A1 Journal article – refereed

1,8-Dimercuri-6-Phenyl-1H-Carbazole as a Monofacial Dinuclear Organometallic Nucleobase

List of Authors: Dattatraya Uttam Ukale, Petri Tähtinen, Tuomas Lönnberg


Publication year: 2020

Journal: Chemistry - A European Journal

Journal acronym: CHEM-EUR J

Volume number: 26

Issue number: 10

Number of pages: 5

ISSN: 0947-6539

eISSN: 1521-3765

DOI: http://dx.doi.org/10.1002/chem.201905434

URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201905434

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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Last updated on 2021-09-08 at 10:12