Počet záznamů: 1

Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate

  1. 1.
    SYSNO ASEP0360664
    Druh ASEPJ - Článek v odborném periodiku
    Zařazení RIVJ - Článek v odborném periodiku
    NázevSynthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate
    Tvůrce(i)Kóšiová, Ivana (UOCHB-X) - Buděšínský, Miloš (UOCHB-X) - Panova, Natalya (UOCHB-X) - Rosenberg, Ivan (UOCHB-X)
    Celkový počet autorů4
    Rozsah stran2856 - 2860
    Zdroj.dok.Organic & Biomolecular Chemistry - ISSN 1477-0520
    Poč.str.5 s.
    Jazyk dok.eng - angličtina
    Země vyd.GB - Velká Británie
    Klíč. slovaphosphonate internucleotide linkage ; organosulfur compounds ; NTP analogues ; nucleosides ; nucleotides
    Vědní obor RIVCC - Organická chemie
    CEPKAN200520801 GA AV ČR - Akademie věd
    GA202/09/0193 GA ČR - Grantová agentura ČR
    GA203/09/0820 GA ČR - Grantová agentura ČR
    LC06061 GA MŠk - Ministerstvo školství, mládeže a tělovýchovy
    CEZAV0Z40550506 - UOCHB-X (2005-2011)
    UTISI000288904500037
    DOI10.1039/c0ob00738b
    AnotaceSynthesis of novel nucleotide analogues 5'-deoxynucleoside-5'-S-methylphosphonates, starting from 5'-deoxy-5'-haloribonucleosides, 5'-O-tosylribonucleosides, and 2'-O-triflylnucleosides, is described. The phosphonothiolation of these compounds was achieved using S-(diisopropylphosphonomethyl) isothiouronium tosylate, a new, odourless, and efficient equivalent of mercaptomethylphosphonate. The thiolate anion of mercaptomethylphosphonate was generated in situ from the isothiouronium salt in both protic and aprotic solvents using two equivalents of sodium iso-propoxide. The prepared nucleoside 5'-S-methylphosphonates were deprotected, and the free phosphonic acids transformed into diphosphoryl derivatives (the NTP analogues). Both mononucleotides and NTP analogues were studied as substrates/inhibitors of several enzymes that are involved in the nucleoside/nucleotide metabolism.
    PracovištěÚstav organické chemie a biochemie
    KontaktJana Procházková, janap@uochb.cas.cz, Tel.: 220 183 418 ; Michaela Záluská, zaluska@uochb.cas.cz, Tel.: 232 002 579
    Rok sběru2012