Journal
JOURNAL OF INORGANIC BIOCHEMISTRY
Volume 191, Issue -, Pages 85-93Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.jinorgbio.2018.10.013
Keywords
DNA; Imidazole; Metal-mediated base pair; Silver; Copper
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The use of imidazole-4-carboxylate (X) as an artificial nucleobase in metal-mediated base pairing is reported. Towards this end, the corresponding deoxyribonucleoside was synthesized and structurally characterized as its sodium salt (sodium 1,2-dideoxy-1-(4-carboxyimidazol-1-yl)-D-ribofuranose). The deoxyribonucleoside was incorporated into different DNA duplexes (parallel-stranded and antiparallel-stranded), and their Cu(II)- and Ag(I)binding behavior was investigated. It was shown that both X-Cu(II)-X and X-Ag(I)-X base pairs can be formed, with the former being more stabilizing than the latter. The formation of an X-Cu(II)-X base pair is accompanied by an increase in the duplex melting temperature of approximately 20 degrees C for antiparallel-stranded duplexes and of 12 degrees C for the parallel-stranded duplex under investigation. Imidazole-4-carboxylate represents the first imidazole-based nucleoside for Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X-Cu(II)-X and X-Ag(I)-X base pairs are proposed, too, based on molecular structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate.
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