Triazinium Ligation: Bioorthogonal Reaction of N1-Alkyl 1,2,4-Triazinium Salts

0573725 - ÚOCHB 2024 RIV US eng J - Journal Article
Šlachtová, Veronika - Bellová, Simona - La-Venia, A. - Galeta, Juraj - Dračínský, Martin - Chalupský, Karel - Dvořáková, Alexandra - Mertlíková-Kaiserová, Helena - Rukovanský, P. - Dzijak, Rastislav - Vrábel, Milan
Triazinium Ligation: Bioorthogonal Reaction of N1-Alkyl 1,2,4-Triazinium Salts.
Angewandte Chemie - International Edition. Roč. 62, č. 36 (2023), č. článku e202306828. ISSN 1433-7851. E-ISSN 1521-3773
R&D Projects: GA ČR(CZ) GF20-30494L; GA MŠMT(CZ) LX22NPO5104
Institutional support: RVO:61388963
Keywords : bioimaging * click reaction * protein labeling * proteins * triazines
OECD category: Organic chemistry
Impact factor: 16.6, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/anie.202306828

The development of reagents that can selectively react in complex biological media is an important challenge. Here we show that N1-alkylation of 1,2,4-triazines yields the corresponding triazinium salts, which are three orders of magnitude more reactive in reactions with strained alkynes than the parent 1,2,4-triazines. This powerful bioorthogonal ligation enables efficient modification of peptides and proteins. The positively charged N1-alkyl triazinium salts exhibit favorable cell permeability, which makes them superior for intracellular fluorescent labeling applications when compared to analogous 1,2,4,5-tetrazines. Due to their high reactivity, stability, synthetic accessibility and improved water solubility, the new ionic heterodienes represent a valuable addition to the repertoire of existing modern bioorthogonal reagents.
Permanent Link: https://hdl.handle.net/11104/0344107