Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 34, Pages 8535-8541Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801163
Keywords
cleavable linker; click; iminosydnones; mesoionics; release reactions
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Funding
- French Research National Agency [ANR-14-CE06-0004]
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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.
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