Etude méthodologique du couplage d’acides aminés trifluorométhylés et application à la synthèse d’analogues du GPE, un tripeptide à visée thérapeutique

Abstract : GPE is a tripeptide with neuroprotecting activity both in-vitro and in-vivo for various neuronal dammage. The goal of this thesis was to work out peptide coupling methods for trifluoromethylated amino acids and the synthesis of trifluoromethylated analogs of GPE.During this thesis, the synthesis of enantiopure cyclic trifluoromethylated amino acids (proline and pseudoprolines) was performed successfully on grams scale.Then, methodological study of their incorporation in peptide was performed.NMR experiments were made to investigate the cis/trans conformation of the amide bound of trifluoromethylated peptide. At last, analogs of the tripeptide GPE were made with trifluoromethylated proline and pseudoprolines instead of the proline. Biological tests are currently under progress to evaluate their activity on various neuronal disorders.
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Julien Simon. Etude méthodologique du couplage d’acides aminés trifluorométhylés et application à la synthèse d’analogues du GPE, un tripeptide à visée thérapeutique. Autre. Université de Cergy Pontoise, 2012. Français. ⟨NNT : 2012CERG0596⟩. ⟨tel-00816535⟩

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