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{"title":"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","authors":"Song Mao, Hsu-Chun Tsai, Jia Sheng","doi":"10.1002/cpnc.114","DOIUrl":null,"url":null,"abstract":"<p>This article contains detailed synthetic protocols for preparation of 5-cyanomethyluridine (cnm<sup>5</sup>U) and 5-cyanouridine (cn<sup>5</sup>U) phosphoramidites. The synthesis of the cnm<sup>5</sup>U phosphoramidite building block starts with commercially available 5-methyluridine (m<sup>5</sup>C), followed by bromination of the 5-methyl group to install the cyano moiety using TMSCN/TBAF. The cn<sup>5</sup>U 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.</p><p><b>Basic Protocol 1</b>: Preparation of cnm<sup>5</sup>U and cn<sup>5</sup>U phosphoramidites</p><p><b>Basic Protocol 2</b>: Synthesis, purification, and characterization of cnm<sup>5</sup>U- and cn<sup>5</sup>U-modified RNA oligonucleotides</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2020-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.114","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides\",\"authors\":\"Song Mao, Hsu-Chun Tsai, Jia Sheng\",\"doi\":\"10.1002/cpnc.114\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>This article contains detailed synthetic protocols for preparation of 5-cyanomethyluridine (cnm<sup>5</sup>U) and 5-cyanouridine (cn<sup>5</sup>U) phosphoramidites. The synthesis of the cnm<sup>5</sup>U phosphoramidite building block starts with commercially available 5-methyluridine (m<sup>5</sup>C), followed by bromination of the 5-methyl group to install the cyano moiety using TMSCN/TBAF. The cn<sup>5</sup>U 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.</p><p><b>Basic Protocol 1</b>: Preparation of cnm<sup>5</sup>U and cn<sup>5</sup>U phosphoramidites</p><p><b>Basic Protocol 2</b>: Synthesis, purification, and characterization of cnm<sup>5</sup>U- and cn<sup>5</sup>U-modified RNA oligonucleotides</p>\",\"PeriodicalId\":10966,\"journal\":{\"name\":\"Current Protocols in Nucleic Acid Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2020-08-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/cpnc.114\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current Protocols in Nucleic Acid Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.114\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.114","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"Chemistry","Score":null,"Total":0}
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