Synthesis of 6-(2-thienyl)purine nucleoside derivatives that form unnatural base pairs with pyridin-2-one nucleosides

被引：41

作者：

Fujiwara, T

Kimoto, M

Sugiyama, H

Hirao, I

Yokoyama, S

机构：

[1] RIKEN, JST, ERATO, Yokoyama CytoLog Project, Wako, Saitama 3510198, Japan

[2] Univ Tokyo, Grad Sch Sci, Dept Biophys & Biochem, Bunkyo Ku, Tokyo 1130033, Japan

[3] RIKEN, Cellular Signaling Lab, Wako, Saitama 3510198, Japan

[4] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Div Biofunct Mol, Chiyoda Ku, Tokyo 1010062, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 16期

关键词：

D O I：

10.1016/S0960-894X(01)00415-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Unnatural bases. 2-amino-6-(2-thienyl)purine and 2-amino-6-(2-furanyl)purine, were newly designed to replace the previously developed purine analogue, 2-amino-6-(N,N-dimethylamino)purine. which specifically pairs with pyridin-2-one. These nucleoside derivatives were synthesized via the 6-substitution of 6-iodopurine nucleosides with tributylstannylthiophene or tributylstannylfuran. As compared with 2-amino-6-(N,:V-dimethylamino)purine, 2-amino-6-(2-thienyl)purine reduced the interference in the stacking interactions with the neighboring bases in a DNA duplex and improved the efficiency of the enzymatic incorporation of the nucleoside triphosphate of pyridin-2-one opposite the unnatural base. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2221 / 2223

页数：3

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