三环及多环核苷的设计、合成及在荧光标记中的应用

项目名称： 三环及多环核苷的设计、合成及在荧光标记中的应用

项目编号： No.21272059

项目类型： 面上项目

立项/批准年度： 2013

项目学科： 数理科学和化学

项目作者： 郭海明

作者单位： 河南师范大学

项目金额： 80万元

中文摘要： 三环及多环嘌呤核苷通常具有良好的荧光和生物活性，它们可以通过扩大碱基的共轭体系，大大增加化合物的荧光强度。该类化合物通常可以用来测定核酸序列，检测病原体，分析基因的表达，在诊断遗传疾病的发病机理方面发挥着巨大的作用。因此对该类化合物的合成及荧光性质进行研究具有重要的理论意义和应用价值。到目前为止，该类化合物的报道较少、化合物的多样性不足、合成步骤长、收率低，因此设计合成结构新颖、灵敏度高的多环嘌呤核苷衍生物就成为一个不可忽视的课题。本课题组近年来一直从事核苷（酸）类似物的结构修饰，合成了400多种新核苷类化合物，具有丰富的经验积累。本项目拟以6氯及2氯嘌呤核苷（脱氧核苷）为原料，首先在6位或2位引入芳胺或烯胺基团，然后通过C-H活化\分子内胺化反应合成结构多样的具有三环或多环嘌呤核苷类化合物，进一步合成多环核苷标记的寡聚核苷酸，并对所合成的化合物的应用进行研究。

中文关键词： 三环核苷；多环核苷；荧光标记；合成；嘌呤

英文摘要： Tricyclic and polycyclic purine nucleosides usually have good fluorescence and biological activities. They have greatly increased the fluorescence intensity via expanding the conjugated system of purine base. They have been used to determine the nucleic acid sequence, detect pathogens and analyze the gene expression so as to play a huge role in the diagnosis of pathogenesis of the genetic diseases. Therefore, the synthesis of these compounds and the study of their fluorescence properties have important theoretical significance and application value. So far, this field have some faults, such as, less report, inadequacy diversity, long process, multi steps and low yields. It is a very important task to synthesize the fluorescence purine nucleoside derivatives which own novel structure and high sensitivity. In recent years, we have been working on modification of nucleosides/nucleotides. We have synthesized more than 400 kinds of novel nucleoside analogues and accumulated valuable experiences. Using 6-Cl/2-Cl-purine nucleoside(deoxyribonucleoside) as material, we plan to introduce the arylamine or enamine group into 6-/2-of pruine, then synthesize tricyclic or polycyclic purine nucleoside compounds with structural diversity via C-H amination reaction, further derive oligomeric nucleoside compounds labeled by polycy

英文关键词： tricyclic nucleoside；polycyclic nucleoside；fluorescence labeling；synthesis；purine