Forconi Marcello, Schwans Jason P, Porecha Rishi H, Sengupta Raghuvir N, Piccirilli Joseph A, Herschlag Daniel
Department of Biochemistry, Stanford University, Stanford, CA 94305, USA.
Chem Biol. 2011 Aug 26;18(8):949-54. doi: 10.1016/j.chembiol.2011.07.014.
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.
碳氟键中的氟作为氢键受体的能力存在争议。为了在复杂的RNA大分子中测试这种能力，我们在两个相关系统——嗜热四膜虫I组核酶和ΔC209 P4-P6 RNA结构域中，将天然的2'-羟基用2'-氟和2'-氢取代。在三种情况下，引入的2'-氟模拟了天然的2'-羟基，这表明氟原子可以接受氢键。在每种情况下，天然羟基都与嘌呤环外胺相互作用。我们的结果深入了解了有机氟的性质，并为RNA中2'-羟基与环外氨基之间的三级相互作用提出了一种可能的通用生化特征。
