A1 Refereed original research article in a scientific journal
1,8-Dimercuri-6-Phenyl-1H-Carbazole as a Monofacial Dinuclear Organometallic Nucleobase
Authors: Dattatraya Uttam Ukale, Petri Tähtinen, Tuomas Lönnberg
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2020
Journal: Chemistry - A European Journal
Journal acronym: CHEM-EUR J
Volume: 26
Issue: 10
First page : 2164
Last page: 2168
Number of pages: 5
ISSN: 0947-6539
eISSN: 1521-3765
DOI: https://doi.org/10.1002/chem.201905434
Web address : https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201905434
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/46030720
A C-nucleoside with 6-phenyl-1H-carbazole as the base moiety has been synthesized and incorporated in the middle of an oligonucleotide. Mercuration of this modified residue at positions 1 and 8 gave the first example of an oligonucleotide featuring a monofacial dinuclear organometallic nucleobase. The dimercurated oligonucleotide formed stable duplexes with unmodified oligonucleotides placing either cytosine, guanine, or thymine opposite to the organometallic nucleobase. A highly stabilizing (Delta T-m=7.3 degrees C) Hg-II-mediated base pair was formed with thymine. According to DFT calculations performed at the PDE0DH level of theory, this base pair is most likely dinuclear, with the two Hg-II ions coordinated to O2 and O4 of the thymine base.
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