Synthesis of DNA and RNA Oligonucleotides Containing a Dual-Purpose Selenium-Modified Fluorescent Nucleoside Probe.

Q4 Chemistry
Ashok Nuthanakanti, Seergazhi G Srivatsan
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引用次数: 0

Abstract

Development of efficient tools that would enable direct correlation of nucleic acid structure and recognition in solution and in solid state at atomic resolution is highly desired. In this context, we recently developed dual‐purpose nucleoside probes made of a 5‐selenophene‐modified uracil core, which serves both as a conformation‐sensitive fluorophore and as an X‐ray crystallography phasing agent. In this article, we provide a detailed synthetic procedure to synthesize the phosphoramidites of 5‐selenophene‐modified 2′‐deoxyuridine and 5‐selenophene‐modified uridine analogs. We also describe their site‐specific incorporation into therapeutically relevant DNA and RNA oligonucleotide motifs by an automated solid support synthesis protocol. The dual‐purpose and minimally invasive nature of the probes enables efficient analysis of the conformation and ligand binding abilities of bacterial decoding site RNA (A‐site) and G‐quadruplex structures of the human telomeric overhang in real time by fluorescence and in 3D by X‐ray crystallography. © 2020 by John Wiley & Sons, Inc.
含有双用途硒修饰荧光核苷探针的DNA和RNA寡核苷酸的合成。
开发一种高效的工具,能够在溶液和固体状态下以原子分辨率直接关联核酸结构和识别,是非常需要的。在这种情况下,我们最近开发了由5-硒烯修饰的尿嘧啶核心制成的双用途核苷探针,它既可以作为构象敏感的荧光团,也可以作为x射线晶体学分相剂。本文详细介绍了5-硒代苯酚修饰的2'-脱氧尿嘧啶和5-硒代苯酚修饰的尿嘧啶类似物的磷酰胺的合成方法。我们还描述了它们的位点特异性结合到治疗相关的DNA和RNA寡核苷酸基序通过自动化固体支持合成协议。该探针具有双重用途和微创性,能够通过荧光实时分析细菌解码位点RNA (a位点)和人类端粒悬垂的g四重结构的构象和配体结合能力,并通过x射线晶体学进行三维分析。©2020 by John Wiley & Sons, Inc。基本方案1:合成5-硒烯-2'-脱氧尿苷2及其磷酰胺5支持方案1:合成2-(三正丁基锡基)硒烯2支持方案2:合成5'- o- dmt保护的5-碘-2'-脱氧尿苷3基本方案2:合成5-硒烯-修饰的尿苷7及其磷酰胺11基本方案3:合成含有5-硒烯-修饰的2'-脱氧尿苷2的DNA寡核苷酸基本方案4:含5-硒烯修饰尿苷的RNA寡核苷酸的合成
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来源期刊
Current Protocols in Nucleic Acid Chemistry
Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry
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期刊介绍: Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.
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