title: Synthesis and analysis of the conformational preferences of 5-aminomethyloxazolidine-2,4-dione scaffolds: first examples of β(2)- and β(2, 2)-homo-Freidinger lactam analogues.
abstract: Constrained peptidomimetic scaffolds are of considerable interest for the design of therapeutically useful analogues of bioactive peptides. We present the single-step cyclization of (S)- or (R)-α-hydroxy-β(2)- or α-substituted-α-hydroxy-β(2, 2)-amino acids already incorporated within oligopeptides to 5-aminomethyl-oxazolidine-2,4-dione (Amo) rings. These scaffolds can be regarded as unprecedented β(2)- or β(2, 2)-homo-Freidinger lactam analogues, and can be equipped with a proteinogenic side chain at each residue. In a biomimetic environment, Amo rings act as inducers of extended, semi-bent or folded geometries, depending on the relative stereochemistry and the presence of α-substituents.
authors.affiliation: Dept. of Chemistry "G. Ciamician", University of Bologna via Selmi 2, 40126, Bologna (Italy), Fax: (+39) 0512099456.
authors.forename: Arianna
authors.initials: A
authors.lastname: Greco
authors.forename: Sara
authors.initials: S
authors.lastname: Tani
authors.forename: Rossella
authors.initials: R
authors.lastname: De Marco
authors.forename: Luca
authors.initials: L
authors.lastname: Gentilucci
mesh_terms: D003500:Cyclization; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D057786:Peptidomimetics; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D007769:Lactams; D023303:Oxazolidinones; D010455:Peptides; D057786:Peptidomimetics
keywords: Freidinger lactams; amino acids; chain structures; conformation analysis; peptidomimetics