Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes.
Fiche publication
Date publication
avril 2018
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr KOLODYCH Sergii
Tous les auteurs :
Taran F, Riomet M, Decuypere E, Porte K, Bernard S, Plougastel L, Kolodych S, Audisio D
Lien Pubmed
Résumé
Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners. This study identified the most relevant substituents which allow to increase the rate of the transformation and to develop a bifunctional cleavable linker with improved kinetics.
Mots clés
cleavable linker, click, iminosydnones, mesoionics, release reactions
Référence
Chemistry. 2018 Apr 17;: