Isolation and Characterization of a Thymine-Lysine Adduct in UV-Irradiated Nuclei. The Role of Thymine-Lysine Photoaddition in Photo-Cross-Linking of Proteins to DNA

Journal of the American Chemical Society

Volumn 105, Issue 23, 1983, Pages 6989-6991

  Saito, Isao ^a   Sugiyama, Hiroshi ^a   Matsuura, Teruo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013170235     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00361a056     Document Type: Article

References (17)

1. Photoinduced Reactions. 151.
2. (a) Smith, K. C., Ed. “Aging, Carcinogenesis and Radiation Biology: The Role of Nucleic Acid Addition Reactions”; Plenum Press: New York, 1976. (b) Kornhauser, A. Photochem. Photobiol. 1976, 10, 411. (c) Smith, K. C. Photochem. Photobiol. Nucleic Acids 1976, 2, 187.
3. (a) Sperling, J.; Havron, A. Biochemistry 1976, 15, 1489. (b) Schimmel, P. R. Acc. Chem. Rees. 1977, 15, 1489. (c) Shetlar, M. D. Photochem. Photobiol. Rev. 1980, 5, 105.
4. Cao, T. M.; Sung, M.T. Biochemistry 1982, 21, 3419 and references therein.
5. Varghese, A. J. ref 2a, p. 207.
6. (a) Felsenfeld, G. Nature (London) 1978, 271, 115. (b) Johns, E. W. “Histones and Nucleohistones”; Phillips, D, M. P., Ed.; Plenum Press: New York, 1974: p. 66. (c) Ichimura, S.; Mita, K.; Zama M. Biochemistry 1982, 21, 5329 and references therein.
7. (a) Saito, I., Sugiyama, H.; Ito, S.; Furukawa, N.; Matsuura, T. J. Am. Chem. Soc. 1981, 103, 1598. (b) Saito, I.; Sugiyama, H.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 956.
8. Reverse-phase Nucleosil 7Cl8 column; acetonitrile-water (5:95); retention time 26 min at 4 mL/min.
9. Compound 3 was slowly converted to 2 in neutral or alkaline aqueous solution even at room temperature. Acidic solution of 3 rapidly produced 2 in almost quantitative yield.
10. Irradiation of 1 and 1-methylguanidine in aqueous alkaline solution did not produce any photoadduct.
11. Reverse-phase Nucleosil 7C18 column (1 X 25 cm); 0.5% aqueous acetic acid.
12. Rf 0.6 on silica gel TLC (iso-PrOH-30% ammonia-water, 7:1:2).
13. In fact, addition of NaCl (up to 2 M) to the reaction system considerably retarded the formation of 2 as compared to the control experiment.
14. Rill, R. L.; Shaw, B. R.; Van Holde, K. E. “Methods in Cell Biology”; Academic Press: New York, 1978; Vol. XVIII, p. 76. We are indebted to Professor M. Yanagida, Kyoto University, for providing us the sample.
15. (a) Strniste, G. E.; Rail, S.C. Biochemistry 1976, 15, 1712. (b) Martinson, H. G.; Shetlar, M. D.; McCarth, B. J. Biochemistry 1976, 15, 2002. (c) Sperling, J.; Sperling, R. Nucleic Acids Res. 1978, 5, 2755. (d) Mandel, R.; Kolomitjtseva, G.; Brahms, J. G. Eur. J. Biochem. 1979, 211, 1222. (e) Mee, L., K.; Adelstein, S. J. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2194.
16. Kunkel, G. R.; Martinson, H.G. Nucleic Acids Res. 1978, 5, 4263.
17. Saito, I.; Sugiyama, H.; Matsuura, T. Nucleic Acids Res. 1983, Sp. No 11, 225.