Synthesis and conformational studies of peptido-squaramide foldable modules: a new class of turn-mimetic compounds |
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Authors: | Martínez Luis Sampedro Angel Sanna Elena Costa Antoni Rotger Carmen |
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Institution: | Departament de Química, Universitat de les Illes Balears, Crta de Valldemosa km 7.5, Palma, Spain. |
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Abstract: | The β-turn unit is one of the most important secondary structure elements in proteins. The access to new conformationally controlled foldable modules can afford compounds with interesting bioactivities. Here, we describe a new family of peptido-squaramide foldable modules based on the considerable potential of the squaramide unit as a hydrogen bond donor and acceptor as well as the low rotational barrier of the C-N bond. The conformational analysis by NMR of these modules in chloroform and acetonitrile solution shows that a disecondary squaramide with the 4-aminobutyric acid in one of its substituents can mimic the β-turn structure driven by the formation of an intramolecular hydrogen bonded ten-membered ring. This structure, although flexible, has been successfully combined with dipeptide chains to induce the formation of a hairpin-like structure driven by the formation of several cross-strand intramolecular hydrogen bonds. |
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