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异鸟苷掺入的富鸟嘌呤寡核苷酸的合成
引用本文:王延龄,潘鹤龄,杨振军,张亮仁,张礼和. 异鸟苷掺入的富鸟嘌呤寡核苷酸的合成[J]. 中国药物化学杂志, 2004, 14(4): 225-228
作者姓名:王延龄  潘鹤龄  杨振军  张亮仁  张礼和
作者单位:北京大学药学院天然药物及仿生药物国家重点实验室,北京,100083
基金项目:国家自然科学基金,教育部重点实验室基金
摘    要:
目的改进异鸟苷单体的合成路线,合成异鸟苷掺入的富鸟嘌呤的寡核苷酸.方法以6-O-苄基鸟嘌呤为原料,经环氧开环、催化氢化、水解还原制备异鸟苷,经多步反应后得到异鸟苷亚磷酰化产物,采用固相合成方法合成异鸟苷掺入的富含鸟嘌呤的寡核苷酸.结果与结论经环氧开环能够区域选择性地得到N9取代的单一产物,收率提高到40%,并成功地合成了异鸟苷掺入的富含嘌呤十六聚寡核苷酸.本合成路线具有区域选择性强、路线简单、易操作、收率高等优点.

关 键 词:药物化学  制备  化学合成  寡核苷酸  异鸟苷  区域选择性
文章编号:1005-0108(2004)04-0225-04
修稿时间:2004-03-06

Synthesis of iso-guanosine incorporated G-rich oligonucleotide
WANG Yan-ling,PAN He-ling,YANG Zhen-jun,ZHANG Liang-ren,ZHANG Li-he. Synthesis of iso-guanosine incorporated G-rich oligonucleotide[J]. Chinese Journal of Medicinal Chemistry, 2004, 14(4): 225-228
Authors:WANG Yan-ling  PAN He-ling  YANG Zhen-jun  ZHANG Liang-ren  ZHANG Li-he
Abstract:
Aim To improve the synthesis of isoguanosine monomer and to synthesize isoguanosine incorporated G-rich oligonucleotide.Methods Starting from 6- O -benzylguanine which reacted with epoxide 1,then was hydrolyzed and reduced,the isoguanosine was achieved.The phosphoroimidated isoguanosine was then given via several steps and solid-phase synthesis strategy was used for the synthesis of G-rich oligonucleotide.Results N9 subsititued isoguanosine was obtained regioselectively by the ring open reaction,and the yield was improved to 40%.The isoguanosine incorporated 16-mer G-rich oligonucleotide was successfully synthesized.
Keywords:medicinal chemistry  preparation  chemical synthesis  oligonucleotide  isoguanosine  regioselectivity
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