title: A new class of foldamers based on cis-gamma-amino-L-proline.
abstract: A synthetic method for the preparation of conformationally constrained gamma-peptides derived from gamma-amino-L-proline is described. The methodology allows the independent buildup of the peptide backbone and the introduction of sequential variations by reactions with the alpha-amino group of gamma-aminoproline. Both alkyl- and acyl-substituted gamma-peptides have been prepared and studied by CD and NMR. Conformational restrictions due to the cyclic structure of the monomer give rise to long-range interactions that are indicative of secondary structures even in aqueous solution. Interresidue NOEs suggest a concatenation of turns that, in a permissive solvent, could give rise to an isolated hydrogen bond ribbon, flanked and protected by proline rings.
authors.affiliation: Barcelona Biomedical Research Institute, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.
authors.forename: Josep
authors.initials: J
authors.lastname: Farrera-Sinfreu
authors.forename: Laura
authors.initials: L
authors.lastname: Zaccaro
authors.forename: David
authors.initials: D
authors.lastname: Vidal
authors.forename: Xavier
authors.initials: X
authors.lastname: Salvatella
authors.forename: Ernest
authors.initials: E
authors.lastname: Giralt
authors.forename: Miquel
authors.initials: M
authors.lastname: Pons
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Miriam
authors.initials: M
authors.lastname: Royo
mesh_terms: D000613:Aminobutyrates / Q000737:chemistry; D002942:Circular Dichroism; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011487:Protein Conformation; D017510:Protein Folding; D012997:Solvents
chemical_list: D000613:Aminobutyrates; D007202:Indicators and Reagents; D009842:Oligopeptides; D012997:Solvents; C467925:aminoproline; C005959:2,4-diaminobutyric acid; D011392:Proline