title: Synthesis of conformationally locked carbocyclic nucleoside phosphonates to probe the active site of HIV-1 RT.
abstract: The conformationally locked carbocyclic nucleoside phosphonates 2 and 2' and key intermediates for the synthesis of 3 and 3' were prepared from a chiral cyclopentene derivative and epicholorohydrine, respectively. The structure of the nucleoside precursor 6 was confirmed by X-ray crystallography. These carbocyclic nucleoside phosphonates were designed to probe their binding interactions at the active site of HIV-1-RT.
authors.affiliation: Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, MD 21702, USA.
authors.forename: Hisao
authors.initials: H
authors.lastname: Saneyoshi
authors.forename: B Christie
authors.initials: BC
authors.lastname: Vu
authors.forename: Stephen H
authors.initials: SH
authors.lastname: Hughes
authors.forename: Paul L
authors.initials: PL
authors.lastname: Boyer
authors.forename: Stefan G
authors.initials: SG
authors.lastname: Sarafianos
authors.forename: Victor E
authors.initials: VE
authors.lastname: Marquez
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D020134:Catalytic Domain; D054303:HIV Reverse Transcriptase / Q000187:drug effects*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D063065:Organophosphonates; D018894:Reverse Transcriptase Inhibitors; C514824:reverse transcriptase, Human immunodeficiency virus 1; D054303:HIV Reverse Transcriptase; D000241:Adenosine
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