Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4059-4065.DOI: 10.6023/cjoc202103058 Previous Articles     Next Articles



郭丰敏a, Marko Trajkovskib, 李强a, Janez Plavecb, 席真a, 周传政a,*()   

  1. a 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
    b 斯洛文尼亚国家化学研究所核磁中心 卢布尔雅那大学化学和化工学院 卢布尔雅那 1000 斯洛文尼亚
  • 收稿日期:2021-03-29 修回日期:2021-05-08 发布日期:2021-06-17
  • 通讯作者: 周传政
  • 基金资助:
    国家自然科学基金(21877064); 国家自然科学基金(91953115); 天津市自然科学基金(20JCZDJC00830)

Synthesis and Structure of 4'-CF3-Uridine Modified Oligoribonucleotides

Fengmin Guoa, Marko Trajkovskib, Qiang Lia, Janez Plavecb, Zhen Xia, Chuanzheng Zhoua()   

  1. a State Key Laboratory of Elemento-organic Chemistry and Department of Chemical Biology, College of Chemistry, Nankai University, Tianjin 300071
    b Slovenian NMR Centre, National Institute of Chemistry, University of Ljubljana, Faculty of Chemistry and Chemical Technology, Ljubljana, EN-FIST Centre of Excellence, Hajdrihova 19, Ljubljana 1000, Slovenia
  • Received:2021-03-29 Revised:2021-05-08 Published:2021-06-17
  • Contact: Chuanzheng Zhou
  • Supported by:
    National Natural Science Foundation of China(21877064); National Natural Science Foundation of China(91953115); Natural Science Foundation of Tianjin City(20JCZDJC00830)

The synthesis and structure of 4'-CF3-uridine modified ribonucleotides are reported. Active 4'-CF3-uridine (4'-TfMU) phosphoramidite was prepared and successfully incorporated into oligonucleotides based on solid-supported synthesis. Molecular dynamics simulations and NMR studies of the 4'-TfMU modified oligonucleotides revealed that the ribose of 4'-TfMU was constrained in the South conformation, which was corroborated by the biochemical properties of the 4'-TfMU modified oligonucleotide, such as their affinity to complementary strands and transesterification kinetics. The South-constrained conformation, together with the intense 19F NMR signal of the 4'-TfMU makes it an ideal probe for studying the structure and function of RNA.

Key words: nucleic acids, RNA structures, fluorine chemistry