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Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage

SYSNO ASEP	0364307
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage
Author(s)	Králíková, Šárka (UOCHB-X)_RID Buděšínský, Miloš (UOCHB-X)_{RID, ORCID} Barvík, I. (CZ) Masojídková, Milena (UOCHB-X) Točík, Zdeněk (UOCHB-X) Rosenberg, Ivan (UOCHB-X)_{RID, ORCID}
Number of authors	6
Source Title	Nucleosides Nucleotides & Nucleic Acids. - : Taylor & Francis - ISSN 1525-7770 Roč. 30, 7/9 (2011), s. 524-543
Number of pages	20 s.
Language	eng - English
Country	US - United States
Keywords	alpha-hydroxy-phosphonate linkage ; ApA analogues ; phosphonate internucleotide bond ; NMR conformational study
Subject RIV	CC - Organic Chemistry
R&D Projects	GA202/09/0193 GA ČR - Czech Science Foundation (CSF)
	KAN200520801 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
	LC06061 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000296072200007
DOI	10.1080/15257770.2011.581259
Annotation	A complete series of the 2'–5' and 3'–5' regioisomeric types of r(ApA) and 2'-d(ApA) analogues with the α-hydroxy-phosphonate C3' -O-P-CH(OH)-C4" internucleotide linkage, isopolar but non-isosteric with the phosphodiester one, were synthesized and their hybridization properties with polyU studied. Due to chirality on the 5'-carbon atom of the modified internucleotide linkage, each regioisomeric type of ApA dimer is split into epimeric pairs. The role of 5'-hydroxyl of the alpha-hydroxy-phosphonate moiety during hybridization was studied. NMR conformational study on modified sugar-phosphate backbone, along with hybridization measurements and MDS, revealed remarkable differences in the stability of complexes with polyU, depending on the 5'-carbon atom configuration.
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