Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 49, Pages 16248-16257Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404422
Keywords
DNA; nucleosides; silver
Categories
Funding
- ChemBiotech, Munster, Germany
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8-Phenylimidazolo-dC ((ph)ImidC, 2) forms metal-mediated DNA base pairs by entrapping two silver ions. To this end, the fluorescent purine 2-deoxyribonucleoside 2 has been synthesised and converted into the phosphoramidite 6. Owing to the ease of nucleobase deprotonation, the new Ag+-mediated base pair containing a purine skeleton is much stronger than that derived from the pyrrolo- [3,4-d]pyrimidine system ((ph)PyrdC, 1). The silver-mediated (ph)ImidC-(ph)ImidC base pair fits well into the DNA double helix and has the stability of a covalent cross-link. The formation of such artificial metal base pairs might not be limited to DNA but may be applicable to other nucleic acids such as RNA, PNA and GNA as well as other biopolymers.
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