5-HETEROARYL-2'-DEOXYURIDINE ANALOGS - SYNTHESIS AND INCORPORATION INTO HIGH-AFFINITY OLIGONUCLEOTIDES

被引：102

作者：

GUTIERREZ, AJ ^{[1
]}

TERHORST, TJ ^{[1
]}

MATTEUCCI, MD ^{[1
]}

FROEHLER, BC ^{[1
]}

机构：

[1] GILEAD SCI INC,FOSTER CITY,CA 94404

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 13期

关键词：

D O I：

10.1021/ja00092a003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of C-5 heteroaryl-2'-deoxyuridines were synthesized from 5-iodo-2'-deoxyuridine. Palladium catalyzed coupling with heteroarylstannanes proved to be a convenient and general method of preparation. Oligonucleotides containing pyridine-, thiophene-, thiazole-, and imidazole-substituted 2'-deoxyuridine analogs gave enhanced thermal stability to complementary RNA relative to thymidine. Thermal denaturation studies showed that oligodeoxynucleotides (ODNs) containing 5-(thiazol-2-yl)-2'-deoxyuridine exhibit the highest thermal denaturation (Tm) and therefore may increase the potency of these ODNs to inhibit gene expression in a sequence specific manner.

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页码：5540 / 5544

页数：5

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