5-Cyanoimino-4-oxomethylene-4,5-dihydroimidazole and 5-cyanoamino-4- imidazolecarboxylic acid intermediates in nitrosative guanosine deamination: Evidence from 18O-labeling experiments

Journal of the American Chemical Society

Volumn 126, Issue 32, 2004, Pages 9960-9969

  Rayat, Sundeep ^a   Majumdar, Papiya ^a   Tipton, Peter ^b   Glaser, Rainer ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; EXPERIMENTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRATION; REACTION KINETICS;

ISOTOPIC SHIFTS; REACTION PRODUCTS;

CARBOXYLIC ACIDS;

5 CYANOAMINO 4 IMIDAZOLECARBOXYLIC ACID; 5 CYANOIMINO 4 OXOMETHYLENE 4,5 DIHYDROIMIDAZOLE; CARBOXYLIC ACID DERIVATIVE; DNA BASE; GUANOSINE; IMIDAZOLE DERIVATIVE; OXANOSINE; OXYGEN 18; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEAMINATION; NITROSATION; REACTION ANALYSIS;

DEAMINATION; DNA; GUANOSINE; IMIDAZOLES; ISOTOPE LABELING; NITRITES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXYGEN ISOTOPES; PYRIMIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 4043059199     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049835q     Document Type: Article

References (91)

