Oxazolopiperidin-2-ones as type II' beta-turn mimetics: synthesis and conformational analysis |
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Authors: | Estiarte M A Rubiralta M Diez A Thormann M Giralt E |
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Institution: | Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 08028-Barcelona, Spain. |
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Abstract: | We describe a straightforward synthesis of 9-substituted 3-aminooxazolidinopiperidin-2-ones 4. Some derivatives were prepared for use in peptide synthesis as rigidified surrogates of the Ala-Pro dipeptide. Analysis of the amide derivatives 14 by NMR experiments and molecular mechanics/dynamics calculations shows that the major isomer 14a has a stronger propensity than the minor isomer 14b to adopt beta-turn conformations, and the calculations indicate that in water 14a adopts a stable betaII' turn conformation. |
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