Stereospecific syntheses of 3′-deuterated pyrimidine nucleosides and their site-specific incorporation into DNA

被引：13

作者：

Chirakul, P ^{[1
]}

Sigurdsson, ST ^{[1
]}

机构：

[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol034102g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2'-Deoxy-3'-deutero pyrimidines have been synthesized in high yields and incorporated into deoxyoligonucleotides using standard phosphoramidite chemistry. A key synthetic step is a stereospecific reduction of 3'-keto nucleosides using sodium triacetoxyborodeuteride to give 3'-deuterated thymidine and 2'-deoxy uridine nucleosides. Conversion of the corresponding phorphoramidites 7a and 7b to 4-triazolo derivatives has, for the first time, enabled incorporation of 2'-deoxy-3'-deutero cytidine and 2'-deoxy-3'-deutero-5-methyl cytidine into oligonucleotides.

引用

页码：917 / 919

页数：3

共 16 条

[11] Nucleic acid related compounds .94. Remarkably high stereoselective reductions of 2'- and 3'-ketonucleoside derivatives to give arabino, ribo, and xylofuranosyl nucleosides with hydrogen isotopes at C2' and C3' [J].