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Synthèse et étude conformationnelle d’[alpha]-hydrazinopeptides linéaires et cycliques

Abstract : The formation of nanostructures with well-defined organic brick self-assembly has received much attention due to their potential applications in chemistry and biology. Among all these organic elements, peptides and pseudopeptides are among the most promising because of their similarity to proteins. We can enumerate many peptides self-assembly, such as nanotubes, nonafibres, vesicles, nanospheres etc … In this context, we are interested by the synthesis and overall structural study of hydrazinopeptides. Thanks to the additional nitrogen, these bis-nitrogen pseudopeptides are able to self-assemble into new structuring. The 1:1[alpha/alpha-Nalpha-Bn-hydrazino] linear peptides showed coalesce into hydrazinoturn and gamma-turn in solution. We have highlighted the ability of analogues of 1:1[ß/alpha-Nalpha-Bn-hydrazino] linear peptides to be structured in hydrazinoturn only, in solution. Similarly, we have demonstrated the ability of pure alpha-Nalpha-Bn-hydrazino pseudopeptides to be structured in a very solid solution structure formed of hydrazinoturn observable also in crystal state. Secondly, and as part of the development of nanotube structures, we have studied a serie of 1:1[alpha/alpha-Nalpha-hydrazino] cyclic peptides, and especially cyclotetrameres. In this context, we have sought to highlight the various parameters that may affect the organization in nanotubes, in order to develop the best strategy to achieve this potential application in nanostructuring views. The various parameters studied are: the synthetic strategy, the chirality, the orientation of side chains, and finally the ability to form gels
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Eugénie Romero. Synthèse et étude conformationnelle d’[alpha]-hydrazinopeptides linéaires et cycliques. Alimentation et Nutrition. Université de Lorraine, 2015. Français. ⟨NNT : 2015LORR0232⟩. ⟨tel-01754492⟩

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