Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides post-synthetic trifluoromethyl conversion

Post-synthetic conversion of the trifluoromethyl group to a heteroaryl group at the C5 position of the pyrimidine base in DNA oligonucleotides was achieved. Specifically, the oligonucleotides containing 5-trifluoromethylpyrimidine bases were treated with o -phenylenediamines and o -aminothiophenols...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-05, Vol.22 (17), p.351-3517
Main Authors: Ito, Yuta, Tanaka, Hisato, Murakami, Ayana, Fuchi, Yasufumi, Hari, Yoshiyuki
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Post-synthetic conversion of the trifluoromethyl group to a heteroaryl group at the C5 position of the pyrimidine base in DNA oligonucleotides was achieved. Specifically, the oligonucleotides containing 5-trifluoromethylpyrimidine bases were treated with o -phenylenediamines and o -aminothiophenols as nucleophiles to afford the corresponding 5-(benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine-modified bases. Furthermore, evaluation of the fluorescence properties of the obtained oligonucleotides revealed that among them the oligonucleotide containing 5-(5-methylbenzimidazol-2-yl)cytosine exhibited the highest fluorescence intensity. These results indicated that post-synthetic trifluoromethyl conversion, which is practical and operationally simple, is a powerful tool for exploring functional oligonucleotides. 5-(Benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine bases-modified oligonucleotides were prepared by post-synthetic trifluoromethyl conversion and their fluorescence properties were measured.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00402g