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

Song Mao; Hsu-Chun Tsai; Jia Sheng

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

机译：合成5-Cyanomethyluridine (cnm5U)和5-Cyanouridine cn5U Phosphoramidites及其纳入RNA寡核苷酸

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This article contains detailed synthetic protocols for preparation of 5-cyanomethyluridine (cnm~5U) and 5-cyanouridine (cn5U) phosphoramidites. The synthesis of the cnm5U phosphoramidite building block starts with commercially available 5-methyluridine (m~5C), followed by bromination of the 5-methyl group to install the cyano moiety using TMSCN/TBAF. The cn5U phosphoramidite is obtained by regular Vorbruggen glycosylation of the protected ribofuranose with silylated 5-cyanouracil. These two modifiedphospho-ramidites 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.

机译：本文包含详细的合成协议准备5-cyanomethyluridine (cnm ~ 5 u)和5-cyanouridine phosphoramidites (cn5U)。合成的cnm5U phosphoramidite建筑块始于商用5-methyluridine (m ~ 5 c),其次是溴化5-methyl集团安装含氰基的一部分使用TMSCN / TBAF。通过定期Vorbruggen糖基化受保护的ribofuranose甲烷硅基化的5-cyanouracil。modifiedphospho-ramidites适合在固相合成的RNA寡核苷酸使用常规amidite化学。协议提供两个新颖的建筑块构造RNA-based疗法。

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《Current Protocols in Nucleic Acid Chemistry》 |2020年第1期|e114/1-e114/17|共17页
作者
Song Mao; Hsu-Chun Tsai; Jia Sheng;
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作者单位

Department of Chemistry and The RNA Institute, University at AlbanyState University of New York, Albany, New York;

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正文语种英语
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关键词
Bromination; Nucleic acids; Building blocksOligonucleotidesSolid phasesIncorporationSolid-Phase Synthesismethyl groupphosphoramiditesynthesis;

机译：溴化;核酸;建筑phasesIncorporationSolid-Phase Synthesismethylgroupphosphoramiditesynthesis;

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

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