1. (a) Guanine: Strecker, A. Ann. 1861, 118, 151-177.
2. (b) Adenine: Kossel, A. Ber. 1865, 85, 1928-1930.
3. (c) Adenine: Kossel, A. Z. Physiol. Chem. 1888, 121, 241-253.
4. (d) Cytosine: Kossel, A.; Steudel, H. Z. Physiol. Chem. 1903, 38, 49-59.
5. (a) Gierer, A.; Mundry, K. W. Nature 1958, 182, 1457-1458.
6. (b) Schuster, H.; Schramm, G. Z. Naturforsch. B 1958, 13, 697-704.
7. (c) Geiduschek, E. P. Proc. Natl. Acad. Sci. U.S.A. 1961, 47, 950-955.
8. (d) Horn, E. E.; Herriott, R. M. Proc. Natl. Acad. Sci. U.S.A. 1962, 48, 1409-1416.
9. Schuster, V. H.; Wilhelm, R. C. Biochim. Biophys. Acta 1963, 68, 554-560.
10. Duncan, B. K.; Miller, J. H. Nature 1980, 287, 560-561.
11. Viswanathan, A.; You, H. J.; Doetsch, P. W. Science 1999, 284, 159-162.
12. (a) Nair, V.; Richardson, S. G. Tetrahedron Lett. 1979, 1181-1184.
13. (b) Nair, V.; Richardson, S. G. J. Org. Chem. 1980, 45, 3969-3974.
14. (c) Nair, V.; Chamberlain, S. D. Synthesis 1984, 401-403.
15. (a) Ignarro, L. J. Annu. Rev. Pharmacol. Toxicol. 1990, 30, 535-560.
16. (b) Schuman, E. M.; Madison, D. V. Science 1991, 254, 1503-1506.
17. Wink, P. A.; Kasprzak, K. S.; Maragos, C. M.; Elespuru, R. K.; Misra, M.; Dunams, T. M.; Cebula, T. A.; Koch, W. H.; Andrews, A. W.; Allen, J. S.; Keefer, L. K. Science 1991, 254, 1001-1003.
18. (a) Geiduschek, E. P. Biochemistry 1961, 47, 950-955.
19. (b) Geiduschek, E. P. J. Mol. Biol. 1962, 4, 467-487.
20. (c) Becker, E. F.; Zimmerman, B. K.; Geiduschek, E. P. J. Mol. Biol. 1964, 8, 377-391.
21. (d) Becker, E. F. Biochim. Biophys. Acta 1967, 142, 238-244.
22. (a) Caulfield, J. L.; Wishnok, J. S.; Tannenbaum, S. Chem. Res. Toxicol. 2003, 16, 571-574.
23. (b) Burney, S.; Caulfield, J. L.; Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. Mutat. Res. 1999, 424, 37-49.
24. (a) Shaprio, R.; Dubelman, S.; Feinberg, A. M.; Crain, P. F.; McCloskey, J. A. J. Am. Chem. Soc. 1977, 99, 302-303.
25. (b) Dubelman, S.; Shaprio, R. Nucleic Acids Res. 1977, 4, 1815-1827.
26. (a) Kirchner, J. J.; Hopkins, P. B. J. Am. Chem. Soc. 1991, 113, 4681-4682.
27. (b) Kirchner, J. J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1992, 114, 4021-4027.
28. (c) Harwood, E. A.; Sigurdsson, S. T.; Edfelt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
29. Committee on Nitrite and Alternative Curing Agents in Food. The Health Effect of Nitrate, Nitrite, and N-nitroso Compounds; National Academy Press: Washington, D.C., 1981.
30. Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1152.
31. Wood, R. D.; Mitchell, M.; Sgouros, J.; Lindahl, T. Science 2001, 291, 1284-1289.
32. Lindahl, T.; Wood, R. D. Science 1999, 286, 1897-1905.
33. Rouse, J.; Jachson, S. P. Science 2002, 297, 547-551.
34. International Union of Pure and Applied Chemistry, Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. World Wide Web material by G. P. Moss at URL http://www.chem.qmul.ac.uk/iupac. (a) Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure, Section Nucleic Acids and Component Units. (b) Nomenclature for Isotopically Substituted Compounds and Specifically Labeled Compounds: Section H-2, Names for Isotopically Modified Compounds.
35. (a) Tannenbaum, S. R.; Tamir, S.; Rojas-Walker, T. D.; Wishnok, J, S. In Nitrosamines and Related N-Nitroso Compounds-Chemistry and Biochemistry; Loeppky, R. N., Michejda, C. L., Eds. ACS Symposium Series 553; American Chemical Society: Washington, D.C., 1994, Chapter 10, pp 120-135.
36. (b) Lewis, R. S.; Tannenbaum, S. R.; Deen, W. M. J. Am. Chem. Soc. 1995, 117, 3933-3939.
37. (c) Challis, B. C.; Kyrtopoulos, S. A. J. Chem. Soc., Perkin Trans. 2 1978, 2, 1296.
38. (d) Mirvish, S. S. Toxicol. Appl. Pharmacol. 1975, 31, 325-351.
39. (a) Suzuki, T.; Yamaoka, R.; Nishi, M.; Ide, H.; Makino, K. J. Am. Chem. Soc. 1996, 118, 2515-2516.
40. (b) Suzuki, T.; Matsumura, Y.; Ide, H.; Kanaori, K.; Tajima, K.; Makino, K. Biochemistry. 1997, 36, 8013-8019.
41. Lucas, L. T.; Gatehouse, D.; Shukar, D. E. G. J. Biol. Chem. 1999, 274, 18319-18326.
42. (a) Glaser, R.; Son, M.-S. J. Am. Chem. Soc. 1996, 118, 10942-10943.
43. (b) Glaser, R.; Rayat, S.; Lewis, M.; Son, M.-S.; Meyer, S. J. Am. Chem. Soc. 1999, 121, 6108-6119.
