[1]匡 爽,彭 静,田 佳,等.简易合成天然修饰核苷2'-脱氧古鸟苷[J].江西师范大学学报(自然科学版),2022,(03):234-239.[doi:10.16357/j.cnki.issn1000-5862.2022.03.03]
 KUANG Shuang,PENG Jing,TIAN Jia,et al.The Facile Synthesis of Natural Modified Nucleoside 2'-Deoxyarchaeosine[J].Journal of Jiangxi Normal University:Natural Science Edition,2022,(03):234-239.[doi:10.16357/j.cnki.issn1000-5862.2022.03.03]
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简易合成天然修饰核苷2'-脱氧古鸟苷()
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《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2022年03期
页码:
234-239
栏目:
化学
出版日期:
2022-05-25

文章信息/Info

Title:
The Facile Synthesis of Natural Modified Nucleoside 2'-Deoxyarchaeosine
文章编号:
1000-5862(2022)03-0234-06
作者:
匡 爽彭 静田 佳吴明智明 新*
成都医学院药学院,四川 成都 610500
Author(s):
KUANG ShuangPENG JingTIAN JiaWU MingzhiMING Xin*
School of Pharmacy,Chengdu Medical College,Chengdu Sichuan 610500,China
关键词:
+)' target="_blank" rel="external">2'-脱氧古鸟苷(dG+)0)' target="_blank" rel="external"> 7-氰基-7-脱氮-2'-脱氧鸟苷(dPreQ0) 天然修饰DNA 化学合成
Keywords:
+)' target="_blank" rel="external">2'-deoxyarchaeosine(dG+)0)' target="_blank" rel="external"> 7-cyano-2'-deoxy-7-deazaguanosine(dPreQ0) naturally modified DNA chemical synthesis
分类号:
R 914.4
DOI:
10.16357/j.cnki.issn1000-5862.2022.03.03
文献标志码:
A
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(dPreQ0)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dPreQ0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.
Abstract:
The chemical synthesis of naturally occurring 2'-deoxyarchaeosine(dG+)is achieved from dPreQ0 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(dPreQ0)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.

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备注/Memo

备注/Memo:
收稿日期:2021-03-05
基金项目:教育部留学回国人员科研启动基金资助项目.
通信作者:明 新(1972—),女,重庆万州人,副教授,博士,主要从事药物化学研究.E-mail:mingxin@cmc.edu.cn
更新日期/Last Update: 2022-05-25