Reaction of O6-Alkylguanine-DNA Alkyltransferase with O6-Methylguanine Analogues: Evidence That the Oxygen of O6-Methylguanine is Protonated by the Protein To Effect Methyl Transfer

Biochemistry

Volumn 31, Issue 14, 1992, Pages 3688-3694

  Spratt, Thomas E ^a   De Los Santos, Hannah ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 O ALKYLGUANINE DNA ALKYLTRANSFERASE; 6 O METHYLGUANINE; CYSTEINE; GUANINE; METHYL GROUP; NITROGEN; OXYGEN; PROMUTAGEN; SELENIUM; SULFUR; DRUG DERIVATIVE; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; METHYLTRANSFERASE; O (6) METHYLGUANINE; O(6) METHYLGUANINE DNA METHYLTRANSFERASE; O-(6)-METHYLGUANINE; PROTON;

ARTICLE; CHEMICAL REACTION KINETICS; DNA REPAIR; ENZYME SUBSTRATE COMPLEX; ISOTOPE LABELING; MICHAELIS MENTEN KINETICS; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SCINTILLATION SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; KINETICS; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ESCHERICHIA COLI; GUANINE; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; METHYLTRANSFERASES; O(6)-METHYLGUANINE-DNA METHYLTRANSFERASE; OXYGEN; PROTONS; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0026611085     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi00129a018     Document Type: Article

References (61)

