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Issue 5, 2017
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The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

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Abstract

1,2,4-Triazines have recently been identified as versatile dienes participating in the inverse electron-demand Diels–Alder reaction with strained dienophiles. However, their widespread utility in bioconjugation reactions is still limited. Herein, we report a systematic study on the reactivity of various 1,2,4-triazines with trans-cyclooctenes showing that the structure of both the triazine and the dienophile significantly affect the reaction rate. Our kinetic study led to the discovery of novel cationic 1,2,4-triazines with superior properties for bioconjugation reactions. We have developed an efficient method that enables their late-stage functionalization and allows for easy access to various useful heterobifunctional scaffolds. In addition, these charged dienes form unprecedented fluorescent products upon reaction with trans-cyclooctenes and can be used for fluorogenic labeling of subcellular compartments in live cells.

Graphical abstract: The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

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Publication details

The article was received on 13 Dec 2016, accepted on 01 Mar 2017 and first published on 01 Mar 2017


Article type: Edge Article
DOI: 10.1039/C6SC05442K
Citation: Chem. Sci., 2017,8, 3593-3598
  • Open access: Creative Commons BY license
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    The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

    S. J. Siegl, R. Dzijak, A. Vázquez, R. Pohl and M. Vrabel, Chem. Sci., 2017, 8, 3593
    DOI: 10.1039/C6SC05442K

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