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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 10: 4059 - 4065

DOI: https://doi.org/10.6023/cjoc202103058

ARTICLES

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

  • Fengmin Guo ,
  • Marko Trajkovski ,
  • Qiang Li ,
  • Janez Plavec ,
  • Zhen Xi ,
  • Chuanzheng Zhou
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  • 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
* Corresponding author. E-mail:

Received date: 2021-03-29

  Revised date: 2021-05-08

  Online published: 2021-06-17

Supported by

National Natural Science Foundation of China(21877064); National Natural Science Foundation of China(91953115); Natural Science Foundation of Tianjin City(20JCZDJC00830)

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Abstract

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

Cite this article

Fengmin Guo , Marko Trajkovski , Qiang Li , Janez Plavec , Zhen Xi , Chuanzheng Zhou . Synthesis and Structure of 4'-CF3-Uridine Modified Oligoribonucleotides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 4059 -4065 . DOI: 10.6023/cjoc202103058

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