title: Fluorogenic Behaviour of the Hetero-Diels-Alder Ligation of 5-Alkoxyoxazoles with Maleimides and their Applications.
abstract: Fluorogenic reactions are largely underrepresented in the toolbox of chemoselective ligations despite their tremendous potential, particularly in chemical biology and biochemistry. In this respect, we have investigated in full detail the fluorescence behaviour of the azaphthalamide, a scaffold which is generated through a hetero-Diels-Alder reaction of 5-alkoxyoxazole and maleimide derivatives under mild conditions that are compatible with, among others, peptide chemistry. The scope and limitations of such a fluorogenic labelling strategy were examined through four distinct applications, which target enzymatic activities or bioorthogonal reactions.
authors.affiliation: Normandie University, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000, Rouen, France.
authors.forename: Kévin
authors.initials: K
authors.lastname: Renault
authors.affiliation: Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada.
authors.forename: Laurie-Anne
authors.initials: LA
authors.lastname: Jouanno
authors.affiliation: Normandie University, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000, Rouen, France.
authors.forename: Antoine
authors.initials: A
authors.lastname: Lizzul-Jurse
authors.affiliation: Normandie University, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000, Rouen, France.
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
authors.affiliation: Normandie University, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000, Rouen, France.
authors.forename: Cyrille
authors.identifier: http://orcid.org/0000-0002-5014-7217
authors.initials: C
authors.lastname: Sabot
keywords: Diels-Alder; azaphthalimide; fluorescence spectroscopy; ligation; oxazole