Molecule of the Month
May 2009
Oligopyrenotides -
Abiotic Foldamers with Nucleic Acid-Like Structural Properties

Oligopyrenotides are composed of achiral, phosphodiester-linked pyrene building blocks and a single chiral 1,2-diaminocyclohexane unit. Oligomers form stable hybrids in aqueous solution. Hybridisation is based on stacking interactions of the pyrene building blocks. Hybrids display salt concentration-dependent, structural polymorphism. They adopt left- or right-handed double helical conformations, depending on the salt concentration.
Oligopyrenotides possess a number of structural attributes typical for DNA and RNA and, therefore, represent potential alternatives to the nucleic acids.

This work was carried out in the group of Prof. Robert Häner.

References:

  • Robert Häner, Florent Samain and Vladimir L. Malinovskii;
    "DNA-Assisted Self-Assembly of Pyrene Foldamers"
    Chem. Eur. J., 15, 5701-5708, (2009); doi:10.1002/chem.200900369.