Synthesis of conformationally constrained peptidomimetics using multicomponent reactions

R. Scheffelaar, R.A. Klein 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

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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.
Original languageUndefined/Unknown
Pages (from-to)660-668
Number of pages9
JournalJournal of Organic Chemistry
Issue number2
Publication statusPublished - 2009

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