简易合成天然修饰核苷2'-脱氧古鸟苷  

The Facile Synthesis of Natural Modified Nucleoside 2'-Deoxyarchaeosine

作　　者：匡爽 彭静 田佳 吴明智 明新 KUANG Shuang;PENG Jing;TIAN Jia;WU Mingzhi;MING Xin(School of Pharmacy,Chengdu Medical College,Chengdu Sichuan 610500,China)

机构地区：[1]成都医学院药学院,四川成都610500

出　　处：《江西师范大学学报（自然科学版）》2022年第3期234-239,共6页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：教育部留学回国人员科研启动基金资助项目.

摘　　要：该文用改良的Pinner反应(通过加乙酰氯到甲醇中产生HCl,取代直接通HCl气体),将7-氰基-7-脱氮-2'-脱氧鸟苷(dPreQ _(0))转化为7-甲脒基-7-脱氮-2'-脱氧鸟苷(2'-脱氧古鸟苷,dG^(+)),产率为92.59%,其化学结构经核磁共振、高分辨质谱分析确证.优化了关键中间体dPreQ_(0)的合成纯化工艺.采用改良的Pinner反应,以2-氨基-4-氯吡咯并[2,3-d]嘧啶为起始物,通过7步反应制备dG^(+)的总反应产率达到33%.dG^(+)及其中间体的合成方法对其规模化合成具有重要意义,也为生物技术的发展提供支持.The chemical synthesis of naturally occurring 2'-deoxyarchaeosine(dG^(+))is achieved from dPreQ_(0) by improved Pinner reaction(adding acetyl chloride to methanol in an ice bath,instead of blowing hydrogen chloride gas),with yield of 92.59%.The structure of dG^(+)is confirmed by NMR and HR-MS.The protocol of key intermedium-7-cyano-2'-deoxy-7-deazaguanosine(dPreQ_(0))is optimized.The total yield of dG^(+)is 33%through 7 steps,using 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine as starting material.The synthetic process of dG^(+)and its intermediums is of great importance for their scale-up synthesis,which will provide beneficial significance for the development of biotechnology.

关 键 词：2'-脱氧古鸟苷(dG^(+)) 7-氰基-7-脱氮-2'-脱氧鸟苷(dPreQ_(0)) 天然修饰DNA 化学合成 

分 类 号：R914.4[医药卫生—药物化学]