1. Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes
- Author
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Karine Porte, Margaux Riomet, Sabrina Bernard, Davide Audisio, Elodie Decuypere, Lucie Plougastel, Sergii Kolodych, and Frédéric Taran
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Biomolecule ,Organic Chemistry ,Kinetics ,Chemical biology ,Alkyne ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Catalysis ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Fragmentation (mass spectrometry) ,Cleavable linker ,Bioorthogonal chemistry ,Bifunctional - 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.
- Published
- 2018