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{"title":"Synthesis of Azobenzene Derivative Phosphoramidites for Incorporation into Oligonucleotides.","authors":"Matthew L Hammill, Jean-Paul Desaulniers","doi":"10.1002/cpnc.107","DOIUrl":null,"url":null,"abstract":"<p><p>This article contains the detailed synthesis and characterization protocols of azobenzene containing siRNAs, which have photoswitchable properties effectively controlled with light. First, the azobenzene scaffolds are synthesized via reduction of nitrophenyl alcohols in the presence of zinc. Next, the hydroxyl group of azobenzene derivatives are protected with a dimethoxytrityl (DMT) group, followed by phosphitylation with 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite. These phosphoramidite monomers are compatible with automated solid-phase oligonucleotide synthesis to generate azobenzene-containing oligonucleotides. © 2020 by John Wiley & Sons, Inc. Basic Protocol 1: Synthesis of 4,4'-bis(hydroxymethyl)-azobenzene phosphoramidite Basic Protocol 2: Synthesis of 4,4'-bis(hydroxyethyl)-azobenzene phosphoramidite Basic Protocol 3: Synthesis, purification and characterization of oligonucleotides containing azobenzene derivatives.</p>","PeriodicalId":10966,"journal":{"name":"Current Protocols in Nucleic Acid Chemistry","volume":"81 1","pages":"e107"},"PeriodicalIF":0.0000,"publicationDate":"2020-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/cpnc.107","citationCount":"4","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Protocols in Nucleic Acid Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/cpnc.107","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 the detailed synthesis and characterization protocols of azobenzene containing siRNAs, which have photoswitchable properties effectively controlled with light. First, the azobenzene scaffolds are synthesized via reduction of nitrophenyl alcohols in the presence of zinc. Next, the hydroxyl group of azobenzene derivatives are protected with a dimethoxytrityl (DMT) group, followed by phosphitylation with 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite. These phosphoramidite monomers are compatible with automated solid-phase oligonucleotide synthesis to generate azobenzene-containing oligonucleotides. © 2020 by John Wiley & Sons, Inc. Basic Protocol 1: Synthesis of 4,4'-bis(hydroxymethyl)-azobenzene phosphoramidite Basic Protocol 2: Synthesis of 4,4'-bis(hydroxyethyl)-azobenzene phosphoramidite Basic Protocol 3: Synthesis, purification and characterization of oligonucleotides containing azobenzene derivatives.
偶氮苯类磷酰胺的合成及其与寡核苷酸的结合。
本文详细介绍了含偶氮苯的sirna的合成和表征方法,这些sirna具有有效的光开关特性。首先,在锌的存在下,通过还原硝基苯醇合成偶氮苯支架。其次,偶氮苯衍生物的羟基被二甲氧基三甲基(DMT)保护,然后与2-氰乙基- n, n -二异丙基氯磷酰胺酰化。这些磷酸酰胺单体兼容于自动固相寡核苷酸合成,以生成含偶氮苯的寡核苷酸。©2020 by John Wiley & Sons, Inc。基本程序1:合成4,4'-双(羟甲基)-偶氮苯磷酰胺基本程序2:合成4,4'-双(羟乙基)-偶氮苯磷酰胺基本程序3:合成、纯化和表征含偶氮苯衍生物的寡核苷酸。
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