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La [delta]-azaproline: impact conformationnel de son incorporatrion dans des pseudopeptides

Abstract : This work describes the incoporation the [delta]-azaproline in pseudopeptides for conformational analysis and biological applications. The first chapter of this thesis is devoted to the development of a new substrate of the type Suc Ala X [delta]azaPro Phe [rho] NA (where X is an amino acid) able to measure the catalytic activity of PPIases. These enzymes have shown great interests in the prevention of transplant rejection and in the treatment of Alzheimer's disease because they can interconvert the cis and trans isomers of X-Pro peptidic bond. The second section describes the incorporation of the [delta]-azaproline into pseudotripeptides in which the reactivity of both nitrogen atoms of this surrogate was investigated. It could be demonstrated in particular that the supplementary nitrogen atom of azaproline is much more reactive than the native one because of the steric hindrance generated by the Boc protecting group and the spontaneous oxidation of the CH[alpha] NH[delta] bond represent a huge problem in the peptidic coupling. Finally, the last part of this thesis is dedicated to the conformational analysis of pseudotripeptides. These analyzes are designed to determine the influence of a supplementary nitrogen atom, in [delta] position into proline’s cycle, which can be free or protected by a cluttered group on the conformation of the X-[psy]Pro bond. Spectroscopic techniques such as NMR and IR enabled to demonstrate that steric hindrance generated by a Boc group on [delta] position with the side chain of amino acid upstream this surrogate promotes cis conformation by formation of a ten-membered ring
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Submitted on : Thursday, March 29, 2018 - 1:13:24 PM
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Lucie Flauder. La [delta]-azaproline: impact conformationnel de son incorporatrion dans des pseudopeptides. Alimentation et Nutrition. Université de Lorraine, 2014. Français. ⟨NNT : 2014LORR0241⟩. ⟨tel-01751256⟩



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