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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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046236
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:37:20 PM
Last modification on : Thursday, July 2, 2020 - 3:29:51 AM

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Kévin Renault, Laurie-Anne Jouanno, Antoine Lizzul-Jurse, Pierre-Yves Renard, Cyrille Sabot. Fluorogenic Behaviour of the Hetero-Diels–Alder Ligation of 5-Alkoxyoxazoles with Maleimides and their Applications. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (51), pp.18522-18531. ⟨10.1002/chem.201603617⟩. ⟨hal-02046236⟩

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