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Article Dans Une Revue Journal of Organic Chemistry Année : 2014

Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation

Résumé

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.
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Dates et versions

hal-01144842 , version 1 (22-04-2015)

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Laurie-Anne Jouanno, Arnaud Chevalier, Nawal Sekkat, Nicolas Perzo, Hélène Castel, et al.. Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation. Journal of Organic Chemistry, 2014, 79 (21), pp.10353-10366. ⟨10.1021/jo501972m⟩. ⟨hal-01144842⟩
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