1. Balsiger, R. W., & Montgomery, J. A. (1960) J. Org. Chem. 25, 1573-1575.
2. Bhattacharyya, D., Tano, K., Bunick, G. J., Uberbacher, E. C., Behnke, W. D., & Mitra, S. (1988) Nucleic Acids Res. 16, 6397-6410.
3. Chan, C. L., Wu, Z., Eastman, A., & Bresnick, E. (1990) Carcinogenesis 11, 1217-1221.
4. Chu, S.-H. (1971) J. Med. Chem. 14, 254-255.
5. Cook, P. D., Rousseau, R. J., Mian, A. M., Meyer, R. B., Jr., Dea, P., Ivanovics, G., Streeter, D. G., Witkowski, J. T., Stout, M. G., Simon, L. N., Sidwell, R. W., & Robins, R. K. (1975) J. Am. Chem. Soc. 97, 2916-2917.
6. Cook, P. D., Rousseau, R. J. Mian, A. M., Dea, P., Meyer, R. B., Jr., & Robins, R. K. (1976) J. Am. Chem. Soc. 98, 1492-1498.
7. Davoll, J. (1960) J. Chem. Soc., 131-138.
8. Demple, B. (1990) in Protein Methylation (Paik, W. M., Kim, S., Eds.) pp 285-304, CRC Press, Inc., Boca Raton, FL.
9. Demple, B., Jacobsson, A., Olsson, M., Robins, P., & Lindahl, T. (1982) J. Biol. Chem. 257, 13776-13780.
10. Demple, B., Sedgwick, B., Totty, N., Waterfield, M. D., & Lindahl, T. (1985) Proc. Natl. Acad. Sci. U.S.A. 82, 2688-2692.
11. Dolan, M. E., Morimoto, K., & Pegg, A. E. (1985) Cancer Res. 45, 6413-6417.
12. Dolan, M. E., Moschel, R. C., & Pegg, A. E. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 5368-5372.
13. Fahti, R., Goswami, B., Kung, P.-P., Gaffney, B., & Jones, R. A. (1990) Tetrahedron Lett. 31, 319-320.
14. Foote, R. S., Mitra, S., & Pal, B. C. (1980) Biochem. Biophys. Res. Commun. 97, 654-659.
15. Gaffney, B. L., & Jones, R. A. (1982) Tetrahedron Lett. 23, 2253-2256.
16. Gorton, B. S., & Shive, W. (1957) J. Am. Chem. Soc. 79, 670-672.
17. Graves, R. J., Li, B. F. L., & Swann, P. F. (1989) Carcinogenesis 10, 661-666.
18. Hora, J. F., Eastman, A., & Bresnick, E. (1983) Biochemistry 22, 3759-3763.
19. Karran, P., Lindahl, T., & Griffin, B. (1979) Nature 280, 76-77.
20. Laemmli, U. K. (1970) Nature 227, 680-685.
21. Lindahl, T. (1982) Annu. Rev. Biochem. 51, 61-87.
22. Margison, G. P., Cooper, D. P., & Potter, P. M. (1990) Mutat. Res. 233, 15-21.
23. Markees, D. G., & Kidder, G. W. (1956) J. Am. Chem. Soc. 78, 4130-4135.
24. Mautner, H. G. (1956) J. Am. Chem. Soc. 78, 5292-5294.
25. McCarthy, T. V., & Lindahl, T. (1985) Nucleic Acids Res. 13, 2683-2698.
26. Merril, C. R., Goldman, D., Sedman, S. A., & Ebert, M. H.(1981) Science 211, 1437-1438.
27. Mitsunobu, O. (1981) Synthesis 1, 1981.
28. Montgomery, J. A., & Wood, N. F. (1964) J. Org. Chem. 29, 734-738.
29. Morimoto, K., Dolan, M. E., Scicchitano, D., & Pegg, A. E. (1985) Carcinogenesis 6, 1027-1031.
30. Myers, G. M., & Sancar, A. (1989) Chem. Res. Toxicol. 2, 197-226.
31. Nakabeppu, Y., Kondo, H., Kawabata, S., Iwanaga, S., & Sekiguchi, M. (1985) J. Biol. Chem. 260, 7281-7288.
32. Olsson, M., & Lindahl, T. (1980) J. Biol. Chem. 255, 10569-10571.
33. Pegg, A. E. (1984) Cancer Invest. 2, 223-231.
34. Pegg, A. E. (1990) Cancer Res. 50, 6119-6129.
35. Pegg, A. E., Wiest, L., Foote, R. S., Mitra, S., & Perry, W. (1983) J. Biol. Chem. 258, 2327-2333.
36. Pegg, A. E., Scicchitano, D., & Dolan, M. E. (1984) Cancer Res. 44, 3806-3811.
37. Perrella, F. W. (1988) Anal. Biochem. 174, 437-447.
38. Potter, P. M., Wilkinson, M. C., Fitton, J., Brennand, J., Cooper, D. P., & Margison, G. P. (1987) Nucleic Acids Res. 15, 9177-9193.
39. Rebeck, G. W., Coons, S., Carroll, P., & Samson, L. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 3039-3043.
40. Revankar, G. R., Gupta, P. K., Adams, A. D., Dailey, N. K., McKernan, P. A., Cook, P. D., Canonico, P. G., & Robins, R. K. (1984) J. Med. Chem. 27, 1389-1396.
41. Robins, R. K., Horner, J. K., Greco, C. V., Noell, C. W., & Beames, C. G., Jr. (1963) J. Org. Chem. 28, 3041-3046.
42. Ryberg, B., Hall, J., & Karran, P. (1990) Nucleic Acids Res. 18, 17-21.
43. Scicchitano, D., & Pegg, A. E. (1982) Biochem. Biophys. Res. Commun. 109, 995-1001.
44. Scicchitano, D., Jones, R. A., Kuzmich, S., Gaffney, B., Lasko, D. D., Essigmann, J. M., & Pegg, A. E. (1986) Carcinogenesis 7, 1383-1386.
45. Sedgwick, B. (1983) Mol. Gen. Genet. 191, 466-472.
46. Sedgwick, B., Robins, P., Totty, N., & Lindahl, T. (1988) J. Biol. Chem. 263, 4430-4433.
47. Seela, F., Kehne, A., & Winkeler, H.-D. (1983) Liebigs Ann. Chem., 137-146.
48. Smith, R. H., Jr., Koepke, S. R., Tondeur, Y., Denlinger, C. L., & Michejda, C. J. (1985) J. Chem. Soc., Chem. Commun., 936-937.
49. Souliotis, V. L., Giannopoulos, A., Koufakis, I., Kaila, S., Dimopoulos, C., & Kyrtopoulos, S. A. (1989) Carcinogenesis 10, 1203-1208.
50. Spector, T. (1978) Anal. Biochem. 86, 248-254.
51. Takano, K., Nakabeppu, Y., & Sekiguchi, M. (1988) J. Mol. Biol. 201, 261-271.
52. Tano, K., Bharracharyya, D., Foote, R. S., Mural, R. J., & Mitra, S. (1988) J. Bacteriol. 171, 1535-1543.
53. Temple, C., Jr., Smith, B. H., Kussner, C. L., & Montgomery, J. A. (1976) J. Org. Chem. 41, 3784-3788.
54. von Wronski, M. A., Shiota, S., Tano, K., Mitra, S., Bigner, D. D., & Brent, T. P. (1991) J. Biol. Chem. 266, 1064-1070.
55. Walsh, C. T. (1977) Horiz. Biochem. Biophys. 3, 36-81.
56. Weinfeld, M., Drake, A. F., Saunders, J. K., & Paterson, M. C. (1985) Nucleic Acids Res. 13, 7067-7077.
57. Wilkinson, M. C., Potter, P. M., Cawkwell, L., Georgradis, P., Patel, D., Swann, P. F., & Margison, G. P. (1989) Nucleic Acids Res. 17, 8475-8483.
58. Wilkinson, M. C., Cooper, D. P., Southan, C., Potter, P. M., & Margison, G. P. (1990) Nucleic Acids Res. 18, 13-16.
59. Yarosh, D. B. (1985) Mutat. Res. 145, 1-16.
60. Yarosh, D. B., Fornace, A. J., & Day, R. S., III (1985) Carcinogenesis 6, 949-953.
61. Yarosh, D. B., Hurst-Calderone, S., Babich, M. A., & Day, R. S., III (1986) Cancer Res. 46, 1663-1668.