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- Title
Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes.
- Authors
Riomet, Margaux; Decuypere, Elodie; Porte, Karine; Bernard, Sabrina; Plougastel, Lucie; Kolodych, Sergii; Audisio, Davide; Taran, Frédéric
- Abstract
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.
- Subjects
SYDNONES; AROMATIC compound synthesis; CHEMICAL biology; ALKYNE synthesis; BIOMOLECULE analysis
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 34, p8535
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201801163