0475538 - ÚOCHB 2018 RIV GB eng J - Journal Article
Siegl, Sebastian J. - Dzijak, Rastislav - Vázquez, Arcadio - Pohl, Radek - Vrábel, Milan
The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions.
Chemical Science. Roč. 8, č. 5 (2017), s. 3593-3598. ISSN 2041-6520. E-ISSN 2041-6539
R&D Projects: GA ČR GJ15-06020Y
Institutional support: RVO:61388963
Keywords : Diels-Alder reactions * trans-cyclooctene ligation * living cells
OECD category: Organic chemistry
Impact factor: 9.063, year: 2017
http://pubs.rsc.org/en/content/articlehtml/2017/sc/c6sc05442k

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.
Permanent Link: http://hdl.handle.net/11104/0272222