Photoinduced reduction of thymine and uracil derivatives by hypophosphite: unusual high quantum yield of chromophore loss

Abstract

The quantum yield of chromophore loss of thymine, uracil and their corresponding nucleosides and nucleoside-5′- monophosphates undergoing irradiation with 254 nm UV light was found to be sharply enhanced by hypophosphite; thymine and uracil were reduced by hypophosphite to give 5,6-dihydrothymine and 5,6-dihydrouracil respectively.

References

1. J. Cadet and P. Vigny, Bioorganic Photochemistry, Photochemistry and Nucleic Acids, ed. M. Morrision, Wiley-Interscience, New York, 1989, vol. 1, pp 53–184; G. J. Fisher and H. E. Johns, Photochemistry and Photobiology of Nucleic Acids, ed. S. Y. Wang, Academic Press, New York, 1976, vol. 1, pp. 226–295; S. T. Reid, Advances in Heterocyclic Chemistry, ed. A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1982, vol. 30, pp. 278–291.
2. C. Sheu and C. S. Foote, J. Am. Chem. Soc., 1995, 117, 474 and refs. cited therein.
3. K. J. Wang, Ph.D. Thesis, 1995, Peking University, pp. 70–73.
4. K. J. Wang, X. M. Pan, J. L. Wu and W. Q. Wang, Photochem. Photobiol., 1997, 65, 656; K. J. Wang, Z. F. Chai and X. M. Pan, Origin Life Evol. Biosphere, 1998, in the press.
5. G. J. Fisher and H. E. Johns, Photochemistry and Photobiology of Nucleic Acids, ed. S. Y. Wang, Academic Press, New York, 1976, vol. 1, pp. 169–224; G. G. Gurzadyan and H. Gorner, Photochem. Photobiol., 1993, 58, 477; H. Gorner, J. Photochem. Photobiol. B: Biol., 1991, 10, 91; V. A. Ivanchenko, A. I. Titschenko, E. I. Budowsky, N. A. Simokova and N. S. Wulfson, Nucleic Acids Res., 1975, 2, 1365; G. G. Gurzadyan and H. Gorner, Photochem. Photobiol., 1994, 60, 323; G. G. Gurzadyan and H. Gorner, Photochem. Photobiol., 1996, 63, 143.
6. K. J. Wang and Z. F. Chai, J. Photochem. Photobiol. A: Chem., 1997, 107, 143.
7. A. M. Moore and C. H. Thomson, Can. J. Chem., 1957, 35, 163; A. M. Moore and C. H. Thomson, Science, 1955, 122, 594.
8. M. A. Herbert, L. C. LeBlanc and D. Weiblum, Photochem. Photobiol., 1969, 9, 33; R. B. Setlow, Biochim. Biophys. Acta, 1961, 49, 237.
9. I. H. Brown and H. E. Johns, Photochem. Photobiol., 1968, 8, 273.
10. R. D. Batt, K. Martin, J. M. Ploesser and J. Murphy, J. Chem. Soc., 1954, 3663; R. E. Cline and R. M. Fink, Anal. Chem., 1956, 28, 52; J. Varghese, Biochemistry, 1971, 10, 4283.