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

Organic & Biomolecular Chemistry
Dana HockováIvan Rosenberg

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.

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Citations

Jul 25, 2009·Current Opinion in Chemical Biology·Oyindasola Oyelaran, Jeffrey C Gildersleeve
Feb 11, 2021·Beilstein Journal of Organic Chemistry·Kārlis-Ēriks KriķisMāris Turks

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