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Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

SYSNO ASEP	0360650
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Tetrofuranose nucleoside phosphonic acids: Synthesis and properties
Author(s)	Poláková, Ivana (UOCHB-X) Buděšínský, Miloš (UOCHB-X)_{RID, ORCID} Točík, Zdeněk (UOCHB-X) Rosenberg, Ivan (UOCHB-X)_{RID, ORCID}
Number of authors	4
Source Title	Collection of Czechoslovak Chemical Communications. - : Ústav organické chemie a biochemie AV ČR, v. v. i. - ISSN 0010-0765 Roč. 76, č. 5 (2011), s. 503-536
Number of pages	34 s.
Language	eng - English
Country	CZ - Czech Republic
Keywords	tetrofuranosyl phosphonate ; nucleotide analogues ; phosphonomethoxy nucleosides ; sugar hydroxyphosphonates
Subject RIV	CC - Organic Chemistry
R&D Projects	KAN200520801 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
	GA203/09/0820 GA ČR - Czech Science Foundation (CSF)
	LC06061 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
	LC06077 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000290280100011
DOI	10.1135/cccc2011038
Annotation	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).
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2012

Number of the records: 1