A phototautomerizable model DNA base pair

A. K. Ogawa, O. K. Abou-Zied, V. Tsui, R. Jimenez, D. A. Case, F. E. Romesberg*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

85 Citations (Scopus)


2-(2'-Hydroxyphenyl)benzoxazole (HBO) undergoes rapid photoinduced proton transfer from the enol-imine to the keto-amine tautomer. When incorporated in duplex DNA opposite an abasic site, HBO appears to be a good mimic of a natural DNA base pair based on duplex stability, UV and CD spectroscopy, and molecular dynamics simulations. In the chosen sequence context, HBO exists exclusively as the syn-enol tautomer, which is consistent with an environment of the model base that is dominated by neighboring nucleobases and not by solvation. The syn-enol efficiently undergoes photoinduced proton transfer to the keto-tautomer, which should allow for the study of tautomerization within the duplex DNA.

Original languageEnglish
Pages (from-to)9917-9920
Number of pages4
JournalJournal of the American Chemical Society
Issue number41
Publication statusPublished - Oct 18 2000
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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