Issue 21, 2013
From the journal:

Organic & Biomolecular Chemistry

Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry†

Mariya Chigrinova,ab   Craig S. McKay,ab   Louis-Philippe B. Beaulieu,ab   Konstantin A. Udachin,a   André M. Beaucheminb  and  John Paul Pezacki*ab  

* Corresponding authors

a National Research Council of Canada, 100 Sussex Drive, Ottawa, ON, Canada
E-mail: John.Pezacki@nrc-cnrc.gc.ca
Fax: (+)1 613 941 8447

b Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON, Canada

Abstract

Highly strained biarylazacyclooctynone (BARAC) and analogous bioconjugation reagents were shown to undergo novel rearrangement and addition reactions leading to tetracyclic products. This may limit their practical applicability as bioorthogonal reporters for imaging biomolecules within living systems.

Graphical abstract: Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

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Article information

DOI
https://doi.org/10.1039/C3OB40683K
Article type
Communication
Submitted
05 Apr 2013
Accepted
17 Apr 2013
First published
18 Apr 2013

Org. Biomol. Chem., 2013,11, 3436-3441

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Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

M. Chigrinova, C. S. McKay, L. B. Beaulieu, K. A. Udachin, A. M. Beauchemin and J. P. Pezacki, Org. Biomol. Chem., 2013, 11, 3436 DOI: 10.1039/C3OB40683K

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