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Oligonucleotides Incorporating Palladacyclic Nucleobase Surrogates
Author(s) -
Maity Sajal Kumar,
Lönnberg Tuomas
Publication year - 2018
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.201705797
Subject(s) - nucleobase , oligonucleotide , moiety , chemistry , stereochemistry , residue (chemistry) , dna , base pair , ligand (biochemistry) , crystallography , organic chemistry , biochemistry , receptor
An oligonucleotide incorporating a palladacyclic nucleobase has been prepared by ligand‐directed metalation of a phenylpyridine moiety. This oligonucleotide hybridized with natural counterparts placing any of the canonical nucleobases opposite to the palladacyclic residue. The palladated duplexes had B‐type conformation and melting temperatures comparable to those of respective unmodified duplexes with a single mismatch. In the duplexes placing C, G or T (but not A) opposite to the palladacyclic residue, greatly increased absorptivity suggested formation of a Pd II ‐mediated base pair. Absorptivity and ellipticity of these duplexes persisted even at the highest temperatures applicable in T m and CD experiments (90 °C). Evidently the Pd II ‐mediated base pairs do not dissociate under the experimental conditions.