Tautomerism in the guanyl radical

Journal of the American Chemical Society

Volumn 128, Issue 42, 2006, Pages 13796-13805

  Chatgilíaloglu, Chryssostomos ^a   Caminal, Clara ^a,c   Altieri, Alessio ^a   Vougioukalakis, Georgios C ^a,d,e   Mulazzani, Quinto G ^a   Gimisis, Thanasis ^b   Guerra, Maurizio ^a  

^a CNR   (Italy)

^b UNIVERSITY OF ATHENS   (Greece)

^c INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^d UNIVERSITY OF CRETE   (Greece)

^e California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; DESIGN FOR TESTABILITY; ELECTRON RESONANCE; ELECTRONS; HYDRATES; ISOMERIZATION; ISOMERS; RADIOLYSIS; REACTION KINETICS;

ELECTRON ADDUCTS; HALOGUANOSINES; PROTONATION; TRANSIENT SPECIES;

AMINES;

8 BROMOGUANINE; BROMINE; DEOXYGUANOSINE DERIVATIVE; GUANINE NUCLEOTIDE; GUANOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; MATHEMATICAL COMPUTING; OXIDATION; OXIDATION KINETICS; PROTON TRANSPORT; PULSE RADIOLYSIS; REACTION ANALYSIS; SPIN DENSITY DISTRIBUTION; SPIN LABELING; SUBSTITUTION REACTION;

EID: 33750378230     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062636h     Document Type: Article

References (85)

