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Silver(I)-mediated base pairing involving an S-glycosidic GNA nucleoside analogue.
- Source :
-
Nucleosides, Nucleotides & Nucleic Acids . 2022, Vol. 41 Issue 1, p23-35. 13p. - Publication Year :
- 2022
-
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 [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15257770
- Volume :
- 41
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Nucleosides, Nucleotides & Nucleic Acids
- Publication Type :
- Academic Journal
- Accession number :
- 154269133
- Full Text :
- https://doi.org/10.1080/15257770.2021.1994146