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5‐Mercuricytosine: An Organometallic Janus Nucleobase
Author(s) -
Ukale Dattatraya,
Shinde Vaishali S.,
Lönnberg Tuomas
Publication year - 2016
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.201600851
Subject(s) - oligonucleotide , nucleobase , chemistry , duplex (building) , deprotonation , thymine , base pair , guanine , crystallography , monomer , dna , stereochemistry , nucleotide , polymer , organic chemistry , biochemistry , ion , gene
The base‐pairing properties of 5‐mercuricytosine have been explored at the monomer level by NMR titrations and at the oligonucleotide level by melting temperature measurements. The NMR studies revealed a relatively high affinity for guanine, hypoxanthine, and uridine, that is, bases that are deprotonated upon coordination of Hg II . Within an oligonucleotide duplex, 5‐mercuricytosine formed Hg II ‐mediated base pairs with thymine and guanine. In the former case, the duplex formed was as stable as the respective duplex comprising solely Watson–Crick base pairs. Based on detailed thermodynamic analysis of the melting curves, the stabilization by the Hg II ‐mediated base pairs may be attributed to a comparatively low entropic penalty of hybridization.