Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 28, Pages 10207-10219Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500582
Keywords
chain structures; DNA structures; nitrogen heterocycles; nucleosides; silver
Categories
Funding
- ChemBiotech, Munster, Germany
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Reverse Watson-Crick DNA with parallel-strand orientation (ps DNA) has been constructed. Pyrrolo-dC (PyrdC) nucleosides with phenyl and pyridinyl residues linked to the 6position of the pyrrolo[2,3-d]pyrimidine base have been incorporated in 12- and 25-mer oligonucleotide duplexes and utilized as silver-ion binding sites. Thermal-stability studies on the parallel DNA strands demonstrated extremely strong silver-ion binding and strongly enhanced duplex stability. Stoichiometric UV and fluorescence titration experiments verified that a single (2py)PyrdC-(2py)PyrdC pair captures two silver ions in ps DNA. A structure for the PyrdC silver-ion base pair that aligns 7-deazapurine bases head-to-tail instead of head-to-head, as suggested for canonical DNA, is proposed. The silver DNA double helix represents the first example of a ps DNA structure built up of bidentate and tridentate reverse Watson-Crick base pairs stabilized by a dinuclear silver-mediated PyrdC pair.
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