Issue 45, 2013

6-Substituted purines containing thienyl or furyl substituents as artificial nucleobases for metal-mediated base pairing

Abstract

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)Cl2(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.

Graphical abstract: 6-Substituted purines containing thienyl or furyl substituents as artificial nucleobases for metal-mediated base pairing

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2013
Accepted
31 Jul 2013
First published
01 Aug 2013

Dalton Trans., 2013,42, 16080-16089

6-Substituted purines containing thienyl or furyl substituents as artificial nucleobases for metal-mediated base pairing

I. Sinha, J. Kösters, A. Hepp and J. Müller, Dalton Trans., 2013, 42, 16080 DOI: 10.1039/C3DT51691A

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