title: Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation.
abstract: Diversification of existing chemoselective ligations is required to efficiently access complex and well-defined biomolecular assemblies with unique and valuable properties. The development and bioconjugation applications of a novel Diels-Alder-based irreversible site-specific ligation are reported. The strategy is based on a Kondrat'eva cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles and maleimides that readily react together under mild and easily tunable reaction conditions to afford a fully stable pyridine scaffold. The potential of this novel bioconjugation is demonstrated through the preparation of fluorescent conjugates of biomolecules and a novel Förster resonance energy transfer (FRET)-based probe suitable for the in vivo detection and imaging of urokinase-like plasminogen activator (uPA), which is a key protease involved in cancer invasion and metastasis.
authors.affiliation: Normandie Univ, COBRA, UMR 6014 & FR 3038; Univ Rouen; INSA Rouen; CNRS , 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Laurie-Anne
authors.initials: LA
authors.lastname: Jouanno
authors.forename: Arnaud
authors.initials: A
authors.lastname: Chevalier
authors.forename: Nawal
authors.initials: N
authors.lastname: Sekkat
authors.forename: Nicolas
authors.initials: N
authors.lastname: Perzo
authors.forename: Hélène
authors.initials: H
authors.lastname: Castel
authors.forename: Anthony
authors.initials: A
authors.lastname: Romieu
authors.forename: Norbert
authors.initials: N
authors.lastname: Lange
authors.forename: Cyrille
authors.initials: C
authors.lastname: Sabot
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D004789:Enzyme Activation; D031541:Fluorescence Resonance Energy Transfer; D008024:Ligands; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000737:chemistry*; D014568:Urokinase-Type Plasminogen Activator / Q000737:chemistry*
chemical_list: D008024:Ligands; D010080:Oxazoles; D014568:Urokinase-Type Plasminogen Activator