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Issue 15, 2014
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Photoinduced changes in hydrogen bonding patterns of 8-thiopurine nucleobase analogues in a DNA strand

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Abstract

Hydrogen bonds (H-bonds) formed between nucleobases play an important role in the construction of various nucleic acid structures. The H-donor and H-acceptor pattern of a nucleobase is responsible for selective and correct base pair formation. Herein, we describe an 8-thioadenine nucleobase analogue and an 8-thiohypoxanthine nucleobase analogue with a photolabile 6-nitroveratryl (NV) group on the sulfur atom (SANV and SHNV, respectively). Light-triggered removal of the NV group causes tautomerization and a change in the H-bonding pattern of SANV and SHNV. This change in the H-bonding pattern has a strong effect on base recognition by 8-thiopurine nucleobase analogues. In particular, base recognition by SHNV is clearly shifted from guanine to adenine upon photoirradiation. These results show that a photoinduced change in the H-bonding pattern is a unique strategy for manipulating nucleic acid assembly with spatiotemporal control.

Graphical abstract: Photoinduced changes in hydrogen bonding patterns of 8-thiopurine nucleobase analogues in a DNA strand

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Publication details

The article was received on 05 Dec 2013, accepted on 13 Feb 2014 and first published on 13 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42427H
Citation: Org. Biomol. Chem., 2014,12, 2468-2473
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    Photoinduced changes in hydrogen bonding patterns of 8-thiopurine nucleobase analogues in a DNA strand

    K. Morihiro, T. Kodama, S. Mori and S. Obika, Org. Biomol. Chem., 2014, 12, 2468
    DOI: 10.1039/C3OB42427H

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