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Tolerance of N2-heteroaryl modifications on guanine bases in a DNA G-quadruplex

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Abstract

To systematically determine the effect of N2-heteroaryl modification on the stability of G-quadruplex structures, six types of N2-heteroarylated deoxyguanosines were incorporated into oligonucleotides with intramolecular quadruplex-forming sequences obtained from the human telomere sequence. A UV melting experiment, electrophoretic mobility shift assay, and circular dichroism were performed to evaluate the influence of N2-heteroaryl modification. Among the N2-heteroaryl modifications used in this study, N2-(pyrimidin-2-yl) modification markedly destabilized the G-quadruplex structure. Interestingly, N2-heteroaryl modification in the middle guanine base of the fourth strand was well-tolerated and formed a G-quadruplex, suggesting that the fourth strand is the least important strand in sustaining the G-quadruplex structure.

Graphical abstract: Tolerance of N2-heteroaryl modifications on guanine bases in a DNA G-quadruplex

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Publication details

The article was received on 14 Dec 2018, accepted on 28 Dec 2018 and first published on 04 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03100B
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Tolerance of N2-heteroaryl modifications on guanine bases in a DNA G-quadruplex

    Y. Masaki, T. Inde, A. Maruyama and K. Seio, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03100B

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