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- W2804313153 abstract "The α-anomers of 8-aza-2'-deoxyguanosine (αGd*) and 2'-deoxyguanosine (αGd) were site-specifically incorporated in 12-mer duplexes opposite to the four canonical DNA constituents dA, dG, dT, and dC. Oligodeoxyribonucleotides containing αGd* display significant fluorescence at slightly elevated pH (8.0). Oligodeoxyribonucleotides incorporating β-anomeric 8-aza-2'-deoxyguanosine (Gd*) and canonical dG were studied for comparison. For αGd* synthesis, an efficient purification of anomeric 8-azaguanine nucleosides was developed on the basis of protected intermediates, and a new αGd* phosphoramidite was prepared. Differences were observed for sugar conformations ( N vs S) and p Ka values of anomeric nucleosides. Duplex stability and mismatch discrimination were studied employing UV-dependent melting and fluorescence quenching. A gradual fluorescence change takes place in duplex DNA when the α-nucleoside αGd* was positioned opposite to the four canonical β-nucleosides. The strongest fluorescence decrease appeared in duplexes incorporating αGd*-Cd base pair matches. Decreasing fluorescence corresponds to increasing Tm values. For mismatch discrimination, the α-anomers αGd* and αGd are more efficient than the corresponding β-nucleosides. Duplexes with single purine-purine αGd*-αGd* or αGd-αGd base pairs are significantly more stable than those displaying β-d configuration. CD spectra indicate that single mutations by α-anomeric nucleosides do not affect the global structure of B-DNA." @default.
- W2804313153 created "2018-06-01" @default.
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- W2804313153 date "2018-05-17" @default.
- W2804313153 modified "2023-09-26" @default.
- W2804313153 title "Guanine and 8-Azaguanine in Anomeric DNA Hybrid Base Pairs: Stability, Fluorescence Sensing, and Efficient Mismatch Discrimination with α-<scp>d</scp>-Nucleosides" @default.
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- W2804313153 doi "https://doi.org/10.1021/acs.bioconjchem.8b00261" @default.
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