4'-三氟甲基尿苷修饰的寡核苷酸合成及修饰位点构象研究  

Synthesis and Structure of 4'-CF_(3)-Uridine Modified Oligoribonucleotides

作　　者：郭丰敏 Marko Trajkovski 李强[1] Janez Plavec 席真[1] 周传政[1] Guo Fengmin;Trajkovski Marko;Li Qiang;Plavec Janez;Xi Zhen;Zhou Chuanzheng(State Key Laboratory of Elemento-organic Chemistry and Department of Chemical Biology,College of Chemistry,Nankai University,Tianjin 300071;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)

机构地区：[1]南开大学化学学院元素有机化学国家重点实验室,天津300071 [2]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

出　　处：《有机化学》2021年第10期4059-4065,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21877064,91953115);天津市自然科学基金(No.20JCZDJC00830)资助项目.

摘　　要：合成了4'-CF3修饰的尿苷亚磷酰胺单体,并通过固相合成将其引入了寡聚核苷酸链.分子动态模拟和NMR的结构研究,以及寡聚核苷酸的基本生化性质测定都表明4'-CF3修饰将该核苷酸的核糖锁定在不常见的South构象.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.

关 键 词：核酸 RNA结构 氟化学 

分 类 号：O621.3[理学—有机化学]