An Efficient Gram-Scale Chemical Synthesis of Purine Locked Nucleic Acid Nucleoside-5'-O-Triphosphates

Muthian Shanmugasundaram; Annamalai Senthilvelan; Anilkumar R. Kore

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An Efficient Gram-Scale Chemical Synthesis of Purine Locked Nucleic Acid Nucleoside-5'-O-Triphosphates

机译：An Efficient Gram-Scale Chemical Synthesis of Purine Locked Nucleic Acid Nucleoside-5'-O-Triphosphates

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This article presents a simple, reliable, straight-forward, general, and efficient chemical method for the gram-scale synthesis of purine locked nucleic acid (LNA) nucleotides, such as LNA guanosine-5'-O-triphosphate (LNA-GTP) and LNA adenosine-5'-O-triphosphate (LNA-ATP), starting from the corresponding nucleoside. The reaction pathway employs an improved protection-free "one-pot, three-step" Ludwig synthetic strategy. The first step involves monophosphorylation of nucleoside with phosphorus oxychloride followed by reaction with tributylammonium pyrophosphate and subsequent hydrolysis of the resulting cyclic intermediate to furnish the corresponding LNA nucleotide in good yields. It is noteworthy that the reaction affords high-purity (>99.5) LNA nucleotide after diethylaminoethyl Sepharose column purification.

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来源
《Current Protocols in Nucleic Acid Chemistry》 |2022年第6期|e436-1-e436-9|共9页
作者
Muthian Shanmugasundaram; Annamalai Senthilvelan; Anilkumar R. Kore;
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作者单位

Life Sciences Solutions Group, Thermo Fisher Scientific, Austin, Texas;

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原文格式 PDF
正文语种英语
中图分类生物化学;
关键词
chemical synthesis; DNA; locked nucleic acid; oligonucleotides; one-pot synthesis; RNA;

An Efficient Gram-Scale Chemical Synthesis of Purine Locked Nucleic Acid Nucleoside-5'-O-Triphosphates

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