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Synthèse et études structurales de nouveaux 2 : 1-[[alpha]/aza]-oligomères, vers de nouveaux foldamères

Abstract : Foldamers are described as any oligomers with a strong tendency to adopt a specific compact conformation in solution through non covalent interactions. These compounds can make duplexes with RNA and DNA and are more resistant to peptidases. Thus foldamers can have a biological activity. Among azapseudopeptide oligomers, substitution of a nitrogen for the CHa group is a way to preserve the side chains of analogous peptides. This substitution entails the lost of chiral center and the overall conformational and local electronic states might be affected. We have synthesized 2:1-[a/aza]-oligomers on liquid phase. We have developed a new general protocol for obtaining various Boc-azaAA-AA-OMe. Then, 2:1-[a/aza]-trimers, obtained from the precursors, were used in oligomerization reaction by peptidic coupling. By this way, we obtained the first 2:1-[a/aza]-oligomers in very good yields. The structure of the obtained oligomers was analysed by NMR and IR spectroscopies, X-ray diffraction and molecular modelling. The 2:1-[a/aza]-trimers show a ßII-turn and the 2:1-[a/aza]-hexamers structure themselves. On the whole, by NMR and IR spectroscopies, we can strongly consider that our 2:1-[a/aza]-oligomers structure themselves in solution to form foldamers
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Cécile Abbas-Quinternet. Synthèse et études structurales de nouveaux 2 : 1-[[alpha]/aza]-oligomères, vers de nouveaux foldamères. Génie des procédés. Institut National Polytechnique de Lorraine, 2009. Français. ⟨NNT : 2009INPL055N⟩. ⟨tel-01748727⟩



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