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1: J Am Chem Soc. 2004 May 19;126(19):6048-57.Click here to read Links
Erratum in:
J Am Chem Soc. 2005 Jan 12;127(1):474.

A new class of foldamers based on cis-gamma-amino-L-proline.

Farrera-Sinfreu J, Zaccaro L, Vidal D, Salvatella X, Giralt E, Pons M, Albericio F, Royo M.

Barcelona Biomedical Research Institute, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.

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.

PMID: 15137770 [PubMed - indexed for MEDLINE]