Synthesis of 5′-Thio-3′-O-ribonucleoside Phosphoramidites

被引:3
|
作者
Li, Nan-Sheng [1 ]
Lu, Jun
Piccirilli, Joseph A. [1 ]
机构
[1] Univ Chicago, Dept Biochem & Mol Biol, 929 East 57th St, Chicago, IL 60637 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期
关键词
SOLID-PHASE SYNTHESIS; RIBOZYME-MEDIATED CLEAVAGE; GENERAL ACID CATALYSIS; HAMMERHEAD RIBOZYME; BRIDGING; 5-PHOSPHOROTHIOATE; DNA TOPOISOMERASE; SUBSTRATE-ANALOG; BASE CATALYSIS; RNA; MECHANISM;
D O I
10.1021/acs.joc.7b01484
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemical synthesis of phosphoramidite derivatives of all four 5'-deoxy-5'-thioribonucleosides is described. These phosphoramidites contained trityl (A, G, C, and U), dimethoxytrityl (A and G), or tert-butyldisulfanyl (G) as the 5'-S-protecting group. The application of several of these phosphoramidites for solid-phase synthesis of oligoribonucleotides containing a 2'-O-photocaged 5'-S-phosphorothiolate linkage or 5'-thiol-labeled RNAs is also further investigated.
引用
收藏
页码:12003 / 12013
页数:11
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