Synthesis of 5‐Cyanomethyluridine (cnm 5 U) and 5‐Cyanouridine (cn 5 U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides
Synthesis of 5‐Cyanomethyluridine (cnm 5 U) and 5‐Cyanouridine (cn 5 U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides
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5-氰基甲基尿苷 (cnm 5 U) 和 5-氰基尿苷 (cn 5 U) 亚磷酰胺的合成及其掺入 RNA 寡核苷酸
DOI：
10.1002/cpnc.114
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发表时间：
2020
影响因子：
--
通讯作者：
Sheng, Jia
中科院分区：
文献类型：
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作者：
Mao, Song;Tsai, Hsu‐Chun;Sheng, Jia
本文详细介绍了5-氰基甲基尿苷（cnm 5 U）和5-氰基尿苷（cn 5 U）亚磷酰胺的合成方法。cnm 5 U亚磷酰胺结构单元的合成从市售的5-甲基尿苷（m5 C）开始，然后使用TMSCN/TBAF溴化5-甲基以安装氰基部分。cn 5 U亚磷酰胺通过用甲硅烷基化5-氰基尿嘧啶对受保护的呋喃核糖进行常规Vorbrüggen糖基化获得。这两种修饰的亚磷酰胺适合于使用常规的亚酰胺化学在固相上合成RNA寡核苷酸。我们的方案提供了两种用于构建基于RNA的疗法的新型构建模块。© 2020 Wiley Periodicals LLC.基本方案1：cnm 5 U和cn 5 U亚磷酰胺的制备基本方案2：cnm 5 U-和cn 5 U-修饰的RNA寡核苷酸的合成、纯化和表征
This article contains detailed synthetic protocols for preparation of 5‐cyanomethyluridine (cnm5U) and 5‐cyanouridine (cn5U) phosphoramidites. The synthesis of the cnm5U phosphoramidite building block starts with commercially available 5‐methyluridine (m5C), followed by bromination of the 5‐methyl group to install the cyano moiety using TMSCN/TBAF. The cn5U phosphoramidite is obtained by regular Vorbrüggen glycosylation of the protected ribofuranose with silylated 5‐cyanouracil. These two modified phosphoramidites are suitable for synthesis of RNA oligonucleotides on solid phase using conventional amidite chemistry. Our protocol provides access to two novel building blocks for constructing RNA‐based therapeutics. © 2020 Wiley Periodicals LLC.Basic Protocol 1: Preparation of cnm5U and cn5U phosphoramiditesBasic Protocol 2: Synthesis, purification, and characterization of cnm5U‐ and cn5U‐modified RNA oligonucleotides