A New DNA Building Block, 4′-Selenothymidine: Synthesis and Modification to 4′-Seleno-AZT as a Potential Anti-HIV Agent
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- 作者：Varughese Alexander ; Won Jun Choi ; Jeongha Chun ; Hea Ok Kim ; Ji Hye Jeon ; Dilip K. Tosh ; Hyuk Woo Lee ; Girish Chandra ; Jungwon Choi ; Lak Shin Jeong
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：May 21, 2010
- 年：2010
- 卷：12
- 期：10
- 页码：2242-2245
- 全文大小：202K
- 年卷期：v.12,no.10(May 21, 2010)
- ISSN：1523-7052
文摘
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.