1. (a) Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111. 1094.
2. (b) Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 699.
3. Faraggi, M.; Klapper, M. H. J. Chim. Phys., Phys.-Chim. Biol. 1994, 91, 1062.
4. 5 which means that in principle these species can oxidize guanosine or 2-deoxyguanosine by one-electron transfer.
5. Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617.
6. -) = 1.90 V; see: Wardman, P. J. Phys. Chem. Ref. Data 1989, 14, 1637.
7. Kobayashi, K.; Tagawa, S. J. Am. Chem. Soc. 2003, 125, 10213.
8. Candeias, L. P.; Steenken, S. Chem.-Eur. J. 2000, 6, 475.
9. 7 See: (a) Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J.-L. J. Am. Chem. Soc. 1994, 116, 7403.
10. (b) Raoul, S.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Morin, B.; Weinfeld, M.; Cadet, J. J. Chem. Soc., Perkin Trans. 2 1996, 371.
11. (c) Gasparutto, D.; Ravanat, J.-L.; Gérat, O.; Cadet, J. J. Am. Chem. Soc. 1998, 120, 10283.
12. Ravanat, J.-L.; Saint-Pierre, C.; Cadet, J. J. Am. Chem. Soc. 2003, 125, 2030.
13. Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 2001, 123, 9681.
14. (a) Hole, E. O.; Nelson, W. H.; Sagstuen, E.; Close, D. M. Radiat. Res. 1992, 129, 119.
15. (b) Hole, E. O.; Nelson, W. H.; Close, D. M.; Sagstuen, E. J. Chem. Phys. 1987, 86, 5218.
16. Hole, E. O.; Sagstuen, E.; Nelson, W. H.; Close, D. M. Radiat. Res. 1992, 129, 1.
17. 11,12 The reported drawings in Scheme 1 are therefore chosen for a facile comprehension and the guanidine moieties are marked in red color.
18. Ioele, M.; Bazzanini, R.; Chatgilialoglu, C.; Mulazzani, Q. G. J. Am. Chem. Soc. 2000, 122, 1900.
19. Chatgilialoglu, C.; Caminal, C.; Guerra, M.; Mulazzani, Q. G. Angew. Chem., Int. Ed. 2005, 44, 6030.
20. De Champdoré, M.; De Napoli, L.; Montesarchio, D.; Piccialli, G.; Caminal, C.; Mulazzani, Q. G.; Navacchia, M. L.; Chatgilialoglu, C. Chem. Commun. 2004, 1756.
21. For selected recent papers on the excess electron transfer, see: (a) Wagenknecht, H.-A. Angew. Chem., Int. Ed. 2003, 42, 2454.
22. (b) Carell, T.; Behrens, C.; Gierlich, J. Org. Biomol. Chem. 2003, 1, 2221.
23. (c) Breeger, S.; Hennecke, U.; Carell, T. J. Am. Chem. Soc. 2004, 126, 1302.
24. (d) Ito, T.; Rokita, S. E. Angew. Chem., Int. Ed. 2004, 43, 1839.
25. (e) Giese, B.; Carl, B.; Carl, T.; Carell, T.; Behrens, C.; Hennecke, U.; Schiemann, O.; Feresin, E. Angew. Chem., Int. Ed. 2004, 43, 1848.
26. (f) T. Ito and S. E. Rokita, J. Am. Chem. Soc. 2004, 126, 15552.
27. (g) Wagner, C.; Wagenknecht, H.-A. Chem.-Eur. J. 2005, 11, 1871.
28. (h) Kaden, P.; Mayer-Enthart, E.; Trifonov, A.; Fiebing, T.; Wagenknecht, H.-A. Angew. Chem., Int. Ed. 2005, 44, 1636.
29. (i) Mayer-Enthart, E.; Kaden, P.; Wagenknecht, H.-A. Biochemistry 2005, 44, 11749.
30. Kimura, T.; Kawai, K.; Tojo, S.; Majima, T. J. Org. Chem. 2004, 69, 1169.
31. Manetto, A.; Breeger, S.; Chatgilialoglu, C.; Carell, T. Angew. Chem., Int. Ed. 2006, 45, 318.
32. (a) Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513.
33. (b) Ross, A. B.; Mallard, W. G.; Helman, W. P.; Buxton, G. V.; Huie, R. E.; Neta, P. NDRL-NIST Solution Kinetic Database, version 3; Notre Dame Radiation Laboratory: Notre Dame, IN and NIST Standard Reference Data, Gaithersburg, MD. 1998.
34. Wojnárovits, L.; Takács, E.; Dajka, K.; Emmi, S. S.; Russo, M.; D' Angelantonio, M. Radiat. Phys. Chem. 2004, 69, 217.
35. Hug, G. L. Nat. Stand. Ref. Data Ser., Nat. Bur. Stand. 1981, 69, 6.
36. 20
37. - with 1b. using a photoionization method and single concentration experiment: see: Arce, R.; Rivera, J. J. Photochem. Photobiol. A 1989, 49, 219.
38. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
39. For the reactivity of aromatic compounds towards hydrated electrons and related Hammett correlations, see: Anbar, M.; Hart, E. J. J. Am. Chem. Soc. 1964, 86, 5633.
