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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10.1021/ol1005906

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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\}",

year = "2010",

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doi = "10.1021/ol1005906",

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AU - Alexander, Varughese

AU - Choi, Won Jun

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

PY - 2010/5/21

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AB - 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.

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JF - Organic Letters

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ER -

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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