Jump to main content
Jump to site search

Issue 45, 2013
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Jun 2013, accepted on 31 Jul 2013 and first published on 01 Aug 2013


Article type: Paper
DOI: 10.1039/C3DT51691A
Citation: Dalton Trans., 2013,42, 16080-16089
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements