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{"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}
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Abstract
This article contains detailed synthetic procedures for the implementation of the sulfo-click reaction to nucleoside derivatives. First, 3′-O -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.
Basic Protocol 1 : General protocol for the synthesis of 4′-thioacid-nucleoside derivatives
Basic Protocol 2 : Implementation of the sulfo-click reaction
Basic Protocol 3 : Synthesis of 3′-azido-4′-(carboxamido)ethane-sulfonyl azide-3′-deoxythymidine
Basic Protocol 4 : Detailed synthetic procedure for one-pot double-click conjugations
核苷的亚砜- click反应和双重标记
本文详细介绍了实现核苷衍生物的亚砜-咔嗒反应的合成过程。首先,通过三步将3 ' - o - tbdms保护的核苷转化为相应的4 ' -硫代酸衍生物。然后,通过生物相容性和化学选择性偶联过程,利用磺酰叠氮化物偶联物合成了各种偶联物。最后,为了说明亚砜-咔嗒反应的潜力,合成了一个带有两个正交叠氮基团的核苷,并通过亚砜-咔嗒/铜催化叠氮-炔环加成(CuAAC)级联进行了一锅双标记。应用于核苷的磺胺-咔嗒反应的高效率为生物偶联开辟了新的可能性。©2020 Wiley期刊有限责任公司。基本方案1:合成4 ' -硫代酸-核苷衍生物的一般方案基本方案2:磺胺反应的实施基本方案3:合成3 ' -叠氮-4 ' -(羧胺)乙烷-磺酰叠氮-3 ' -脱氧胸苷基本方案4:一锅双偶联的详细合成程序
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