Jump to main content
Jump to site search

Issue 15, 2014
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements