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Issue 7, 2019
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Self-assembled micro-fibres by oxime connection of linear peptide amphiphiles

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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

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Supplementary files

Article information


Submitted
11 Sep 2018
Accepted
22 Oct 2018
First published
25 Oct 2018

Org. Biomol. Chem., 2019,17, 1984-1991
Article type
Paper

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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