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The Synthesis and Properties of Oligodeoxyribonucleotides with Single Mono- and Diphosphoryldithio Internucleotide Links |
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| Authors: | Metelev V. G. Kubareva E. A. Romanova E. A. Oretskaya T. S. |
| Affiliation: | (1) Chemical Faculty, Moscow State University, Vorob'evy gory, GSP-3, Moscow, 119899, Russia;(2) Belozersky Institute of Physicochemical Biology, Moscow State University, Vorob'evy gory, GSP-3, Moscow, 119992, Russia |
| Abstract: | The synthesis of oligodeoxyribonucleotides bearing mono- and diphosphoryldisulfide internucleotide links was optimized. Oligonucleotide 3"-phosphorothioates were modified using the thiophosphoryl–disulfide exchange with preactivated 5"-deoxy-5"-mercaptooligonucleotides or 5"-phosphorothioate derivatives both with and without a complementary template. The lack of template was shown to differently affect the product ratio (homo- and heterodimers) in the reactions of mono- and diphosphoryldisulfide-containing oligonucleotides. A replacement of one natural phosphodiester bond in 15–16-mer duplexes by a mono- or diphosphoryldisulfide group causes a slight thermal destabilization of the corresponding duplex. The disulfide recombination of the resulting compounds was studied. |
| Keywords: | modified oligonucleotides oligonucleotide 3" -phosphorothioates phosphoryldisulfide links thiol– disulfide exchange |
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