A New Class of Foldamers Based on cis-γ-Amino-L-proline(714 views) Farrera-Sinfreu J, Zaccaro L, Vidal D, Salvatella X, Giralt E, Pons M, Albericio F, Royo M
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2004 May 19; 126(19): 6048-6057.
Keywords: Conformations, Constraint Theory, Hydrogen Bonds, Nuclear Magnetic Resonance, Solutions, Solvents, Conformational Restrictions, Foldamers, Proline Rings, Secondary Structures, Proteins, C Peptide, Gamma Aminoproline, Unclassified Drug, Aqueous Solution, Article, Chemical Structure, Circular Dichroism, Molecular Interaction, Protein Conformation, Protein Secondary Structure, Aminobutyric Acids, Indicators And Reagents, Isomerism, Magnetic Resonance Spectroscopy, Models, Oligopeptides, Protein Folding, Erratum,
Affiliations: *** IBB - CNR ***
Barcelona Biomed. Research Institute, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Combinatorial Chemistry Unit, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Laboratory of Biomolecular NMR, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain
Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1, 08028-Barcelona, Spain
Ist. di Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, 80134, Naples, Italy
References: Not available.
A New Class of Foldamers Based on cis-γ-Amino-L-proline
A synthetic method for the preparation of conformationally constrained γ-peptides derived from γ-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 γ-amino group of γ-aminoproline. Both alkyl- and acyl-substituted γ-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.
A New Class of Foldamers Based on cis-γ-Amino-L-proline
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