Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

0360650 - ÚOCHB 2012 RIV CZ eng J - Journal Article
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
R&D Projects: GA AV ČR KAN200520801; GA ČR GA203/09/0820; GA MŠMT(CZ) LC06061; GA MŠMT(CZ) LC06077
Institutional research plan: CEZ:AV0Z40550506
Keywords : tetrofuranosyl phosphonate * nucleotide analogues * phosphonomethoxy nucleosides * sugar hydroxyphosphonates
Subject RIV: CC - Organic Chemistry
Impact factor: 1.283, year: 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).
Permanent Link: http://hdl.handle.net/11104/0198150