Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Molecules Année : 2024

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Résumé

Abstract Radiolabeled peptides are valuable tools for diagnosis or therapies; they are often radiofluorinated using an indirect approach based on an F-18 prosthetic group. Herein, we are reporting our results on the F-18 radiolabeling of three peptides using two different methods based on click reactions. The first one used the well-known CuAAC reaction, and the second one is based on our recently reported hetero-Diels–Alder (HDA) using a dithioesters (thia-Diels–Alder) reaction. Both methods have been automated, and the 18F-peptides were obtained in similar yields and synthesis time (37–39% decay corrected yields by both methods in 120–140 min). However, to obtain similar yields, the CuAAC needs a large amount of copper along with many additives, while the HDA is a catalyst and metal-free reaction necessitating only an appropriate ratio of water/ethanol. The HDA can therefore be considered as a minimalist method offering easy access to fluorine-18 labeled peptides and making it a valuable additional tool for the indirect and site-specific labeling of peptides or biomolecules.
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hal-04647002 , version 1 (12-07-2024)

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Timothé Maujean, Sridevi M. Ramanoudjame, Stéphanie Riché, Clotilde Le Guen, Frederic Boisson, et al.. Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods. Molecules, 2024, 29 (13), pp.3198. ⟨10.3390/molecules29133198⟩. ⟨hal-04647002⟩
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