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TETROFURANOSE NUCLEOSIDE PHOSPHONIC ACIDS: SYNTHESIS AND PROPERTIES.
- Source :
- Collection of Czechoslovak Chemical Communications; 2011, Vol. 76 Issue 5, p503-536, 34p, 13 Diagrams, 1 Chart, 1 Graph
- Publication Year :
- 2011
-
Abstract
- 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. The results of 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 and is more significant in α-D-threo-compounds. Studies on inhibition of thymidine phosphorylase revealed that one of the prepared phosphonic acids was a competitive inhibitor of the enzyme (K<subscript>i</subscript> = 4 μM). [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00100765
- Volume :
- 76
- Issue :
- 5
- Database :
- Complementary Index
- Journal :
- Collection of Czechoslovak Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 60447302
- Full Text :
- https://doi.org/10.1135/cccc2011038