Počet záznamů: 1

Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

  1. 1.
    0360650 - UOCHB-X 2012 RIV CZ eng J - Článek v odborném periodiku
    Poláková, Ivana - Buděšínský, Miloš - Točík, Zdeněk - Rosenberg, Ivan
    Tetrofuranose nucleoside phosphonic acids: Synthesis and properties.
    Collection of Czechoslovak Chemical Communications. Roč. 76, č. 5 (2011), s. 503-536 ISSN 0010-0765
    Grant CEP: GA AV ČR KAN200520801; GA ČR GA203/09/0820; GA MŠk(CZ) LC06061; GA MŠk(CZ) LC06077
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: tetrofuranosyl phosphonate * nucleotide analogues * phosphonomethoxy nucleosides * sugar hydroxyphosphonates
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 1.283, rok: 2011

    New isoelectronic, non-isosteric phosphonate analogues of nucleoside 5'-phosphates featuring the phosphorus moiety directly attached on the sugar ring in the C4' position are described. The analogues were synthesised by a nucleosidation reaction from tetrofuranosyl phosphonate synthons and silylated nucleobases. The pyrimidine compounds with erythro and threo configuration in both D- and L-series were prepared, and the structures were assigned by NMR spectroscopy. NMR conformational studies show that all calculated conformers have a maximum pucker in the range typical for nucleosides. In all compounds, the S-type conformer is preferred. One of the prepared phosphonic acids was found to be a competitive inhibitor of thymidine phosphorylase (Ki = 4 .mu.M).
    Trvalý link: http://hdl.handle.net/11104/0198150