Recipe for β-sheets: Foldamers containing amyloidogenic peptide sequences

摘要

This paper describes a new class of macrocyclic peptides that fold to form β-sheet structures. These macrocyclic β-sheets consist of a peptide sequence strand linked through two δ-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 β-peptide, tau protein, the B-chain of insulin, and human prion protein fold to form β-sheet structures.