Synthesis of Conformationally Constrained Peptidomimetics using Multicomponent Reactions

R. Scheffelaar, R.A.K. Nijenhuis, M. Paravidino, M. Lutz, A.L Spek, A.W. Ehlers, F.J.J. de Kanter, M.B. Groen, R.V.A. Orru, E. Ruijter

    Research output: Contribution to JournalArticleAcademicpeer-review

    Abstract

    A novel modular synthetic approach toward constrained peptidomimetics is reported. The approach involves a highly efficient three-step sequence including two multicomponent reactions, thus allowing unprecedented diversification of both the peptide moieties and the turn-inducing scaffold. The turn-inducing properties of the dihydropyridone scaffold were evaluated by molecular modeling, X-ray crystallography, and NMR studies of a resulting peptidomimetic. Although modeling studies point toward a type IV β-turn-like structure, the X-ray crystal structure and NMR studies indicate an open turn structure. © 2009 American Chemical Society.
    Original languageEnglish
    Pages (from-to)660-668
    JournalJournal of Organic Chemistry
    Volume74
    Issue number2
    DOIs
    Publication statusPublished - 2009

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