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Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes
Author(s) -
Riomet Margaux,
Decuypere Elodie,
Porte Karine,
Bernard Sabrina,
Plougastel Lucie,
Kolodych Sergii,
Audisio Davide,
Taran Frédéric
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801163
Subject(s) - bioorthogonal chemistry , bifunctional , click chemistry , reactivity (psychology) , chemistry , combinatorial chemistry , linker , alkyne , chemical transformation , kinetics , fragmentation (computing) , chemical biology , computer science , organic chemistry , catalysis , biochemistry , medicine , physics , alternative medicine , pathology , quantum mechanics , operating system
Abstract 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.