A phototautomerizable model DNA base pair

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

Research output: Contribution to journalArticlepeer-review

82 Scopus citations

Abstract

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 (US)
Pages (from-to)9917-9920
Number of pages4
JournalJournal of the American Chemical Society
Volume122
Issue number41
DOIs
StatePublished - Oct 18 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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