A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent

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

doi:10.1021/ol1005906

A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent

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

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2242-2245
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	10
DOIs	https://doi.org/10.1021/ol1005906
State	Published - 21 May 2010

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title = "A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent",

abstract = "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.",

author = "Varughese Alexander and Choi, {Won Jun} and Jeongha Chun and Kim, {Hea Ok} and Jeon, {Ji Hye} and Tosh, {Dilip K.} and Lee, {Hyuk Woo} and Girish Chandra and Jungwon Choi and Jeong, {Lak Shin}",

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AU - Chun, Jeongha

AU - Kim, Hea Ok

AU - Jeon, Ji Hye

AU - Tosh, Dilip K.

AU - Lee, Hyuk Woo

AU - Chandra, Girish

AU - Choi, Jungwon

AU - Jeong, Lak Shin

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A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent

Abstract

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