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

Title
A new DNA building block, 4′-selenothymidine: Synthesis and modification to 4′-seleno-AZT as a potential anti-HIV agent
Authors
Alexander V.Choi W.J.Chun J.Kim H.O.Jeon J.H.Tosh D.K.Lee H.W.Chandra G.Choi J.Jeong L.S.
Ewha Authors
정낙신최원준
Issue Date
2010
Journal Title
Organic Letters
ISSN
1523-7060JCR Link
Citation
vol. 12, no. 10, pp. 2242 - 2245
Indexed
SCI; SCIE; SCOPUS WOS scopus
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. © 2010 American Chemical Society.
DOI
10.1021/ol1005906
Appears in Collections:
약학대학 > 약학과 > Journal papers
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