Work

Solvatochromism and Click Reactivity of Yellow Tetrazines

Year: 2026

Type: article

Abstract: Hydroxypyridyl-substituted 1,2,4,5-tetrazines have recently been developed as advanced scissors for bioorthogonal click-to-release chemistry. In contrast to the otherwise characteristic pink color of 1,2,4,5-tetrazines, these compounds were observed to give yellow solutions in methanol and buffered aqueous media. This study shows that the solvatochromism of hydroxypyridyl-tetrazines has its origin in varying protonation states of the phenolic OH group and reveals the impact of deprotonation on bioorthogonal click reactivity. We demonstrate that the rate of the Diels-Alder cycloaddition is significantly affected by the pH of the aqueous solution, thereby providing critical insights for the development of molecular tools for bioorthogonal bond cleavage.

Source: Bioconjugate Chemistry

DOI: 10.1021/acs.bioconjchem.6c00097

Authors: Patrick Keppel, Jakob Raffler, Hannes Mikula, Dennis Svatunek

Institution: TU Wien

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Technische Universitat Wien, Austrian Science Fund, Technische Universität Wien, HORIZON EUROPE European Research Council