2019
DOI: 10.1021/acsomega.9b00089
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Effect of Triazole-Modified Thymidines on DNA and RNA Duplex Stability

Abstract: Previous reports showed that consecutive incorporations of triazole-modified 2′-deoxyuridines stabilized DNA•DNA and DNA•RNA duplexes due to additional πstacking between triazole moieties. In this work, several triazole-modified thymidines (1−3) have been synthesized via Cu-catalyzed azide−alkyne cycloaddition reaction and incorporated into oligodeoxyribonucleotides (ODNs). Compounds 1−3 decreased the stability of DNA•DNA and DNA• RNA duplexes. Among these triazole-modified thymidines, 3 with a coumarin-modifi… Show more

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Cited by 2 publications
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“…vancomycin moiety led to a rather significant destabilization of the duplex (ΔTm = −3.9 °C) compared to that of the unmodified dsDNA (62.7 ± 0.3 °C compared to 66.6 ± 0.1 °C). This destabilization might be caused either by the presence of the bulky vancomycin moiety since other large moieties such as polyethylene glycol [56] induced similar decreases in Tm values, or by the thermal penalty imparted by the introduction of a single triazole-containing nucleotide [57][58][59]. Nonetheless, this UV-melting analysis indicates that the modification did not significantly interfere with duplex formation.…”
Section: Biochemical Characterization Of the Modified Nucleotide Dumentioning
confidence: 83%
“…vancomycin moiety led to a rather significant destabilization of the duplex (ΔTm = −3.9 °C) compared to that of the unmodified dsDNA (62.7 ± 0.3 °C compared to 66.6 ± 0.1 °C). This destabilization might be caused either by the presence of the bulky vancomycin moiety since other large moieties such as polyethylene glycol [56] induced similar decreases in Tm values, or by the thermal penalty imparted by the introduction of a single triazole-containing nucleotide [57][58][59]. Nonetheless, this UV-melting analysis indicates that the modification did not significantly interfere with duplex formation.…”
Section: Biochemical Characterization Of the Modified Nucleotide Dumentioning
confidence: 83%