PMID: 5257122Jun 1, 1969Paper

Excited-state two-proton tautomerism in hydrogen-bonded n-heterocyclic base pairs

Proceedings of the National Academy of Sciences of the United States of America
C al-TaylorMichael Kasha

Abstract

The optical absorption and luminescence spectra of 7-azaindole and its doubly hydrogen-bonded dimer were investigated as a model for the study of electronic interactions in DNA base pairs. It is demonstrated that a biprotonic phototautomerism occurs in the dimer and in suitable ethanol solvates in fluid solvents but that the phenomenon is not observed in a rigid solvent matrix. The normal violet structured fluorescence of 7-azaindole monomer becomes a broad green fluorescence in the tautomer. It is shown that spectral band interchanges, excimer formation, excited-state single-proton transfer, and proton tunneling cannot account for the luminescence change, but that the molecular exciton effect facilitates the cooperative two-proton reversible transfer. It is proposed that biprotonic phototautomerism with molecular environmental sensitivity could provide a mechanism for the initial step in ultraviolet mutagenic effects in DNA.

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Citations

Mar 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·A U Khan, M Kasha
Aug 6, 1996·Proceedings of the National Academy of Sciences of the United States of America·M ChattorajS G Boxer
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May 16, 2007·Proceedings of the National Academy of Sciences of the United States of America·Oh-Hoon Kwon, Ahmed H Zewail
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May 2, 2002·Proceedings of the National Academy of Sciences of the United States of America·Javier CatalánMichael Kasha
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