新型 DNA 构建模块 4′-硒代胸苷：合成及修饰为 4′-硒代 AZT 作为一种潜在的抗 HIV 药物。
A new DNA building block, 4'-selenothymidine: synthesis and modification to 4'-seleno-AZT as a potential anti-HIV agent.
机构信息
Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
出版信息
Org Lett. 2010 May 21;12(10):2242-5. doi: 10.1021/ol1005906.
The first synthesis of 4'-selenothymidine (1), a novel DNA building block, and 4'-seleno-AZT (2) was accomplished from 2-deoxy-d-ribose via stereoselective formation of 2-deoxy-4-seleno-d-furanose 17 and a Pummerer-type base condensation as key steps. 4'-Selenothymidine (1) was discovered to adopt the same 2'-endo/3'-exo conformation as thymidine, which is unusual in that 4'-selenouridine has the opposite conformation to that of uridine.
4'-硒代胸苷（1），一种新型的 DNA 构建模块，以及 4'-硒代 AZT（2）的首次合成是从 2-脱氧-D-核糖出发，通过立体选择性形成 2-脱氧-4-硒代-D-呋喃糖 17 和 Pummerer 型碱基缩合作为关键步骤完成的。发现 4'-硒代胸苷（1）采用与胸苷相同的 2'-内/3'-外构象，这是不寻常的，因为 4'-硒代尿苷的构象与尿苷相反。
Zotero 插件