title: Phe-Ala-based diazaspirocyclic lactam as nucleator of type II' β-turn.
abstract: The synthesis of a novel Phe-Ala dipeptide mimic, built up on a diazaspirocyclic lactam core, is presented. This new scaffold was evaluated for conformational mimicry of reverse turn by combining molecular modeling, IR, NMR, and X-ray diffraction experiments. All these tools agree on the presence of a strong intramolecular hydrogen bond, thus demonstrating the ability of this spiro compound to act as a type II' β-turn inducer.
authors.affiliation: Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica 'Giulio Natta', Italy. alessandro.sacchetti@polimi.it
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sacchetti
authors.forename: Alessandra
authors.initials: A
authors.lastname: Silvani
authors.forename: Giordano
authors.initials: G
authors.lastname: Lesma
authors.forename: Tullio
authors.initials: T
authors.lastname: Pilati
mesh_terms: D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D017433:Protein Structure, Secondary; D013055:Spectrophotometry, Infrared; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D004151:Dipeptides; D007769:Lactams; D013141:Spiro Compounds; C039552:phenylalanylalanine