Cu^II-mediated DNA base pairing of a triazole-4-carboxylate nucleoside prepared by click chemistry

Abstract

Artificial metal-mediated DNA base pairing is a promising strategy for creating highly functionalized DNA supramolecules. Here we report a novel ligand-type triazole-4-carboxylate (TazC) nucleoside that is readily prepared by the...

Metal-dependent base pairing of bifacial iminodiacetic acid-modified uracil bases for switching DNA hybridization partner

“…The T m of duplex 1 · 2 is lower than that of duplex 1T · 2T containing a T–T mismatch pair (37.4 °C). This is thought to be due to the electrostatic repulsion between the dcaU bases with negatively charged carboxylates, similar to the 5-carboxyuracil 38 and 4-carboxyimidazole 32,50–52 nucleobases reported previously.…”

6-Pyrazolylpurine and its deaza derivatives as nucleobases for silver(I)-mediated base pairing with pyrimidines

“…Towards this end, numerous artificial nucleobases have been developed [ 3 , 4 ]. While the canonical nucleobases thymine and cytosine are known to form homoleptic metal-mediated base pairs with mercury(II) and silver(I) [ 5 ], the development of artificial metal-coordinating nucleobases allows the incorporation of other metal ions, too [ 6 – 10 ]. Likewise, the introduction of more than one metal ion per base pair can be achieved [ 11 , 12 ].…”

Metal-dependent activity control of a compact-sized 8–17 DNAzyme based on metal-mediated unnatural base pairing

“…[12][13][14][15][16][17] Although many metal-dependent DNAzymes have been identified by in vitro selection processes, chemical modification of existing DNAzymes is expected to be a more powerful method to confer metal-responsiveness on DNAzymes at will. To this end, unnatural metal-mediated base pairs, [18][19][20][21][22][23] formed by metal complexation between two ligand-bearing nucleotides and a bridging metal ion, have been exploited as metal-responsive units in DNA. A series of RNA-cleaving DNAzymes, such as E5, 24 NaA43, 25 and Ag10c, 26 have been reshaped into metaldependent allosteric DNAzymes by incorporating metalmediated artificial base pairs such as H-Cu II -H, [12][13][14] Im C -Cu II -Im C , 15 eA-Cu II -eA, 16 and U OH -Gd III -U OH .…”