title: Stacking and stability of RNA duplexes containing fluorobenzene and fluorobenzimidazole nucleosides.
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.
authors.affiliation: Institut für Organische Chemie, Johann Wolfgang Goethe-Universität, Marie Curie Strasse 11, D-60439 Frankfurt am Main, Germany.
authors.forename: J
authors.initials: J
authors.lastname: Parsch
authors.forename: J W
authors.initials: JW
authors.lastname: Engels
mesh_terms: D001562:Benzimidazoles / Q000737:chemistry*; D005464:Fluorobenzenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D009690:Nucleic Acid Conformation; D009943:Organophosphorus Compounds / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D012263:Ribonucleosides / Q000737:chemistry*; D012995:Solubility
chemical_list: D001562:Benzimidazoles; D005464:Fluorobenzenes; D009943:Organophosphorus Compounds; D012263:Ribonucleosides; C434331:phosphoramidite; D012313:RNA