title: Synthesis of conformationally constrained peptidomimetics using multicomponent reactions.
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 beta-turn-like structure, the X-ray crystal structure and NMR studies indicate an open turn structure.
authors.affiliation: Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
authors.forename: Rachel
authors.initials: R
authors.lastname: Scheffelaar
authors.forename: Roel A Klein
authors.initials: RA
authors.lastname: Nijenhuis
authors.forename: Monica
authors.initials: M
authors.lastname: Paravidino
authors.forename: Martin
authors.initials: M
authors.lastname: Lutz
authors.forename: Anthony L
authors.initials: AL
authors.lastname: Spek
authors.forename: Andreas W
authors.initials: AW
authors.lastname: Ehlers
authors.forename: Frans J J
authors.initials: FJ
authors.lastname: de Kanter
authors.forename: Marinus B
authors.initials: MB
authors.lastname: Groen
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry*; D013696:Temperature
chemical_list: D010455:Peptides