Studies on the mechanism of ribonucleotide reductases

Journal of the American Chemical Society

Volumn 119, Issue 12, 1997, Pages 2784-2794

  Lenz, Roman ^a   Giese, Bernd ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

RIBONUCLEOTIDE REDUCTASE;

ARTICLE; ENZYME KINETICS; ENZYME MECHANISM; PH;

EID: 0030891240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962974q     Document Type: Article

References (102)

1. (a) Thelander, L.; Reichard, P. Annu. Rev. Biochem. 1979, 48, 133-158.
2. (b) Eriksson, S.; Sjöberg, B. M. In Allosteric Enzymes; Hervé, G., Ed.; CRC Press: Boca Raton, 1990; pp 189-215.
3. (c) Stubbe, J. Adv. Enzymol. Relat. Areas Mol. Biol. 1990, 63, 349-417.
4. (d) Thelander, L.; Gräslund, A. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker, Inc.: New York, 1994; pp 109-129.
5. (a) Cory, J. G.; Chiba, P. In Inhibitors of Ribonucleotide Diphosphate Reductase Activity; Cory, J. G., Cory, A. H., Eds.; CRC Press: Boca Raton, FL, 1989; pp 245-264.
6. (b) Robins, M. J.; Samano, M. C.; Samano, V. Nucleotides Nucleosides 1995, 14, 485-493.
7. Reichard, P. Science 1993, 260, 1773-1777.
8. (a) Ashley, G. W.; Stubbe, J. Pharmac. Ther. 1985, 30, 301-329.
9. (b) Stubbe, J; van der Donk, W. A. Chem. Biol. 1995, 2, 793-801.
10. (a) Stubbe, J. Molec. Cell. Biochem. 1983, 50, 25-45.
11. (b) Ashley, G. W.; Harris, G.; Stubbe, J. J. Biol. Chem. 1986, 261, 3958-3964.
12. (a) Thelander, L.; Larsson, A.; Hobbs, J.; Eckstein, F. J. Biol. Chem. 1976, 251, 1398-1405.
13. (b) Harris, G.; Ator, M. A.; Stubbe, J. Biochemistry 1984, 23, 5214-5225.
14. (c) Ator, M. A.; Stubbe, J. Biochemistry 1985, 24, 7214-7221.
15. (d) Salowe, S. P.; Ator, M. A.; Stubbe, J. Biochemistry 1987, 26, 3408-3416.
16. (e) Samano, V.; Robins, M. J. J. Org. Chem. 1991, 56, 7108-7113.
17. (a) Mao, S. S.; Johnston, M. I.; Bollinger, J. M.; Stubbe, J. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 1485-1490.
18. (b) Mao, S. S.; Holler, T. P.; Yu, G. X.; Bollinger, J. M.; Booker, S.; Johnston, M. I.; Stubbe, J. Biochemistry 1992, 31, 9733-9743.
19. (c) Mao, S. S.; Holler, T. P.; Bollinger, J. M.; Yu, G. X.; Johnston, M. I.; Stubbe, J. Biochemistry 1992, 31, 9744-9751.
20. (d) Mao, S. S.; Yu, G. X.; Chalfoun, D.; Stubbe, J. Biochemistry 1992, 31, 9752-9759.
21. Auguste, S. P.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1995, 395-404.
22. Samano, V.; Robins, M. J. J. Am. Chem. Soc. 1992, 114, 4007-4008.
23. 11
24. van der Donk, W. A.; Yu, G.; Silva, D. J.; Stubbe, J.; McCarthy, J. R.; Jarvi, E. T.; Matthews, D. P.; Reswick, R. J.; Wagner, E. Biochemistry 1996, 35, 8381-8391.
25. Steenken, S.; Davies, M. J.; Gilbert, B. C. J. Chem. Soc., Perkin Trans. 2 1986, 1003-1010 and references cited therein.
26. von Sonntag, C.; Dizdaroglu, M. Carbohydr. Res. 1977, 58, 21-30.
27. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987; pp 116-166.
28. For a recent overview of methods for the preparation of selenol ester, see: Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 6, pp 461-468.
29. For examples of the use of acyl selenides in radical chemistry, see references cited in Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566-3570.
30. -1 at 25 °C, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323.
31. Ogilvie, K. K.; Beaucage, S. L.; Schifman, A. L.; Theriault, N. Y.; Sadana, K. L. Can. J. Chem. 1978, 56, 2768-2780.
