1. Silver(I)-mediated base pairing involving an S-glycosidic GNA nucleoside analogue.
- Author
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Schönrath, Isabell, Aukam, Hanne, Jasper-Peter, Beate, and Müller, Jens
- Subjects
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BASE pairs , *DNA synthesis , *SOLID-phase synthesis , *SILVER sulfide , *OLIGONUCLEOTIDE synthesis , *SILVER ions , *SILVER , *DEOXYCYTIDINE - 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]
- Published
- 2022
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