Preparation of short oligonucleotides via the phosphoramidite method using a tetrazole promoter in a catalytic manner

被引:33
作者
Hayakawa, Y
Kataoka, M
机构
[1] Laboratory of Bioorganic Chemistry, Graduate School of Human Informatics, Nagoya University, Chikusa
关键词
D O I
10.1021/ja970685b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile phosphoramidite method using a tetrazole promoter in a catalytic manner has been developed for the condensation of a nucleoside 3'-phosphoramidite and a nucleoside, This method is particularly useful for a large-scale synthesis of short oligonucleotides, For example, dinucleoside phosphates are prepared on a multigram scale in 92-99% yields through the reaction of nucleoside 3'-N,N-diethylphosphoramidites (1.05 equiv) and 5'-O-free nucleosides (1.00 equiv) with 5-(p-nitrophenyl)-1H-tetrazole (NPT) (0.05 equiv) in the presence of molecular sieves 13X in acetonitrile (40 degrees C, 60 min) followed by trimethylsilyl triflate-catalyzed oxidation with bis(trimethylsilyl) peroxide in dichloromethane (40 degrees C, 10 min). The NPT-catalytic approach is also effective for the synthesis of longer deoxyribonucleotides such as d((5')CTACCTGT(3')) and 2'-5'- or 3'-5'-linked ribonucleotides.
引用
收藏
页码:11758 / 11762
页数:5
相关论文
共 29 条