Synthesis and folding preferences of γ-amino acid oligopeptides: Stereochemical control in the formation of a reverse turn and a helix

Article abstract of DOI:10.1016/S0040-4039(99)00860-6

The stereoselective synthesis of α-cinnamyl γ-amino acids and the corresponding oligopeptides is described. Detailed 1D and 2D NMR studies in pyridine-d₅ show that the (αR)-cinnamyl γ-amino acid tetrapeptide adopts a reverse turn structure, while the (αS)-cinnamyl γ-amino acid tetrapeptide adopts a right-handed helical structure.