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{"title":"核苷的亚砜- click反应和双重标记","authors":"Guillaume Clavé, Jean-Jacques Vasseur, Michael Smietana","doi":"10.1002/cpnc.120","DOIUrl":null,"url":null,"abstract":"<p>This article contains detailed synthetic procedures for the implementation of the sulfo-click reaction to nucleoside derivatives. First, 3′-<i>O</i>-TBDMS-protected nucleosides are converted to their corresponding 4′-thioacid derivatives in three steps. Then, various conjugates are synthetized via a biocompatible and chemoselective coupling procedure using sulfonyl azide partners. Finally, to illustrate the potential of the sulfo-click reaction, a nucleoside bearing two orthogonal azido groups is synthesized and engaged in one-pot dual labeling through a sulfo-click/copper-catalyzed azide-alkyne cycloaddition (CuAAC) cascade. The high efficiency of the sulfo-click reaction as applied to nucleosides opens up new possibilities in the context of bioconjugation. © 2020 Wiley Periodicals LLC.</p><p><b>Basic Protocol 1</b>: General protocol for the synthesis of 4′-thioacid-nucleoside derivatives</p><p><b>Basic Protocol 2</b>: Implementation of the sulfo-click reaction</p><p><b>Basic Protocol 3</b>: Synthesis of 3′-azido-4′-(carboxamido)ethane-sulfonyl azide-3′-deoxythymidine</p><p><b>Basic Protocol 4</b>: Detailed synthetic procedure for one-pot double-click conjugations</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2020-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.120","citationCount":"0","resultStr":"{\"title\":\"The Sulfo-Click Reaction and Dual Labeling of Nucleosides\",\"authors\":\"Guillaume Clavé, Jean-Jacques Vasseur, Michael Smietana\",\"doi\":\"10.1002/cpnc.120\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>This article contains detailed synthetic procedures for the implementation of the sulfo-click reaction to nucleoside derivatives. First, 3′-<i>O</i>-TBDMS-protected nucleosides are converted to their corresponding 4′-thioacid derivatives in three steps. Then, various conjugates are synthetized via a biocompatible and chemoselective coupling procedure using sulfonyl azide partners. Finally, to illustrate the potential of the sulfo-click reaction, a nucleoside bearing two orthogonal azido groups is synthesized and engaged in one-pot dual labeling through a sulfo-click/copper-catalyzed azide-alkyne cycloaddition (CuAAC) cascade. The high efficiency of the sulfo-click reaction as applied to nucleosides opens up new possibilities in the context of bioconjugation. © 2020 Wiley Periodicals LLC.</p><p><b>Basic Protocol 1</b>: General protocol for the synthesis of 4′-thioacid-nucleoside derivatives</p><p><b>Basic Protocol 2</b>: Implementation of the sulfo-click reaction</p><p><b>Basic Protocol 3</b>: Synthesis of 3′-azido-4′-(carboxamido)ethane-sulfonyl azide-3′-deoxythymidine</p><p><b>Basic Protocol 4</b>: Detailed synthetic procedure for one-pot double-click conjugations</p>\",\"PeriodicalId\":10966,\"journal\":{\"name\":\"Current Protocols in Nucleic Acid Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2020-11-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/cpnc.120\",\"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.120\",\"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.120","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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