The Biological Stability of β-Peptides: No Interactions between α- and β-Peptidic Structures?

Abstract

The use of peptides in pharmaceutical applications is always hindered by the rapid degradation of the peptides by enzymes. Recent work on β-peptides, peptides constructed entirely from β-amino acids, has shown that even the short-chain oligomers (6 or 7 residues) exhibit remarkably stable secondary structures. However, before certain applications of β-peptides can be considered, an information about their possible interactions or reactions with enzymes must be acquired.
Ames tests (all negative) have now been performed on a selection of β-amino acids, which would be the result of the enzymatic degradation of a β-peptide. Furthermore, digestion experiments using a variety of peptidases and β-peptides have now shown that β-peptides, in sharp contrast to their α-peptide counterparts, undergo no degradation.