Issue 7, 2019

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 nano-structures in aqueous media. However, their structural exploration and screening of self-assembling properties are often limited by time-consuming synthesis and purification steps. We here describe the application of an 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 preparation 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.

Graphical abstract: Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles

Supplementary files

Article information

Article type
Paper
Submitted
11 sept. 2018
Accepted
22 oct. 2018
First published
25 oct. 2018

Org. Biomol. Chem., 2019,17, 1984-1991

Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles

R. Booth, I. Insua, G. Bhak and J. Montenegro, Org. Biomol. Chem., 2019, 17, 1984 DOI: 10.1039/C8OB02243G

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