Metal-Ion-Mediated Supramolecular Assembly of C3 -Peptides

Chem Asian J. 2017 Mar 2;12(5):497-502. doi: 10.1002/asia.201601721. Epub 2017 Feb 3.

Abstract

An investigation on a supramolecular assembly of C3 -molecules benzene-1,3,5-tricarboxamides carrying tetrapeptide Gly-Ala-Gly-Ala pendants promoted by hydrogen bonding and metal ion coordination is described. A Gly-Ala peptide sequence was selected as it is the most abundant repeating unit in silkworm silk, and known to form β-sheets through efficient intermolecular hydrogen bonds. These C3 -peptides formed long helical fibers in solvents mainly owing to strong hydrogen bonding. However, in the presence of divalent metal ions, chirality of these helical fibers was enhanced through metal coordination and could be transformed into nanospheres with an excess amount of the ions. Different metal ions show different tendencies to mediate the supramolecular chirality, which can even be inverted according to coordination differences.

Keywords: chirality; hydrogen bonds; metal-ion coordination; peptides; supramolecular assembly.

MeSH terms

  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Ions / chemistry
  • Macromolecular Substances / chemical synthesis
  • Macromolecular Substances / chemistry
  • Metals, Alkaline Earth / chemistry*
  • Metals, Heavy / chemistry*
  • Molecular Structure
  • Oligopeptides / chemistry*

Substances

  • Benzamides
  • Ions
  • Macromolecular Substances
  • Metals, Alkaline Earth
  • Metals, Heavy
  • Oligopeptides
  • benzene-1,3,5-tricarboxamide