32. For the preparation of the Dess-Martin reagent, see: (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
33. For the preparation of the Dess-Martin reagent, see: (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
34. (a) Samano, V.; Robins, M. J. J. Org. Chem. 1990, 55, 410-412.
35. (b) Samano, V.; Robins, M. J. J. Org. Chem. 1990, 55, 5186-5188.
36. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamija, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
37. Bender, S. L.; Moffett, K. K. J. Org. Chem. 1992, 57, 1646-1647.
38. (a) Huss, S.; De las Heras, F. G.; Camarasa, M. J. Tetrahedron 1991, 47, 1727-1736.
39. (b) Jung, P. M. J.; Burger, A.; Bielmann, J.-F. Tetrahedron Lett. 1995, 36, 1031-1034.
40. For addition reactions of alkylcerium reagents to easily enolizable ketones, see: Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233-4236.
41. TMSC1/TMSimidazole/N,O-bisTMSacetamide (2:3:3), commercially available: Fluka Product No. 85432. See: Chambaz, E. M.; Horning, E. C. Anal. Biochem. 1969, 30, 7-24.
42. Pappas, J. J.; Keaveney, W. P.; Gancher, E.; Berger, M. Tetrahedron Lett. 1966, 4273-4278.
43. Abiko, A.; Roberts, J. C.; Takemasa, T.; Masamune, S. Tetrahedron Lett. 1986, 27, 4537-4540.
44. Ottenheijm, H. C. J.; DeMan J. H. M. Synthesis 1975, 163-164.
45. Devos, A.; Remion, J.; Frisque-Hesbain, A.-M.; Colens, A.; Ghosez, L. J. Chem. Soc., Chem. Commun. 1979, 1180-1181.
46. Gais, H.-J. Angew. Chem. 1977, 89, 251-252.
47. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
48. Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295-299.
49. (a) Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981-3984.
50. (b) Collington, E. W.; Finch, H.; Smith, I. J. Tetrahedron 1985, 26, 681-684.
51. (a) White, J. D.; Amedio, J. C., Jr.; Gut, S.; Jayasinghe, L. J. Org. Chem. 1989, 54, 4268-4271.
52. (b) Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177-1180.
53. Corey, E. J.; Ponder, J. W.; Ulrich, P. Tetrahedron Lett. 1980, 21, 137-140.
54. (a) Schmidt, O. Th. In Methods in Carbohydrate Chemistry; Whistler, R. L., Wolfrom, M. L., Eds.; Academic Press Inc.: New York, 1963; Vol. 2, pp 318-325.
55. (b) de Belder, A. N. Adv. Carbohydr. Chem. 1965, 20, 219-302.
56. Lipshutz, B. H.; Barton, J. C. J. Org. Chem. 1988, 53, 4495-4499.
57. Lal, B.; Gidwani, R. M.; Rupp, R. H. Synthesis 1989, 711-713.
58. (a) Weber, H.; Khorana, H. G. J. Mol. Biol. 1972, 72, 219-249.
59. (b) Zhdanov, R. I.; Zhenodarova, S. Synthesis 1975, 222-245.
60. Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285-3294.
61. Leblanc, Y.; Fitzsimmons, B. J.; Adams, J; Perez, F.; Rokash, J. J. Org. Chem. 1986, 51, 789-793.
62. (a) Sugiyama, H.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1995, 117, 2945-2946.
63. (b) Hansske, F.; Madej, D.; Robins, M. J. Tetrahedron 1984, 40, 125-135.
64. (c) Binkley, R. W.; Hehemann, D. G.; Binkley, W. W. J. Org. Chem. 1978, 43, 2573-2576.
65. Schreiber, S. L.; Ikemoto, N. Tetrahedron Lett. 1988, 29, 3211-3214.
66. Ator, M. A.; Stubbe, J. J. Biol. Chem. 1986, 261, 3595-3599.
67. Matsushige, T.; Koltzenburg, G.; Schulte-Frohlinde, D. Ber. Bunsenges. Phys. Chem. 1975, 79, 657-661.
68. Burchill, C. E.; Perron, K, M. Can. J. Chem. 1971, 49, 2382-2389.
69. (a) Light, J.; Breslow, R. Tetrahedron Lett. 1990, 31, 2957-2958.
70. 48
71. The boiling point of the tin bromide is not given correctly in this reference. In order to purify this compound, we applied Kugelrohr destillation at 240-250 °C and 0.05 mbar.
