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Séminaire Chimie ED459

Metal-catalyzed chemistry, peptide synthesis and medicinal chemistry

Dr. Frédéric Bihel (Faculté de Pharmacie / Laboratoire d’Innovation Thérapeutique – UMR 7200 CNRS, Université de Strasbourg)

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Le Jeudi 29 janvier 2015 à 13h45
UM2, Salle de Cours SC-16.01

The last two decades were the witnesses of an exponential growth of metal-catalyzed reactions, leading to a revolution in the construction of C–C or C–N bonds. However, these reactions were mainly dedicated to the building of heterocyclic scaffolds, and were poorly applied to peptide synthesis. This state of fact is mainly due to the harsh conditions used initially with metal-catalysis. Since a few years, our group has investigated the possibility to adapt metal-catalyzed reactions to peptide synthesis in various medicinal chemistry projects. During this seminar, I will show how we applied this strategy to the development of ligands of RFamide peptide GPCRs. Using palladium cross-coupling reactions, we were able to build C–C bonds on resin-bound peptides to obtain new ligands of GPR54, a GPCR involved in hormonal modulation. Using a ruthenium-catalyzed reaction, we were able to synthesize a new class of α, β or γ amino-acids exhibiting a tertiary amine on the side chain. These new amino acids were successfully applied as arginine mimetics leading to an orally-active antagonist of NPFF receptor, able to reverse opioid-induced hyperalgesia.

Scheme 1

Contact local IBMM : Dr. Jean-François Hernandez (dépt. DAPP)


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