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Development of Synthetic Methods for N-Labeled Nucleosides to Elucidate the Structural Recognition Ability of Nucleic Acids

开发N标记核苷的合成方法以阐明核酸的结构识别能力

基本信息

批准号：
06672104
负责人：
MAGOICHI Sako
金额：
$ 1.34万
依托单位：
Gifu Pharmaceutical University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1994
资助国家：
日本
起止时间：
1994 至 1995
项目状态：
已结题

项目摘要

NMR studies employing oligonucleotides regio-selectively labeled with ^<15>N atom provide valuable information regarding nucleic acid structures, nucleic acids binding with drugs, and nucleotide-protein interactions. The potential utility of the ^<15>N-labeled oligonucleotides has led to the considerable interest in the development of synthetic routes to the required ^<15>N-labeled nucleosides. The N_1-and N^6-positions of the adenine ring or N_3-and N^4-positions of the cytosine ring are good candidates for the ^<15>N-labeling, because they can form bydrogen bonds with suitable donors or acceptors in the nucleic acids, drugs, and proteins. On this line, we have developed a newly devised method for the debenzylation of N^6-benzyladenosine and N^4-benzylcytidine which involves oxidation with ammonium peroxydisulfate under mild conditions. The present method is based on the chemical reactivities of cation radical species of the nucleosides and provides simple and high-yield procedures for the [1-and 6-^<15>N] -labeled adenosines or [3-and 4-^<15>N] -labeled cytidines from inosines or uridines without protection of hydroxyl groups in the sugar moiety.

利用N原子区域选择性标记的寡核苷酸的NMR研究<15>提供了关于核酸结构、核酸与药物的结合以及核苷酸-蛋白质相互作用的有价值的信息。N<15>-标记的寡核苷酸的潜在效用已经导致对开发所需的N-标记的核苷的合成路线的相当大的兴趣<15>。腺嘌呤环的N_1-和N_6-位或胞嘧啶环的N_3-和N_4-位是很好的标记候选者<15>，因为它们可以与核酸、药物和蛋白质中合适的供体或受体形成氢键。在这条路线上，我们开发了一种新设计的N^6-苄基腺苷和N^4-苄基胞苷的脱苄基化方法，该方法包括在温和条件下用过硫酸铵进行氧化。本发明的方法基于核苷的阳离子自由基种类的化学反应性，并且提供了用于从肌苷或尿苷制备[1-和6-^<15>N] -标记的腺苷或[3-和4-^<15>N] -标记的胞苷的简单且高产率的方法，而无需保护糖部分中的羟基。