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

Šlachtová, Veronika; Bellová, Simona; La-Venia, A.; Galeta, Juraj; Dračínský, Martin; Chalupský, Karel; Dvořáková, Alexandra; Mertlíková-Kaiserová, Helena; Rukovanský, P.; Dzijak, Rastislav; Vrábel, Milan

doi:https://dx.doi.org/10.1002/anie.202306828

Number of the records: 1

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

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SYSNO ASEP	0573725
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Triazinium Ligation: Bioorthogonal Reaction of N1-Alkyl 1,2,4-Triazinium Salts
Author(s)	Šlachtová, Veronika (UOCHB-X)_ORCID Bellová, Simona (UOCHB-X) La-Venia, A. (AR) Galeta, Juraj (UOCHB-X)_ORCID Dračínský, Martin (UOCHB-X)_{RID, ORCID} Chalupský, Karel (UOCHB-X) Dvořáková, Alexandra (UOCHB-X) Mertlíková-Kaiserová, Helena (UOCHB-X)_{RID, ORCID} Rukovanský, P. (CZ) Dzijak, Rastislav (UOCHB-X)_ORCID Vrábel, Milan (UOCHB-X)_{RID, ORCID}
Article number	e202306828
Source Title	Angewandte Chemie - International Edition. - : Wiley - ISSN 1433-7851 Roč. 62, č. 36 (2023)
Number of pages	10 s.
Language	eng - English
Country	US - United States
Keywords	bioimaging ; click reaction ; protein labeling ; proteins ; triazines
OECD category	Organic chemistry
R&D Projects	GF20-30494L GA ČR - Czech Science Foundation (CSF)
	LX22NPO5104 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
Method of publishing	Open access
Institutional support	UOCHB-X - RVO:61388963
UT WOS	001034089600001
EID SCOPUS	85165440095
DOI	10.1002/anie.202306828
Annotation	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.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
Year of Publishing	2024
Electronic address	https://doi.org/10.1002/anie.202306828

Number of the records: 1