Le motif N-aminoamide pour la synthèse d'oligomères linéaires et cycliques ; étude de son impact conformationnel

Abstract : This work describes the synthesis and the structural study of linear and cyclic mixed oligomers alternating N-aminoamide and amide bonds, named 1:1-[a/a-N-amino]mers. The first chapter is a bibliographic study on cyclization methods of peptides and pseudopeptides (backbone modified peptides) and their applications. It has been described that the incorporation of potential structural elements, like introduction of changes to peptide backbone, could be facilitating the cyclization of linear oligomers. With this in mind, the use of previous work in our laboratory, discussed in the second chapter, gives access to new phtaloylated 1:1-[a/a-N-amino]mers and also to the first protected cyclo-1:1-[a/a-N-amino]mers. The deprotection of phthalimid group of one of these cyclic compounds opens up new opportunities like functionalization of the deprotected nitrogen atom. The third chapter sums up the results of the structural analyses and principally highlights the original conformations adopted by these different oligomers and the influence of the N-aminoamide bond. The structures were established through a complete study using several spectroscopic techniques (NMR, IR, fluorescence, X-ray crystallography). For example, the X ray studies highlight the formation of nanotubes through an original self-assembling of deprotected cyclotetramers.
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Maxime Pedeutour. Le motif N-aminoamide pour la synthèse d'oligomères linéaires et cycliques ; étude de son impact conformationnel. Alimentation et Nutrition. Université de Lorraine, 2014. Français. ⟨NNT : 2014LORR0090⟩. ⟨tel-01750813⟩

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