Premium
1,8‐Dimercuri‐6‐Phenyl‐1 H ‐Carbazole as a Monofacial Dinuclear Organometallic Nucleobase
Author(s) -
Ukale Dattatraya Uttam,
Tähtinen Petri,
Lönnberg Tuomas
Publication year - 2020
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.201905434
Subject(s) - nucleobase , thymine , oligonucleotide , moiety , chemistry , carbazole , cytosine , guanine , stereochemistry , nucleoside , group 2 organometallic chemistry , photochemistry , nucleotide , molecule , dna , organic chemistry , biochemistry , gene
A C ‐nucleoside with 6‐phenyl‐1 H ‐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 (Δ T m =7.3 °C) Hg II ‐mediated base pair was formed with thymine. According to DFT calculations performed at the PBE0DH 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.