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1,3,9‐Triaza‐2‐oxophenoxazine: An Artificial Nucleobase Forming Highly Stable Self‐Base Pairs with Three Ag I Ions in a Duplex
Author(s) -
Fujii Akane,
Nakagawa Osamu,
Kishimoto Yuki,
Okuda Takumi,
Nakatsuji Yusuke,
Nozaki Natsumi,
Kasahara Yuuya,
Obika Satoshi
Publication year - 2019
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.201900373
Subject(s) - nucleobase , metal ions in aqueous solution , electrospray ionization , tap water , ion , duplex (building) , chemistry , metal , base pair , dna , nucleic acid , analytical chemistry (journal) , crystallography , chromatography , organic chemistry , biochemistry , environmental engineering , engineering
Metal‐mediated base pairs (MMBPs) formed by natural or artificial nucleobases have recently been developed. The metal ions can be aligned linearly in a duplex by MMBP formation. The development of a three‐ or more‐metal‐coordinated MMBPs has the potential to improve the conductivity and enable the design of metal ion architectures in a duplex. This study aimed to develop artificial self‐bases coordinated by three linearly aligned Ag I ions within an MMBP. Thus, artificial nucleic acids with a 1,3,9‐triaza‐2‐oxophenoxazine (9‐TAP) nucleobase were designed and synthesized. In a DNA/DNA duplex, self‐base pairs of 9‐TAP could form highly stable MMBPs with three Ag I ions. Nine equivalents of Ag I led to the formation of three consecutive 9‐TAP self‐base pairs with extremely high stability. The complex structures of 9‐TAP MMBPs were determined by using electrospray ionization mass spectrometry and UV titration experiments. Highly stable self‐9‐TAP MMBPs with three Ag I ions are expected to be applicable to new DNA nanotechnologies.