Stacking and stability of RNA duplexes containing fluorobenzene and fluorobenzimidazole nucleosides

Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):815-8. doi: 10.1081/NCN-100002436.

Abstract

Six different fluorobenzene or fluorobenzimidazole ribonucleosides and one abasic site were incorporated in oligoribonucleotides. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene.fluorobenzimidazole-modified base pairs a duplex stabilizing force was found that points to a weak F...H hydrogen bond. The lipophilicity of the unprotected nucleosides were investigated by determination of 1-octanol water partition coefficients.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • Fluorobenzenes / chemistry*
  • Hydrogen Bonding
  • Nucleic Acid Conformation
  • Organophosphorus Compounds / chemistry
  • RNA / chemistry*
  • Ribonucleosides / chemistry*
  • Solubility

Substances

  • Benzimidazoles
  • Fluorobenzenes
  • Organophosphorus Compounds
  • Ribonucleosides
  • phosphoramidite
  • RNA