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Imidazolo‐dC Metal‐Mediated Base Pairs: Purine Nucleosides Capture Two Ag + Ions and Form a Duplex with the Stability of a Covalent DNA Cross‐Link
Author(s) -
Mei Hui,
Ingale Sachin A.,
Seela Frank
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404422
Subject(s) - duplex (building) , dna , covalent bond , base pair , chemistry , purine , nucleic acid , metal , ion , nucleobase , metal ions in aqueous solution , stereochemistry , crystallography , biochemistry , enzyme , organic chemistry
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.