Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides

Q4 Chemistry Current Protocols in Nucleic Acid Chemistry Pub Date : 2020-08-26 DOI:10.1002/cpnc.114

Song Mao, Hsu-Chun Tsai, Jia Sheng

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Abstract

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 phosphoramidites

Basic Protocol 2: Synthesis, purification, and characterization of cnm⁵U- and cn⁵U-modified RNA oligonucleotides

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5-氰甲基尿嘧啶(cnm5U)和5-氰脲嘧啶(cn5U)磷酰胺的合成及其与RNA寡核苷酸的结合

本文详细介绍了5-氰甲基尿嘧啶(cnm5U)和5-氰脲嘧啶(cn5U)磷酰胺的合成方法。cnm5U磷酰胺基块的合成始于市售的5-甲基尿嘧啶(m5C)，然后使用TMSCN/TBAF对5-甲基进行溴化以安装氰基部分。cn5U磷酰胺是由受保护的核呋喃糖与硅基化的5-氰脲嘧啶进行规则的vorbr糖基化得到的。这两种改性的磷酰胺适合于传统的酰胺化学在固相上合成RNA寡核苷酸。我们的方案为构建基于rna的疗法提供了两种新的构建模块。基本方案2:cnm5U-和cn5U修饰的RNA寡核苷酸的合成、纯化和表征

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Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry

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期刊介绍： Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.

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