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Updated: Dec 23, 2025

Harnessing the Bioorthogonal Inverse Electron Demand Diels-Alder Cycloaddition for Pretargeted PET Imaging
Published on: February 3, 2015
Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles
Jordi Agramunt1, Rebecca Ginesi1, Enrique Pedroso1,2
1Departament de Quı́mica Inorgànica i Orgànica (Secció de Quı́mica Orgànica), Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.
Abstract:
Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, d-biotin, BODIPY, or N-acetyl-d-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 °C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
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