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Issue 39, 2019
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Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

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Abstract

Expanding the scope of bioorthogonal reactivity requires access to new and mutually compatible reagents. We report here that 1,2,4-triazines can be tuned to exhibit unique reaction profiles with biocompatible strained alkenes and alkynes. Computational analyses were used to identify candidate orthogonal reactions, and the predictions were experimentally verified. Notably, 5-substituted triazines, unlike their 6-substituted counterparts, undergo rapid [4 + 2] cycloadditions with a sterically encumbered strained alkyne. This unique, sterically controlled reactivity was exploited for dual bioorthogonal labeling. Mutually orthogonal triazines and cycloaddition chemistries will enable new multi-component imaging applications.

Graphical abstract: Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

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Publication details

The article was received on 22 Mar 2019, accepted on 11 Aug 2019 and first published on 21 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC01427F
Chem. Sci., 2019,10, 9109-9114
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Isomeric triazines exhibit unique profiles of bioorthogonal reactivity

    D. N. Kamber, S. S. Nguyen, F. Liu, J. S. Briggs, H. Shih, R. D. Row, Z. G. Long, K. N. Houk, Y. Liang and J. A. Prescher, Chem. Sci., 2019, 10, 9109
    DOI: 10.1039/C9SC01427F

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