A phototautomerizable model DNA base pair

A.K. Ogawa, O.K. Abou-Zied, V. Tsui, R. Jimenez, D.A. Case, F.E. Romesberg, J. Am. Chem. Soc. (2000) 122:9917–9920.
pubpic2000ogawa2-(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.

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