6533b7dafe1ef96bd126eb43
RESEARCH PRODUCT
Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation.
Hélène CastelNawal SekkatPierre-yves RenardArnaud ChevalierAnthony RomieuAnthony RomieuCyrille SabotNicolas PerzoNorbert LangeLaurie-anne Jouannosubject
[CHIM.THER]Chemical Sciences/Medicinal ChemistryLigandsCatalysis[CHIM.ANAL]Chemical Sciences/Analytical chemistryFluorescence Resonance Energy TransferOrganic chemistryNuclear Magnetic Resonance BiomolecularOxazoleschemistry.chemical_classificationBioconjugationCycloaddition ReactionMolecular Structure[CHIM.ORGA]Chemical Sciences/Organic chemistryChemistryBiomoleculeOrganic Chemistry[CHIM.CATA]Chemical Sciences/CatalysisFluorescenceUrokinase-Type Plasminogen ActivatorCycloaddition[CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistryEnzyme ActivationFörster resonance energy transferLigationPlasminogen activator[CHIM.CHEM]Chemical Sciences/CheminformaticsConjugatedescription
International audience; 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-01-01 | The Journal of organic chemistry |