Solid-Phase Synthesis of Water-Soluble Helically Folded Hybrid alpha-Amino Acid/Quinoline Oligoamides
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en
Article de revue
Ce document a été publié dans
Journal of Organic Chemistry. 2016, vol. 81, n° 3, p. 1137-1150
Résumé en anglais
We report here a solid phase synthesis methodology that allows the incorporation of alpha-amino acids (X) into quinoline (Q) oligoamide foldamer sequences. Water-soluble hybrid oligoamides based on the XQ(2) trimer repeat ...Lire la suite >
We report here a solid phase synthesis methodology that allows the incorporation of alpha-amino acids (X) into quinoline (Q) oligoamide foldamer sequences. Water-soluble hybrid oligoamides based on the XQ(2) trimer repeat motif were shown to adopt helical conformations presenting alpha-amino acid side chains in a predictable linear array on one face of the helix. In contrast, sequences based on the XQ dimer motif expressed less well-defined behavior, most likely due to local conformational variability precluding long-range order. Also presented is a full structural investigation by NMR of a dodecameric XQ(2)-type foldamer containing four different amino acid residues (Lys, Ala, Asp, and Ser).< Réduire
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