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
DC Element | Wert | Sprache |
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dc.contributor.author | Yang, Haozhe | |
dc.contributor.author | Mei, Hui | |
dc.contributor.author | Seela, Frank | |
dc.date.accessioned | 2021-12-23T16:06:40Z | - |
dc.date.available | 2021-12-23T16:06:40Z | - |
dc.date.issued | 2015 | |
dc.identifier.issn | 09476539 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7501 | - |
dc.description.abstract | 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. | |
dc.description.sponsorship | ChemBiotech, Munster, Germany; We thank Mr. N.Q. Tran for the oligonucleotide synthesis and Dr. H. Letzel (Organisch-chemisches Institut, Universitat Munster, Germany) for measurement of the MALDI-TOF mass spectra. We also thank Dr. P. Leonard and Dr. S. Budow-Busse for their continuous support throughout the preparation of this manuscript. Financial support by ChemBiotech, Munster, Germany is highly appreciated. | |
dc.language.iso | en | |
dc.publisher | WILEY-V C H VERLAG GMBH | |
dc.relation.ispartof | CHEMISTRY-A EUROPEAN JOURNAL | |
dc.subject | chain structures | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | COMPLEXES | |
dc.subject | DNA structures | |
dc.subject | GUANINE | |
dc.subject | ISOCYTOSINE | |
dc.subject | ISOGUANINE-CYTOSINE | |
dc.subject | nitrogen heterocycles | |
dc.subject | NUCLEIC-ACID | |
dc.subject | nucleosides | |
dc.subject | OLIGONUCLEOTIDE DUPLEXES | |
dc.subject | PHENYLPYRROLOCYTOSINE | |
dc.subject | PYRIMIDINE BASE | |
dc.subject | silver | |
dc.subject | STRANDED DNA | |
dc.subject | TRIPLEX | |
dc.title | 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 | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/chem.201500582 | |
dc.identifier.isi | ISI:000357026700034 | |
dc.description.volume | 21 | |
dc.description.issue | 28 | |
dc.description.startpage | 10207 | |
dc.description.endpage | 10219 | |
dc.contributor.orcid | 0000-0001-7350-0688 | |
dc.contributor.researcherid | AAL-1705-2020 | |
dc.identifier.eissn | 15213765 | |
dc.publisher.place | POSTFACH 101161, 69451 WEINHEIM, GERMANY | |
dcterms.isPartOf.abbreviation | Chem.-Eur. J. |
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geprüft am 23.05.2024