44. More recent studies revealed that pyrimidine ring opening also may play a role in the deaminations of adenine and cytosine. (a) Hodgen, B.; Rayat, S.; Glaser, R. Org. Lett. 2003, 5, 4077-4080.
45. (b) Rayat, S. Ph.D. Dissertation, University of Missouri-Columbia, 2003.
46. (a) Glaser, R.; Horan, C. J. J. Org. Chem. 1995, 60, 7518-7528.
47. (b) Glaser, R.; Horan, C. J.; Zollinger, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2210-2213.
48. (c) Glaser, R.; Horan, C. J.; Lewis, M.; Zollinger, H. J. Org. Chem. 1999, 64, 902-913.
49. Rayat, S.; Glaser, R. J. Org. Chem. 2003, 68, 9882-9892.
50. Glaser, R.; Lewis, M. Org. Lett. 1999, 1, 273-276.
51. Rayat, S.; Wu, Z.; Glaser, R. Chem. Res. Toxicol. 2004, 17, in press.
52. (a) Suzuki, T.; Ide, H.; Yamada, M.; Endo, N.; Kanaori, K.; Tajima, K.; Morii, T.; Makino, K. Nucleic Acids Res. 2000, 28, 544-551.
53. (b) Suzuki, T.; Kanaori, K.; Makino, K. Nucleic Acids Syrup. Ser. 1997, 37, 313-314.
54. (a) Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273-279.
55. (b) Seikaly, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-613.
56. Hydrolysis of cyanoamine and of its carbodiimide tautomer: (a) Tordini, F.; Bencini, A.; Bruschi, M.; Dr Gioia, L.; Zampella, G.; Fantucci, P. J. Phys. Chem A 2003, 107, 1188-1196.
57. (b) Lewis, M.; Glaser, R. Chem. Eur. J. 2002, 8, 1934-1944.
58. (c) Lewis, L.; Glaser, R. J. Am. Chem. Soc. 1998, 120, 8541-8542.
59. Wu, Z.; Glaser, R. Unpublished results.
60. (a) Ye, Y.; Muller, J. G.; Luo, W.; Mayne, C. L.; Shallop, A. J.; Jones, R. A,; Burrows, C. J. J. Am. Chem. Soc. 2003, 125, 13926-13927.
61. (b) Novak, M.; Nguyen, T.-M. J. Org. Chem. 2003, 68, 9875-9881.
62. (c) Haiss, P.; Zeller, K.-P. Angew. Chem., Int. Ed. 2003, 42, 303-305.
63. (d) Peller, J.; Wiest, O.; Kamat, P. V. Chem. Eur. J. 2003, 9, 5379-5387.
64. (a) Buckler, K. U.; Haase, A. R.; Lutz, O.; Muler, M.; Nolle, A. Z.; Z. Naturforsch. A 1977, 32, 126-130.
65. (b) Webb, D. R.; McDonald, G. G.; Trentham, D. R. J. Biol. Chem. 1978, 253, 2908-2911.
66. (c) Bock, J.; Cohn, M. J. Biol. Chem. 1978, 253, 4082-4085.
67. (d) Cohn, M.; Hu, A. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 200-203.
68. (e) Van Etten, R. L.; Risley, J. M. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 4784-4787.
69. (f) Jarvest, R. L.; Lowe, G. J. Chem. Soc., Chem. Commun. 1979, 364-366.
70. (g) Cohn, M.; Rao, B. D. N. Bull. Magn. Reson. 1979, 38-60.
71. (h) Risley, J. M.; Van Etten, R. L. J. Am. Chem. Soc. 1978, 101, 252-253.
72. Jameson, C. J. J. Chem. Phys. 1977, 66, 4983-4988.
73. Risley, J. M.; Van Etten, R. L. In Isotope Efects in NMR Spectroscopy; Diehl, P., Fluck, E., Guenther, H., Kosfeld, R., Selig, J., Eds.; Springer-Verlag: Berlin, 1990; NMR 22, pp 83-168.
74. Isotopic shift in an 180-labeled sugar of adenosine: Jiang, C.; Suhadolnik, R. J.; Baker, D. C. Nucleosides Nucleotides 1988, 7, 271-294.
75. Rodríguez-Casado, A.; Carmona, P.; Molina M. J. Phys. Chem. B 1998, 102, 5387-5393.
76. (a) Heppel, L. A.; Hurwitz, J.; Horecker, B. L. J. Am. Chem. Soc. 1957, 79, 630-633.
77. (b) Chassy, B. M.; Suhadolnik, R. J. J. Biol. Chem. 1967, 242, 3655-3658.
78. (c) Weiss, P. M.; Cook, P. F.; Hermes, J. D.; Cleland, W. W. Biochemistry 1987, 26, 7378-7384.
79. (d) Bhaumik, D.; Medin, J.; Gathy, K.; Coleman, M. S. J. Biol. Chem. 1993, 268, 5464-5470.
80. (e) Shih, P.; Wolfenden, R. Biochemistry, 1996, 35, 4697-4703
81. (f) Wolfenden, R.; Kaufman, J.; Macon, J. B. Biochemistry 1969, 8, 2412-2415.
82. (g) Bär, H. P.; Drummond, G. I. BBRC 1966, 24, 584-587.
83. (a) Benzoic acid: Furic, K.; Colombo, L. J. Raman Spectrosc. 1986, 17, 23-27.
84. (b) Overview: Allinger, N. L.; Zhu, Z. Q. S.; Chen, K. J. Am. Chem. Soc. 1992, 114, 6120-6133.
85. Niitsuma, S.; Kato, K.; Takita, T.; Umezawa, H. Tetrahedron Lett. 1985, 26, 5785-5786.
86. Dunbar, R. E.; White, G. C. J. Org. Chem. 1958, 23, 915-916.
87. Qian, M.; Glaser, R. J. Am. Chem. Soc. 2004, 126, 2274-2275.
88. Luk, K.-C.; Moore, D. W.; Keith, D. D. Tetrahedron Lett. 1994, 35, 1007-1010.
89. Bergman, J.; Stalhandske, C. Tetrahedron 1996, 52, 753-770.
90. Hammen, P. D.; Allen, D. J. M. J. Heterocycl. Chem. 1987, 24, 1701-1703.
91. Lefebvre, A.; Bernier, J.-L.; Lespagnol, C. J. Heterocycl. Chem. 1976, 13, 167-168.