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Issue 15, 2015
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N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides

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Abstract

Protected N-branched nucleoside phosphonates containing adenine and thymine bases were prepared as the monomers for the introduction of aza-acyclic nucleotide units into modified oligonucleotides. The phosphotriester and phosphoramidite methods were used for the incorporation of modified and natural units, respectively. The solid phase synthesis of a series of nonamers containing one central modified unit was successfully performed in both 3′→5′ and 5′→3′ directions. Hybridization properties of the prepared oligoribonucleotides and oligodeoxyribonucleotides were evaluated. The measurement of thermal characteristics of the complexes of modified nonamers with the complementary strand revealed a considerable destabilizing effect of the introduced units. We also examined the substrate/inhibitory properties of aza-acyclic nucleoside phosphono-diphosphate derivatives (analogues of nucleoside triphosphates) but neither inhibition of human and bacterial DNA polymerases nor polymerase-mediated incorporation of these triphosphate analogues into short DNA was observed.

Graphical abstract: N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides

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Publication details

The article was received on 24 Oct 2014, accepted on 26 Feb 2015 and first published on 26 Feb 2015


Article type: Paper
DOI: 10.1039/C4OB02265C
Org. Biomol. Chem., 2015,13, 4449-4458

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    N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides

    D. Hocková, Š. Rosenbergová, P. Ménová, O. Páv, R. Pohl, P. Novák and I. Rosenberg, Org. Biomol. Chem., 2015, 13, 4449
    DOI: 10.1039/C4OB02265C

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