40. The disappearance of the starting material or the appearance of the product (mol/kg) divided by the absorbed dose (1 Gy = 1 J/kg) gives the radiation chemical yield, i.e., G(-8) or G(1a). respectively.
41. The solution at pH ∼7 (i.e., natural without additives) before and after the irradiation dose of 2 kGy gave pH 7.6 and 5.7, respectively.
42. (a) Chatgilialoglu,. C.; Guerra, M.; Mulazzani, Q. G. J. Am. Chem. Soc. 2003, 125, 3839.
43. (b) Flyunt, R.; Bazzanini, R.; Chatgilialoglu, C.; Mulazzani, Q. G. J. Am. Chem. Soc. 2000, 122, 4225.
44. Jimenez, L. B.; Encinas, S.; Miranda, M. A.; Navacchia, M. L.; Chatgilialoglu, C. Photochem. Photobiol. Sci. 2004, 3, 1042.
45. Chatgilialoglu, C.; Ferreri, C.; Bazzanini, R.; Guerra, M.; Choi, S.-Y.; Emanuel, C. J.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2000, 122, 9525.
46. Compare transitions reported in Figures 6 and 8, and Tables S1 and S2.
47. Substitution of the hydrogen of the aminic group at N10 produces in the experimental spectrum the appearance of a new weak band above 800 nm (Figure 6) that is computed to occur at about 1000 nm at the TD-B3LYP/6-311G**/ /B1B95/6-31+G** level.
48. Gorb, L.; Leszczynski, J. J. Am. Chem. Soc. 1998, 120, 5024.
49. Llano, J.; Eriksson, L. A. Phys. Chem. Chem. Phys. 2004, 6, 4707.
50. 2NH-(-0.02).
51. For some reviews on hole migration through the stacked bases of duplex DNA. see: (a) Holmlin, R. E.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. 1997, 36, 2714.
52. (b) Kelley, S. O.; Barton, J. K. Science 1999, 283, 375.
53. (c) Grinstaff, M. W. Angew. Chem., Int. Ed. 1999, 38, 3629.
54. (d) Giese, B. Acc. Chem. Res. 2000, 33, 631.
55. (e) Schuster, G. B. Acc. Chem. Res. 2000, 33, 253.
56. (f) Lewis, F. D.; Lestinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159.
57. (g) Giese, B. Annu. Rev. Biochem. 2002, 71, 51.
58. (a) Steenken, S. Chem. Rev. 1989, 89, 503.
59. (b) Steenken, S. Biol. Chem. 1997, 378, 1293.
60. (c) Li, X.; Cai, Z.; Sevilla, M. D. J. Phys. Chem. B 2001, 105, 10115.
61. (d) Weatherly, S. C.; Yang, I. V.; Thorp, H. H. J. Am. Chem. Soc. 2001, 123, 1236.
62. Reynisson, J.; Steenken, S. Phys. Chem. Chem. Phys. 2002, 4, 5346.
63. (a) Douhal, A.; Kim, S. K.; Zewail, A. H. Nature 1995, 378, 260.
64. (b) Zewail, A. H. J. Phys. Chem. 1996, 100, 12701.
65. Ryu, E. K.; MacCoss, M. J. Org. Chem. 1981, 46, 2819.
66. Lipkin, D.; Howard, F. B.; Nowotny, D.; Sano, M. J. Biol. Chem. 1963, 238, 2249.
67. (a) Holmes, R. E.; Robins, R. K. J. Am. Chem. Soc. 1964, 86, 1242.
68. (b) Lin, T. S.; Cheng, J.C.; Ishiguro, K.; Sartorelli, A. C. J. Med. Chem. 1985, 28, 1194.
69. Saneyoshi, M. Chem. Pharm. Bull. 1968, 16, 1616.
70. Yamauchi, K.; Tabnabe, T.; Kinoshita, M. J. Org. Chem. 1979, 44, 638.
71. Sako, M.; Kawada, H.; Hirota, K. J. Org. Chem. 1999, 64, 5719.
72. (a) Buxton, G. V.; Mulazzani, Q. G. In Electron Transfer in Chemistry: Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 538.
73. (b) Spinks, J. W. T.; Woods, R. J. An Introduction to Radiation Chemistry, 3rd ed.; Wiley: New York, 1990; p 100.
74. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
75. Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
76. Zhao, Y.; Pu, J.; Lynch, B. J.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2004, 6, 673.
77. Frisch, M. J., et al. Gaussia 03, revision B.5; Gaussian, Inc.; Pittsburgh, PA, 2003.
78. Zhao, Y.; Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 2715.
79. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908.
80. (a) Guerra, M. Chem. Phys. Lett. 1990, 167, 315.
81. (b) Guerra, M. J. Phys. Chem. A 1999, 103, 5983.
82. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
83. Chatgilialoglu, C.; Gimisis, T.; Guerra, M.; Ferreri, C.; Emanuel, C. J.; Horner, J. H.; Newcomb, M.; Lucarini, M.; Pedulli, G. F. Tetrahedron Lett. 1998, 39, 3947.
84. Guerra, M. Phys. Chem. Chem. Phys. 2001, 3, 3792.
85. Guerra, M. Res. Chem. Intermed. 2002, 28, 257.