first published on 11 Nov 2015


Article type: Edge Article
DOI: 10.1039/C5SC03259H
Author version
available:
Download author version (PDF)
Chem. Sci., 2016,7, 1257-1261
  • Open access: Creative Commons BY license
  •   Request permissions

    Discovery of new mutually orthogonal bioorthogonal cycloaddition pairs through computational screening

    M. K. Narayanam, Y. Liang, K. N. Houk and J. M. Murphy, Chem. Sci., 2016, 7, 1257
    DOI: 10.1039/C5SC03259H

    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