title: 2'-Fluoro substituents can mimic native 2'-hydroxyls within structured RNA.
abstract: The ability of fluorine in a C-F bond to act as a hydrogen bond acceptor is controversial. To test such ability in complex RNA macromolecules, we have replaced native 2'-OH groups with 2'-F and 2'-H groups in two related systems, the Tetrahymena group I ribozyme and the ΔC209 P4-P6 RNA domain. In three cases the introduced 2'-F mimics the native 2'-OH group, suggesting that the fluorine atom can accept a hydrogen bond. In each of these cases the native hydroxyl group interacts with a purine exocyclic amine. Our results give insight about the properties of organofluorine and suggest a possible general biochemical signature for tertiary interactions between 2'-hydroxyl groups and exocyclic amino groups within RNA.
authors.affiliation: Department of Biochemistry, Stanford University, Stanford, CA 94305, USA.
authors.forename: Marcello
authors.initials: M
authors.lastname: Forconi
authors.forename: Jason P
authors.initials: JP
authors.lastname: Schwans
authors.forename: Rishi H
authors.initials: RH
authors.lastname: Porecha
authors.forename: Raghuvir N
authors.initials: RN
authors.lastname: Sengupta
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Piccirilli
authors.forename: Daniel
authors.initials: D
authors.lastname: Herschlag
mesh_terms: D005461:Fluorine / Q000737:chemistry*; D006860:Hydrogen Bonding; D017665:Hydroxyl Radical / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D011687:Purines / Q000737:chemistry; D012313:RNA / Q000737:chemistry*; D016337:RNA, Catalytic / Q000737:chemistry*; D013768:Tetrahymena / Q000737:chemistry*
chemical_list: C116167:GIR1 ribozyme; D011687:Purines; D016337:RNA, Catalytic; D005461:Fluorine; D017665:Hydroxyl Radical; D012313:RNA; C030985:purine