Hierarchical Self-Assembly of Histidine-Functionalized Peptide Amphiphiles into Supramolecular Chiral Nanostructures

Meryem Hatip Koc, Goksu Cinar Ciftci, Sefer Baday, Valeria Castelletto, Ian W. Hamley, Mustafa O. Guler*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

Controlling the hierarchical organization of self-assembling peptide amphiphiles into supramolecular nanostructures opens up the possibility of developing biocompatible functional supramolecular materials for various applications. In this study, we show that the hierarchical self-assembly of histidine- (His-) functionalized PAs containing d- or l-amino acids can be controlled by both solution pH and molecular chirality of the building blocks. An increase in solution pH resulted in the structural transition of the His-functionalized chiral PA assemblies from nanosheets to completely closed nanotubes through an enhanced hydrogen-bonding capacity and π-π stacking of imidazole ring. The effects of the stereochemistry and amino acid sequence of the PA backbone on the supramolecular organization were also analyzed by CD, TEM, SAXS, and molecular dynamics simulations. In addition, an investigation of chiral mixtures revealed the differences between the hydrogen-bonding capacities and noncovalent interactions of PAs with d- and l-amino acids.

Original languageEnglish
Pages (from-to)7947-7956
Number of pages10
JournalLangmuir
Volume33
Issue number32
DOIs
Publication statusPublished - 15 Aug 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

Funding

FundersFunder number
Engineering and Physical Sciences Research CouncilEP/L020599/1

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