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 language | English |
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Pages (from-to) | 660-668 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2009 |
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CCDC 720213: Experimental Crystal Structure Determination
Scheffelaar, R. (Contributor), Nijenhuis, R. A. K. (Contributor), Paravidino, M. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), Ehlers, A. W. (Contributor), De Kanter, F. J. J. (Contributor), Groen, M. B. (Contributor), Orru, R. V. A. (Contributor) & Ruijter, E. (Contributor), Unknown Publisher, 1 Jan 2009
DOI: 10.5517/ccs5fp1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccs5fp1&sid=DataCite
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