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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2020

Maleimide-based metal-free ligation with dienes: a comparative study

Résumé

A brief literature survey reveals that metal-free ligation such as the maleimide-based cycloaddition with electron-rich (hetero)dienes is a widespread tool for the assembly of (bio)molecular systems with applications in biotechnology, materials science, polymers and bio-organic chemistry. Despite their everyday use, only scattered data about their kinetics as well as the stabilities of corresponding products under physiological conditions, are accessible. These key parameters are yet, of paramount importance to ensure the rapid and effective preparation of stable compounds. Herein is reported a systematic study regarding the different classes of dienes used in chemoselective ligation, including their accessibility and stability, as well as comparative kinetic experiments and products stability assays. We took advantage of these data to develop a double labeling strategy from the combined use of cyclopentadiene and oxazole dienes.

Domaines

Chimie organique
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Dates et versions

hal-03010566 , version 1 (17-11-2020)

Identifiants

Citer

Alexis Lossouarn, Kévin Renault, Laëtitia Bailly, Axel Frisby, Patricia Le Nahenec-Martel, et al.. Maleimide-based metal-free ligation with dienes: a comparative study. Organic & Biomolecular Chemistry, 2020, 18 (20), pp.3874-3887. ⟨10.1039/D0OB00403K⟩. ⟨hal-03010566⟩
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