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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-HIV Agents / chemical synthesis
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / pharmacology*
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Cell Line
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Crystallography, X-Ray
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DNA / chemistry
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DNA / drug effects*
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HIV-1 / drug effects*
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Humans
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Microbial Sensitivity Tests
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Models, Molecular
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Molecular Conformation
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Organoselenium Compounds / chemical synthesis
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Organoselenium Compounds / chemistry
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Organoselenium Compounds / pharmacology*
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Thymidine / analogs & derivatives*
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Thymidine / chemical synthesis
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Thymidine / chemistry
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Thymidine / pharmacology
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Zidovudine / analogs & derivatives*
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Zidovudine / chemical synthesis
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Zidovudine / chemistry
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Zidovudine / pharmacology
Substances
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4'-seleno-AZT
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4'-selenothymidine
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Anti-HIV Agents
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Organoselenium Compounds
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Zidovudine
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DNA
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Thymidine