Journal
DALTON TRANSACTIONS
Volume 42, Issue 45, Pages 16080-16089Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3dt51691a
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- NRW Graduate School of Chemistry
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The artificial nucleobases 6-(2'-thienyl)-purine (6TP) and 6-(2'-furyl)-purine (6FP) have been investigated in terms of their applicability in metal-mediated base pairs. In principle, these nucleobases should be capable of providing an S, N- and O,N-coordination environment, respectively. Two metal complexes have been synthesized and structurally characterized, using the N9-methylated derivatives of 6TP and 6FP as model nucleobases. The silver(I) complex [Ag(9-Me6TP)(CH3CN)(NO3)](n) is of polymeric nature. The thienyl substituent is not involved in metal binding. In contrast, the dinuclear copper(II) complex [Cu(9-Me6FP)Cl-2(OH2)](2) clearly shows that the furyl substituent can participate in the coordination of the metal ion. Oligonucleotide double helices comprising a 6TP: 6TP or a 6FP: 6FP mispair are slightly stabilized in the presence of silver(I). However, a distinction between the formation of a metal-mediated base pair and an unspecific binding event cannot be finally made. Based on these studies, it is proposed that the formation of Hoogsteen-type metal-mediated base pairs should be the more promising alternative compared with the originally anticipated Watson-Crick-type metal-mediated base pairs.
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