Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage

0364307 - ÚOCHB 2012 RIV US eng J - Článek v odborném periodiku
Králíková, Šárka - Buděšínský, Miloš - Barvík, I. - Masojídková, Milena - Točík, Zdeněk - Rosenberg, Ivan
Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage.
Nucleosides Nucleotides & Nucleic Acids. Roč. 30, 7/9 (2011), s. 524-543. ISSN 1525-7770. E-ISSN 1532-2335
Grant CEP: GA ČR GA202/09/0193; GA AV ČR KAN200520801; GA MŠMT(CZ) LC06061
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: alpha-hydroxy-phosphonate linkage * ApA analogues * phosphonate internucleotide bond * NMR conformational study
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 0.899, rok: 2011

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.
Trvalý link: http://hdl.handle.net/11104/0199826