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Updated: Jun 21, 2026

DNAzyme 10-23 - Based Nanomachines for Nucleic Acid Recognition
Published on: February 9, 2024
8-Aza-2'-deoxyguanosine: base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in
Frank Seela1, Dawei Jiang, Kuiying Xu
1Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany. Frank.Seela@uni-osnabrueck.de
Abstract:
Oligodeoxyribonucleotides containing 8-aza-2-deoxyguanosine 9 were synthesized and a new phosphoramidite 11, showing a high coupling yield in solid-phase synthesis, was prepared. Nucleoside 9 was found to be a perfect shape mimic of dG; it forms a strong base pair with dC and shows an excellent mismatch discrimination. Nucleoside 9 appears strongly fluorescent as the anion, and thus, it has unique reporter group properties as a replacement for dG. The pKa-value of 9 (8.4) is lower than that of dG (9.3) and increases from the single-stranded DNA (8.8) to duplex DNA (9.1). The fluorescence of the nucleoside 9 anion is decreased in ss-oligonucleotides and further reduced in duplex DNA. When mismatches of 9 are formed with the four DNA canonical bases, the fluorescence of mismatches is significantly higher than that of the perfectly paired duplex. The fluorescence of the nucleoside 9 anion correlates with the base pair stability.
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