Pyrrolo-dC Metal-Mediated Base Pairs in the Reverse Watson-Crick Double Helix: Enhanced Stability of Parallel DNA and Impact of 6-Pyridinyl Residues on Fluorescence and Silver-Ion Binding

Autor(en): Yang, Haozhe
Mei, Hui
Seela, Frank
Stichwörter: chain structures; Chemistry; Chemistry, Multidisciplinary; COMPLEXES; DNA structures; GUANINE; ISOCYTOSINE; ISOGUANINE-CYTOSINE; nitrogen heterocycles; NUCLEIC-ACID; nucleosides; OLIGONUCLEOTIDE DUPLEXES; PHENYLPYRROLOCYTOSINE; PYRIMIDINE BASE; silver; STRANDED DNA; TRIPLEX
Erscheinungsdatum: 2015
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 21
Ausgabe: 28
Startseite: 10207
Seitenende: 10219
Zusammenfassung: 
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.
ISSN: 09476539
DOI: 10.1002/chem.201500582

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