Gel- and solid-state-structure of dialanine and diphenylalanine amphiphiles

importance of C···H interactions in gelation

Abbas D. Farahani, Adam D. Martin, Hasti Iranmesh, Mohan M. Bhadbhade, Jonathan E. Beves, Pall Thordarson

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

To investigate the role of the capping group in the solution and solid-state self-assembly of short peptide amphiphiles, dialanine and diphenylalanine have been linked via the N-terminus to a benzene (phenyl) and 3-naphthyl capping groups using three different methylene linkers; (CH2)n, n=0–4 for the benzene and 0, 1 and 2 for the naphthalene capping group. Atomic force microscopy (AFM), oscillatory rheology, circular dichroism (CD), and IR analysis have been employed to understand the properties of these peptide-based hydrogels. Several X-ray structures of these short peptide gelators give useful conformational information regarding packing. A comparison of these solid state structures with their gel state properties yielded greater insights into the process of self-assembly in short peptide gelators, particularly in terms of the important role of C···H interactions appear to play in determining if a short aromatic peptide does form a gel or not.
Original languageEnglish
Pages (from-to)972-983
Number of pages12
JournalChemPhysChem
Volume20
Issue number7
Early online date19 Feb 2019
DOIs
Publication statusPublished - 2 Apr 2019
Externally publishedYes

Keywords

  • C⋅⋅⋅H interactions
  • Hirshfeld surface analysis
  • aromatic peptide amphiphiles
  • hydrogels
  • hydrogen bonding

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