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Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes
Author(s) -
Bernard Sabrina,
Audisio Davide,
Riomet Margaux,
Bregant Sarah,
Sallustrau Antoine,
Plougastel Lucie,
Decuypere Elodie,
Gabillet Sandra,
Kumar Ramar Arun,
Elyian Jijy,
Trinh Minh Nguyet,
Koniev Oleksandr,
Wagner Alain,
Kolodych Sergii,
Taran Frédéric
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201708790
Subject(s) - bioorthogonal chemistry , click chemistry , chemistry , combinatorial chemistry , bioconjugation , nanotechnology , materials science
We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.