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.
authors.affiliation: Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Varughese
authors.initials: V
authors.lastname: Alexander
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Jeongha
authors.initials: J
authors.lastname: Chun
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Ji Hye
authors.initials: JH
authors.lastname: Jeon
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Tosh
authors.forename: Hyuk Woo
authors.initials: HW
authors.lastname: Lee
authors.forename: Girish
authors.initials: G
authors.lastname: Chandra
authors.forename: Jungwon
authors.initials: J
authors.lastname: Choi
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry / Q000187:drug effects*; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C551384:4'-seleno-AZT; C531225:4'-selenothymidine; D019380:Anti-HIV Agents; D016566:Organoselenium Compounds; D015215:Zidovudine; D004247:DNA; D013936:Thymidine