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

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.
Original languageUndefined/Unknown
Pages (from-to)660-668
Number of pages9
JournalJournal of Organic Chemistry
Volume74
Issue number2
Publication statusPublished - 2009

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