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 journalArticle

82 Citations (Scopus)

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
Pages (from-to)9917-9920
Number of pages4
JournalJournal of the American Chemical Society
Volume122
Issue number41
DOIs
Publication statusPublished - Oct 18 2000

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Base Pairing
Proton transfer
DNA
Protons
Imines
Solvation
Molecular Dynamics Simulation
Amines
Molecular dynamics
Spectrum Analysis
Spectroscopy
Computer simulation
2-(2'-hydroxyphenyl)benzoxazole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ogawa, A. K., Abou-Zied, O. K., Tsui, V., Jimenez, R., Case, D. A., & Romesberg, F. E. (2000). A phototautomerizable model DNA base pair. Journal of the American Chemical Society, 122(41), 9917-9920. https://doi.org/10.1021/ja001778n

A phototautomerizable model DNA base pair. / Ogawa, A. K.; Abou-Zied, O. K.; Tsui, V.; Jimenez, R.; Case, D. A.; Romesberg, F. E.

In: Journal of the American Chemical Society, Vol. 122, No. 41, 18.10.2000, p. 9917-9920.

Research output: Contribution to journalArticle

Ogawa, AK, Abou-Zied, OK, Tsui, V, Jimenez, R, Case, DA & Romesberg, FE 2000, 'A phototautomerizable model DNA base pair', Journal of the American Chemical Society, vol. 122, no. 41, pp. 9917-9920. https://doi.org/10.1021/ja001778n
Ogawa AK, Abou-Zied OK, Tsui V, Jimenez R, Case DA, Romesberg FE. A phototautomerizable model DNA base pair. Journal of the American Chemical Society. 2000 Oct 18;122(41):9917-9920. https://doi.org/10.1021/ja001778n
Ogawa, A. K. ; Abou-Zied, O. K. ; Tsui, V. ; Jimenez, R. ; Case, D. A. ; Romesberg, F. E. / A phototautomerizable model DNA base pair. In: Journal of the American Chemical Society. 2000 ; Vol. 122, No. 41. pp. 9917-9920.
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