Synthesis of conformationally constrained peptidomimetics using multicomponent reactions

Autor: Scheffelaar, R., Klein Nijenhuis, R.A., Paravidino, M., Lutz, M., Spek, A.L., Ehlers, A.W., de Kanter, F.J.J., Groen, M.B., Orru, R.V.A., Ruijter, E., Crystal and Structural Chemistry, Rontgen participation programme, Sub Crystal and Structural Chemistry
Rok vydání: 2009
Zdroj: Journal of Organic Chemistry, 74(2), 660. American Chemical Society : Division of Carbohydrate Chemistry
ISSN: 0022-3263
Popis: 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.
Databáze: OpenAIRE