Silver(I)-mediated base pairing involving an S-glycosidic GNA nucleoside analogue.

Isabell Schönrath, Hanne Aukam, Beate Jasper-Peter, Jens Müller

Nucleosides, nucleotides & nucleic acids 2022

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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.

Citation

Isabell Schönrath, Hanne Aukam, Beate Jasper-Peter, Jens Müller. Silver(I)-mediated base pairing involving an S-glycosidic GNA nucleoside analogue. Nucleosides, nucleotides & nucleic acids. 2022;41(1):23-35