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Silver(I)-mediated base pairing involving an S-glycosidic GNA nucleoside analogue
- Source :
- Nucleosides, Nucleotides & Nucleic Acids. 41:23-35
- Publication Year :
- 2021
- Publisher :
- Informa UK Limited, 2021.
-
Abstract
- The 4S-Ag(I)-C base pair (4S, 3-((2-(methylthio)pyrimidin-4-yl)thio)propane-1,2-diol; C, deoxycytidine) represents the first metal-mediated base pair comprising an S-glycosidic nucleoside analogue. We report here the synthesis of the phosphoramidite suitable for the automated solid-phase synthesis of DNA oligonucleotides containing 4S and its silver(I)-binding ability. The DNA duplexes comprising a 4S:C mispair exhibit a large thermal stabilization upon the addition of one equivalent of silver ions, giving rise to the formation of the above-mentioned silver(I)-mediated base pair. By formally replacing the sulfur atom in the glycosidic bond by an oxygen atom, i.e., by applying 3-((2-(methylthio)pyrimidin-4-yl)oxy)propane-1,2-diol (4 O) as the artificial nucleoside analogue, the participation of this atom as a donor atom in silver(I)-mediated base pairing is shown to be neglectable.Supplemental data for this article is available online at.
Details
- ISSN :
- 15322335 and 15257770
- Volume :
- 41
- Database :
- OpenAIRE
- Journal :
- Nucleosides, Nucleotides & Nucleic Acids
- Accession number :
- edsair.doi...........98d5b8524c0c4ce343315e4559cc1cc6