Synthesis and stability of collagen mimetic peptides featuring δ-heteroatom-substituted prolines

Abstract

We describe the first investigation of collagen mimetic peptides harboring proline surrogates with heteroatoms at the δ-position. While dehydro-δ-azaproline and (N-methyl)-δ-azaproline destabilized the parent structure, replacement of the Xaa proline residue with δ-oxaproline resulted in a faster-folding collagen mimetic peptide with equivalent thermal stability.