Conformational and chiral selection of oligonucleotides

Chem Biodivers. 2007 Apr;4(4):803-17. doi: 10.1002/cbdv.200790065.

Abstract

In view of a better understanding of chiral selection of oligonucleotides, we have studied the hybridization of D- and L-CNA (cyclohexane nucleic acids) and D- and L-DNA, with chiral D-beta-homo-DNA and achiral PNA (peptide nucleic acids). PNA hybridizes as well with D-DNA, L-DNA as with D-beta-homo-DNA. The structure of the PNA x D-beta-homo-DNA complex is different from the PNA x DNA duplexes. D-CNA prefers D-DNA as hybridization partner, while L-CNA prefers D-beta-homo-DNA as hybridization partner. The conformation of the enantiomeric oligonucleotides D-CNA and L-CNA in the supramolecular complex with D-DNA and D-beta-homo-DNA, respectively, is different. These data may contribute to the confirmation of a hypothesis of the existence of achiral informative polymers as RNA predecessor, and to the understanding of homochirality of nucleic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Cyclohexanes
  • DNA / chemistry*
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleic Acid Hybridization
  • Oligodeoxyribonucleotides / chemistry
  • Oligonucleotides / chemistry*
  • Selection, Genetic

Substances

  • Cyclohexanes
  • Oligodeoxyribonucleotides
  • Oligonucleotides
  • Cyclohexane
  • DNA