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

Organic & Biomolecular Chemistry Pub Date: 2013-10-28 DOI: 10.1039/C3OB40532J

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, 1H 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.

Graphical abstract: The self-assembly of cystine-bridged γ-peptide-based cyclic peptide–dendron hybrids
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