The self-assembly of cystine-bridged γ-peptide-based cyclic peptide-dendron hybrids

Org Biomol Chem. 2013 Dec 28;11(48):8443-51. doi: 10.1039/c3ob40532j. Epub 2013 Nov 7.

Abstract

Novel cystine-bridged γ-peptide-based cyclic peptide-dendron hybrids have been synthesized by oxidative coupling between two cysteine residues of the linear peptides via the formation of disulfide bonds in high yields. The self-assembly of the hybrids was studied by FT-IR, (1)H NMR, TEM, and AFM analyses which indicate that the nanotube was constructed through intermolecular hydrogen-bonding of the hydrophobic cyclic peptide moieties and possesses amphiphilic property by conjugating a hydrophilic dendron on the exterior of the cyclic peptide ring. The diameters of nanofibers that consisted of nanotubes depend on the employed solvent in the self-assembly process, and uniform filaments formed from double amphiphilic nanotubes via hydrophobic interactions between their hydrophobic faces have been observed in water as well as in aqueous solutions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry*
  • Cystine / chemistry*
  • Disulfides / chemistry
  • Hydrophobic and Hydrophilic Interactions
  • Models, Molecular
  • Nanofibers / chemistry
  • Nanofibers / ultrastructure
  • Nanotubes / chemistry
  • Nanotubes / ultrastructure
  • Peptides, Cyclic / chemistry*

Substances

  • Anthracenes
  • Disulfides
  • Peptides, Cyclic
  • dendron
  • Cystine