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



: Dattatraya Uttam Ukale, Petri Tähtinen, Tuomas Lönnberg

Publisher: WILEY-V C H VERLAG GMBH

: 2020

: Chemistry - A European Journal

: CHEM-EUR J

: 26

: 10

: 2164

: 2168

: 5

: 0947-6539

: 1521-3765

DOI: https://doi.org/10.1002/chem.201905434

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

: 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.

Last updated on 2024-26-11 at 13:26