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Issue 20, 2020
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Maleimide-based metal-free ligation with dienes: a comparative study

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Abstract

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.

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

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Supplementary files

Article information


Submitted
24 Feb 2020
Accepted
12 Mar 2020
First published
12 Mar 2020

Org. Biomol. Chem., 2020,18, 3874-3887
Article type
Paper

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

A. Lossouarn, K. Renault, L. Bailly, A. Frisby, P. Le Nahenec-Martel, P. Renard and C. Sabot, Org. Biomol. Chem., 2020, 18, 3874
DOI: 10.1039/D0OB00403K

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