寡核苷酸合成后修饰构建C5位含羧酸等价物的嘧啶碱

Q4 Chemistry

Current Protocols in Nucleic Acid Chemistry Pub Date : 2019-07-03 DOI:10.1002/cpnc.91

Yuta Ito, Kazuki Yamamoto, Yoshiyuki Hari

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引用次数: 0

摘要

本单元描述了含有2′脱氧-5-三氟甲基尿苷和2′脱氧-5-三氟甲基胞苷的寡核苷酸（ONs）的合成后修饰。在ONs中，嘧啶碱C5位的三氟甲基使用碱性和胺溶液转化为各种羧酸当量。此外，用甲胺和氢氧化钠水溶液处理完全保护和控制孔玻璃（CPG）连接的ONs会导致所有保护基（4,4′-二甲氧基三苯甲基除外）的脱保护、CPG的裂解以及三氟甲基的同时转化，从而得到相应的含5取代嘧啶碱的ONs。©2019 John Wiley&Sons，股份有限公司版权所有。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Construction of Pyrimidine Bases Bearing Carboxylic Acid Equivalents at the C5 Position by Postsynthetic Modification of Oligonucleotides

This unit describes postsynthetic modification of oligonucleotides (ONs) containing 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine. In ONs, the trifluoromethyl group at the C5 position of pyrimidine bases is converted into a variety of carboxylic acid equivalents using alkaline and amine solutions. In addition, treating fully protected and controlled pore glass (CPG)-attached ONs with methylamine and sodium hydroxide aqueous solution results in deprotection of all protecting groups (except the 4,4′-dimethoxytrityl group), cleavage from CPG, and simultaneous conversion of the trifluoromethyl group to afford the corresponding ONs containing 5-substituted pyrimidine bases. © 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.