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 journalArticleResearchpeer-review

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.
LanguageEnglish
Pages972-983
Number of pages12
JournalChemPhysChem
Volume20
Issue number7
Early online date19 Feb 2019
DOIs
Publication statusPublished - 2 Apr 2019
Externally publishedYes

Fingerprint

Amphiphiles
gelation
Gelation
peptides
Gels
gels
solid state
Peptides
Benzene
Self assembly
interactions
self assembly
benzene
Hydrogels
Rheology
rheology
naphthalene
methylene
dichroism
Atomic force microscopy

Keywords

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

Cite this

Farahani, Abbas D. ; Martin, Adam D. ; Iranmesh, Hasti ; Bhadbhade, Mohan M. ; Beves, Jonathan E. ; Thordarson, Pall. / Gel- and solid-state-structure of dialanine and diphenylalanine amphiphiles : importance of C···H interactions in gelation. In: ChemPhysChem. 2019 ; Vol. 20, No. 7. pp. 972-983.
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Gel- and solid-state-structure of dialanine and diphenylalanine amphiphiles : importance of C···H interactions in gelation. / Farahani, Abbas D.; Martin, Adam D.; Iranmesh, Hasti; Bhadbhade, Mohan M.; Beves, Jonathan E.; Thordarson, Pall.

In: ChemPhysChem, Vol. 20, No. 7, 02.04.2019, p. 972-983.

Research output: Contribution to journalArticleResearchpeer-review

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