Recipe for -Sheets: Foldamers Containing Amyloidogenic Peptide Sequences

This paper describes a new class of macrocyclic peptides that fold to form -sheet structures. These macrocyclic -sheets consist of a peptide sequence strand linked through two -linked ornithine turn units to a peptide template strand containing a single N-methyl amino acid. The macrocycles were readily prepared from commercially available amino acids by solid-phase peptide synthesis followed by solution-phase cyclization. 1H NMR spectroscopic studies showed that macrocycles containing amyloidgenic pentapeptide sequences from amyloid -peptide, tau protein, the B-chain of insulin, and human prion protein fold to form -sheet structures.