Highly Regioselective Methylation of Guanosine Nucleotides: An Efficient Synthesis of 7-Methylguanosine Nucleotides

Q4 Chemistry

Current Protocols in Nucleic Acid Chemistry Pub Date : 2019-10-09 DOI:10.1002/cpnc.100

Annamalai Senthilvelan, Muthian Shanmugasundaram, Anilkumar R. Kore

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Abstract

This article describes a simple, reliable, efficient, and general method for the synthesis of 7-methylguanosine nucleotides such as 7-methylguanosine 5′-O-monophosphate (m⁷GMP), 7-methylguanosine 5′-O-diphosphate (m⁷GDP), 7-methyl-2′-deoxyguanosine 5′-O-triphosphate (m⁷2′dGTP), and 7-methylguanosine 5′-O-triphosphate (m⁷GTP) starting from the corresponding guanosine nucleotide is described. The present protocol involves methylation reaction of guanosine nucleotide using dimethyl sulfate as a methylating agent and water as a solvent at room temperature to provide the corresponding 7-methylguanosine nucleotide in good yields with high purity (>99.5%). It is noteworthy that the present methylation reaction proceeds smoothly under aqueous conditions that is highly regioselective to afford exclusive 7-methylguanosine nucleotide. © 2019 by John Wiley & Sons, Inc.

Basic Protocol: Synthesis of 7-methylguanosine nucleotides.

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鸟苷核苷酸的高度区域选择性甲基化:7‐甲基鸟苷核苷酸的高效合成

本文描述了一种简单、可靠、高效、通用的方法，从相应的鸟苷核苷酸开始，合成7‐甲基鸟苷5′‐O‐单磷酸(m7GMP)、7‐甲基鸟苷5′‐O‐二磷酸(m7GDP)、7‐甲基鸟苷2′‐O‐三磷酸(m72′dgtp)和7‐甲基鸟苷5′‐O‐三磷酸(m7GTP)。目前的方案是在室温下，以硫酸二甲酯为甲基化剂，水为溶剂，进行鸟苷核苷酸的甲基化反应，得到相应的7‐甲基鸟苷核苷酸，产率高，纯度高(>99.5%)。值得注意的是，目前的甲基化反应在具有高度区域选择性的水条件下顺利进行，从而产生排他的7‐甲基鸟苷核苷酸。©2019 by John Wiley & Sons, Inc。

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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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