Issue 36, 2011
From the journal:

Chemical Communications

Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells†

Craig S. McKay,ab   Jessie A. Blake,ab   Jenny Cheng,a   Dana C. Danielsonac  and  John Paul Pezacki*abc  

* Corresponding authors

a Steacie Institute for Molecular Sciences, National Research Council Canada, Ottawa, Canada
E-mail: John.Pezacki@nrc-cnrc.gc.ca
Fax: +1 613-952-0068
Tel: +1 613-993-7253

b Department of Chemistry, University of Ottawa, Ottawa, Canada

c Department of Biochemistry, Microbiology and Immunology, University of Ottawa, Ottawa, Canada

Abstract

Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes proceed with rate constants up to 3.38 ± 0.31 M−1 s−1 in CD3CN, or 59 times faster than the analogous reaction of azides. This highly specific modular labeling strategy can be applied for direct labeling of proteins and for live cell imaging of cancer cells.

Graphical abstract: Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells

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Article information

DOI
https://doi.org/10.1039/C1CC13808A
Article type
Communication
Submitted
26 Jun 2011
Accepted
21 Jul 2011
First published
10 Aug 2011

Chem. Commun., 2011,47, 10040-10042

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Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells

C. S. McKay, J. A. Blake, J. Cheng, D. C. Danielson and J. P. Pezacki, Chem. Commun., 2011, 47, 10040 DOI: 10.1039/C1CC13808A

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