可交联嘌呤类脱氧核苷类似物的合成  

Synthesis of Cross-linkable Purine Deoxynucleoside Analogs

作　　者：许永娣 马星光 孙亚伟[1] XU Yongdi;MA Xingguang;SUN Yawei(College of Chemistry and Chemical Engineering, China University of Petroleum(Huadong), Qingdao 266580, China)

机构地区：[1]中国石油大学(华东)化学化工学院,山东青岛266580

出　　处：《合成化学》2022年第4期299-304,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21573288)。

摘　　要：可交联嘌呤类脱氧核苷是天然脱氧核苷类似物,可与互补链中配对碱基上的胺基发生链间交联反应,导致DNA双链发生不可逆转的交联,对开发核苷类药物和控制修饰基因表达等方面有重要应用。本文开发了一条新的合成路径,该方法以商业化的1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-D-呋喃核糖为起始原料,经由简便的合成路线制备了目标产物。该方法以结晶的方式对目标产物进行了纯化,优化了合成工艺,为大规模生产该类化合物提供了新思路。Cross-linkable purine deoxynucleosides are natural deoxynucleoside analogs that can undergo inter-strand cross-linking reactions with the amino groups on the nucleobases in the nucleic acids,leading the irreversible cross-linking of DNA strand.These artificial deoxynucleosides plays important roles in developing nucleoside drugs and the control of modified gene expression.In this paper,we have developed a new synthetic route by applying the commercial 1-chloro-2-deoxy-3,5-di-O-toluoyl-D-ribofuranose as the starting material.The synthesis process was optimized and the desired products were purified by crystallization,which provides us a new synthetic method for large-scale production of these compounds.

关 键 词：可交联核苷类似物 人工合成核苷 迈克尔加成 嘌呤 碱基 核糖 结晶 

分 类 号：O62[理学—有机化学]