Self-Assembled Micro-Fibres by Oxime Connection of Linear Peptide Amphiphiles

Abstract

Linear peptide amphiphiles are excellent biocompatible scaffolds for the hierarchical self-assembly of one dimensional nanostructures in aqueous media. However, their structural exploration and screening of self-assembling properties is often limited by time-consuming synthesis and purification steps. We here describe the application of the oxime bond as a powerful synthetic tool towards the conjugation of peptide heads bearing a hydroxylamine group with hydrophobic aldehyde tails. This methodology allowed the quick prepraration of a small library of oxime-connected peptide amphiphiles, whose supramolecular screening revealed nano-to-micro fibrillation with dependency on their chemical structure. These results demonstrate the simplicity and the synthetic potential of the oxime conjugation for the preparation of peptide amphiphiles with improved self-assembling capabilities