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{"title":"三氟甲基化嘌呤核糖核苷和核糖核苷酸的高效合成","authors":"Mikolaj Chrominski, Joanna Kowalska, Jacek Jemielity","doi":"10.1002/cpnc.118","DOIUrl":null,"url":null,"abstract":"<p>The protocols presented in this article describe highly detailed synthesis of trifluoromethylated purine nucleotides and nucleosides (G and A). The procedure involves trifluoromethylation of properly protected (acetylated) nucleosides, followed by deprotection leading to key CF<sub>3</sub>-containing nucleosides. This gives synthetic access to 8-CF<sub>3</sub>-substituted guanosine derivatives and three adenosine derivatives (8-CF<sub>3</sub>, 2-CF<sub>3</sub>, and 2,8-diCF<sub>3</sub>). In further steps, phosphorylation and phosphate elongation (for selected examples) result in respective trifluoromethylated nucleoside mono-, di-, and triphosphates. Support protocols are included for compound handling, purification procedures, analytical sample preparation, and analytical techniques used throughout the performance of the basic protocols. © 2020 Wiley Periodicals LLC.</p><p><b>Basic Protocol 1</b>: Synthesis of trifluoromethylated guanosine and adenosine derivatives</p><p><b>Basic Protocol 2</b>: Synthesis of trifluoromethylated guanosine and adenosine monophosphates</p><p><b>Basic Protocol 3</b>: Synthesis of phosphorimidazolides of <sup>8-CF3</sup>GMP and <sup>8-CF3</sup>AMP</p><p><b>Basic Protocol 4</b>: Synthesis of trifluoromethylated guanosine and adenosine oligophosphates</p><p><b>Support Protocol 1</b>: TLC sample preparation and analysis</p><p><b>Support Protocol 2</b>: Purification protocol for Basic Protocol 1</p><p><b>Support Protocol 3</b>: HPLC analysis and preparative HPLC</p><p><b>Support Protocol 4</b>: Ion-exchange chromatography</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":"83 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2020-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.118","citationCount":"1","resultStr":"{\"title\":\"Efficient Synthesis of Trifluoromethylated Purine Ribonucleosides and Ribonucleotides\",\"authors\":\"Mikolaj Chrominski, Joanna Kowalska, Jacek Jemielity\",\"doi\":\"10.1002/cpnc.118\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The protocols presented in this article describe highly detailed synthesis of trifluoromethylated purine nucleotides and nucleosides (G and A). The procedure involves trifluoromethylation of properly protected (acetylated) nucleosides, followed by deprotection leading to key CF<sub>3</sub>-containing nucleosides. This gives synthetic access to 8-CF<sub>3</sub>-substituted guanosine derivatives and three adenosine derivatives (8-CF<sub>3</sub>, 2-CF<sub>3</sub>, and 2,8-diCF<sub>3</sub>). In further steps, phosphorylation and phosphate elongation (for selected examples) result in respective trifluoromethylated nucleoside mono-, di-, and triphosphates. Support protocols are included for compound handling, purification procedures, analytical sample preparation, and analytical techniques used throughout the performance of the basic protocols. © 2020 Wiley Periodicals LLC.</p><p><b>Basic Protocol 1</b>: Synthesis of trifluoromethylated guanosine and adenosine derivatives</p><p><b>Basic Protocol 2</b>: Synthesis of trifluoromethylated guanosine and adenosine monophosphates</p><p><b>Basic Protocol 3</b>: Synthesis of phosphorimidazolides of <sup>8-CF3</sup>GMP and <sup>8-CF3</sup>AMP</p><p><b>Basic Protocol 4</b>: Synthesis of trifluoromethylated guanosine and adenosine oligophosphates</p><p><b>Support Protocol 1</b>: TLC sample preparation and analysis</p><p><b>Support Protocol 2</b>: Purification protocol for Basic Protocol 1</p><p><b>Support Protocol 3</b>: HPLC analysis and preparative HPLC</p><p><b>Support Protocol 4</b>: Ion-exchange chromatography</p>\",\"PeriodicalId\":10966,\"journal\":{\"name\":\"Current Protocols in Nucleic Acid Chemistry\",\"volume\":\"83 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2020-09-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/cpnc.118\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current Protocols in Nucleic Acid Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cpnc.118\",\"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.118","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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Efficient Synthesis of Trifluoromethylated Purine Ribonucleosides and Ribonucleotides
The protocols presented in this article describe highly detailed synthesis of trifluoromethylated purine nucleotides and nucleosides (G and A). The procedure involves trifluoromethylation of properly protected (acetylated) nucleosides, followed by deprotection leading to key CF3 -containing nucleosides. This gives synthetic access to 8-CF3 -substituted guanosine derivatives and three adenosine derivatives (8-CF3 , 2-CF3 , and 2,8-diCF3 ). In further steps, phosphorylation and phosphate elongation (for selected examples) result in respective trifluoromethylated nucleoside mono-, di-, and triphosphates. Support protocols are included for compound handling, purification procedures, analytical sample preparation, and analytical techniques used throughout the performance of the basic protocols. © 2020 Wiley Periodicals LLC.
Basic Protocol 1 : Synthesis of trifluoromethylated guanosine and adenosine derivatives
Basic Protocol 2 : Synthesis of trifluoromethylated guanosine and adenosine monophosphates
Basic Protocol 3 : Synthesis of phosphorimidazolides of 8-CF3 GMP and 8-CF3 AMP
Basic Protocol 4 : Synthesis of trifluoromethylated guanosine and adenosine oligophosphates
Support Protocol 1 : TLC sample preparation and analysis
Support Protocol 2 : Purification protocol for Basic Protocol 1
Support Protocol 3 : HPLC analysis and preparative HPLC
Support Protocol 4 : Ion-exchange chromatography