Počet záznamů: 1

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

  1. 1.
    0360664 - UOCHB-X 2012 RIV GB eng J - Článek v odborném periodiku
    Kóšiová, Ivana - Buděšínský, Miloš - Panova, Natalya - Rosenberg, Ivan
    Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate.
    Organic & Biomolecular Chemistry. Roč. 9, č. 8 (2011), s. 2856-2860 ISSN 1477-0520
    Grant CEP: GA AV ČR KAN200520801; GA ČR GA202/09/0193; GA ČR GA203/09/0820; GA MŠk(CZ) LC06061
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: phosphonate internucleotide linkage * organosulfur compounds * NTP analogues * nucleosides * nucleotides
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 3.696, rok: 2011

    Synthesis 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.
    Trvalý link: http://hdl.handle.net/11104/0198164