Poster Presentation 6th Modern Solid Phase Peptide Synthesis & Its Applications Symposium 2017

Cyclic peptides: Building blocks for novel nanotubes (#51)

Jo Sampson 1 , Mitchell R Silk 1 , Philip E Thompson 1 , David K Chalmers 1
  1. Monash Institute of Pharmaceutical Sciences, Melbourne, VICTORIA, Australia

Cyclic peptides (CPs) with alternating D and L amino acids assemble to form nanotubes through a regular, antiparallel β-sheet hydrogen-bonding network. This favourable conformation results in the pseudo-equatorial projection of the amino acid residues, allowing ionic or covalent bonding to occur between successive layers. Historically, homogeneous nanotubes of indeterminate length have been synthesised and side chain interactions have not been fully exploited for nanotube construction.

As such, this project aims to synthesise nanotubes of specific length and long range order, by tethering adjacent CPs through the side chain residues using accessible chemical methods. To date, a range of CPs have been synthesised and used as building blocks to obtain nanotubes of different lengths, including dimers and tetramers. Both homogeneous and heterogeneous structures have been synthesised, providing a method of obtaining highly complex nanomaterials with handles for further functionalisation.

  1. Ghadiri et al, Nature, 1993, 366, 324-327
  2. Silk et al, Chem Commun, 2017, 53, 6613-6616