Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

Article abstract of DOI:10.1016/S0040-4039(97)00612-6

The incorporation of α-substituted β-amino acids into a tetrapeptide motif induces a reverse rum in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an α-phenylseleno β-amino acid unit within the tetrapeptide.