72. In addition, the irratiation time could be reduced from over 2 h (Table 1, entry 1-3) to less than 5 min (entry 4).
73. This assumption is further supported by the fact that the combined yield of 6 and 32 (as judged by HPLC) exceeded 80% in every kinetic experiment.
74. Tronche, Ch.; Martinez, F. N.; Horner, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845-5848.
75. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739-7742.
76. For an analogous explanation using thiols as H-donors see ref 51.
77. Beckwith, A. L. J.; Glover, S. A. Aust. J. Chem. 1987, 40, 157-173.
78. Johnson, C. C.; Horner, J. H.; Tronche, Ch.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684-1687.
79. Dhanabalasingham, B.; Martinez, F. N.; Simakov, P. A.; Newcomb, M. Unpublished results.
80. -1 for the H-atom transfer from the tin hydride 35 to a secondary α,β-dimethoxyalkyl radical in acetonitrile/water (1:1) at 34 °C.
81. (a) Jencks, W. P. Chem. Rev. 1972, 72, 705-718.
82. (b) Jencks, W. P. Acc. Chem. Res. 1976, 9, 425-432.
83. (c) Hoffmann, R. W. Aufklärung von Reaktionsmechanismen; Thieme Verlag: Stuttgart, 1976; pp 231-243.
84. General base catalysis has also been observed in the radical-induced dehydration reaction of carbohydrates, see: (a) Tamba, M.; Quintiliani, M. Radiat. Phys. Chem. 1984, 23, 259-263. (b) Akhlaq, M. S.; Al-Baghdadi, S.; von Sonntag, C. Carbohydr. Res. 1987, 16, 71-83.
85. General base catalysis has also been observed in the radical-induced dehydration reaction of carbohydrates, see: (a) Tamba, M.; Quintiliani, M. Radiat. Phys. Chem. 1984, 23, 259-263. (b) Akhlaq, M. S.; Al-Baghdadi, S.; von Sonntag, C. Carbohydr. Res. 1987, 16, 71-83.
86. (a) Bansal, K. M.; Grätzel, M.; Henglein, A.; Janata, E. J. Phys. Chem. 1973, 77, 16-19.
87. (b) Steenken, S. J. Phys. Chem. 1979, 83, 595-599.
88. Hayon, E.; Simic, M. Acc. Chem. Res. 1974, 7, 114-121.
89. +) ≈ -2), the presence of the carbon-centered radical in 25 therefore increases the aciditiy of the α-hydroxy group by more than 7 orders of magnitude, while the basicity of the β-hydroxy group is only enhanced by 3-4 orders of magnitude.
90. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1-19.
91. Uhlin, U.; Eklund, H. Nature 1994, 370, 533-539.
92. (a) Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
93. (b) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984, pp 229-269.
94. Page, M. I. Chem. Soc. Rev. 1973, 2, 295-323.
95. Akhlaq, M. S.; Schuchmann, H.-P.; von Sonntag, C. Int. J. Radiat. Biol. 1987, 51, 91-102.
96. Schöneich, C.; Bonifacic, M.; Asmus, K.-D. Free Rad. Res. Commun. 1989, 6, 393-405.
97. Schwarz, H. A., Dodson, R. W. J. Phys. Chem. 1989, 93, 409-414.
98. Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1986, 90, 5915-5917.
99. For the generation of unnatural derivatives, see: (a) Robins, M. J.; Guo, Z.; Samano, M. C.; Wnuk, S. F. J. Am. Chem. Soc. 1996, 118, 11317-11318. (b) Lehmann, T. E.; Berkessel, A. J. Org. Chem. 1997, 62, 302-309.
100. For the generation of unnatural derivatives, see: (a) Robins, M. J.; Guo, Z.; Samano, M. C.; Wnuk, S. F. J. Am. Chem. Soc. 1996, 118, 11317-11318. (b) Lehmann, T. E.; Berkessel, A. J. Org. Chem. 1997, 62, 302-309.
101. Xi, C.; Jun-Dong, Z.; Li-He, Z. Synthesis 1989, 383-384.
102. Newcomb, M. Tetrahedron 1991, 49, 1151-1176.