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

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 var...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2017-05, Vol.8 (5), p.3593-3598
Main Authors: Siegl, Sebastian J, Dzijak, Rastislav, Vázquez, Arcadio, Pohl, Radek, Vrabel, Milan
Format: Article
Language:English
Subjects:
Cationic
Compartments
Diels-Alder reactions
Dienes
Fluorescence
Inverse
Labels
Utilities
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Summary: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 -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 -cyclooctenes and can be used for fluorogenic labeling of subcellular compartments in live cells.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc05442k