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Foldamères d’oligoamides aromatiques pour le développement de structures secondaires bio-inspirées

Abstract : To mimic the particular folding of the biomolecules’ three-dimensional structures, chemists have developed artificial oligomers that fold into a compact and well-defined structures in solution: foldamers. Nevertheless, the variety of isolated secondary structures of foldamers is not equal to those of biomolecules. The association of different sequences of aromatic oligoamide having distinct secondary structures allowed the development of well-defined helix-sheet-helix architectures in which subcomponents conserve their respective integrity. These unique basket-like objects possess an open-window within the foldamer backbone in which a molecular guest can be accommodate. As a proof of concept, guest binding to one of these structures was found to be fast on the NMR time scale. Then, the development of oligoamide aromatic strands made of monomer encoding for low curvature has allowed to obtain double helices structures. These self-assembled structures showing high molecular weights present a nanometer scale diameter. Eventually, these oligomeric strands were coupled to artificial turn units to obtain β-barrels-like architectures having a large polar cavity. These approaches open the access to the design of ever more complex molecular objects beyond the chemistry of biomolecules.
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Arthur Lamouroux. Foldamères d’oligoamides aromatiques pour le développement de structures secondaires bio-inspirées. Chimie organique. Université de Bordeaux, 2018. Français. ⟨NNT : 2018BORD0421⟩. ⟨tel-02125302⟩

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