Catalytic oxidation of alkenes with a surface-bound metalloporphyrin- peptide conjugate

Tetrahedron

Volumn 55, Issue 7, 1999, Pages 1859-1870

  Geier III, G Richard ^a   Sasaki, Tomikazu ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Biomimetic reactions; Catalysis; Epoxidation; Porphyrins

Indexed keywords

ALKENE DERIVATIVE; METALLOPORPHYRIN; PEPTIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; EPOXIDATION; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

EID: 0033548009     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01227-7     Document Type: Article

References (65)

1. (a) Sheldon, R. A., Ed., Metalloporphyrins in Catalytic Oxidations; Marcel Dekker, Inc.: New York, 1994.
2. (b) Montanari, F, and Casella, L., Eds., Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Boston, 1994.
3. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; and Brauman, J. I. Science 1993, 261, 1410.
4. (d) Montanari, F.; Banfi, S.; Pozzi, G.; and Quici, S. Rev. Heteroatom Chem. 1992, 6, 94.
5. (e) Meunier, B. Chem. Rev. 1992, 92, 1411.
6. (f) Gunter, M. J.; and Turner, P. Coord. Chem. Rev. 1991, 108, 115.
7. (g) White, P. W. Bioorg. Chem. 1991, 18, 440.
8. Ortiz de Montellano, P. R., Ed., Cytochrome P-450: Structure, Mechanism, and Biochemistry, 2nd Edition; Plenum Press: New York, 1995.
9. Groves, J. T.; Nemo, T. E.; and Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032.
10. (a) Takagi, S.; Takahashi, E.; Miyamoto, T. K.; and Sasaki, Y. Chem. Lett. 1986, 1275.
11. (b) Traylor, P. S.; Dolphin, D.; and Traylor, T. G. J. Chem. Soc. Chem. Commun. 1984, 279.
12. (a) Naruta, Y. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Marcel Dekker, Inc.: New York, 1994, 241-260.
13. (b) Boschi, T.; Licoccia, S.; Paolesse, R.; and Tagliatesta, P. In Metalloporphyrins Catalyzed Oxidations; Montanari, F.; and Casella, L., Eds.; Kluwer Academic Publishers: Boston, 1994, 239-268.
14. (c) Naruta, Y.; Ishihara, N.; Tani, F.; and Maruyama, K. Bull. Chem. Soc. Jpn. 1993, 66, 158.
15. (d) Naruta, Y.; Ishihara, N.; Tani, F.; and Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865.
16. (a) Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J. A.; and Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692.
17. (b) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; and Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834.
18. Geier, G. R.; and Sasaki, T. Tetrahedron Lett. 1997, 38, 3821.
19. Geier, G. R. The Preparation of a Metalloporphyrin-Peptide Conjugate Artificial Protein for the Catalytic Oxidation of Alkenes. University of Washington, 1997.
20. Geier, G. R.; Lybrand, T. P.; and Sasaki, T. Tetrahedron 1999, 55, 1871.
21. (a) Naruta, Y.; Tani, F.; and Maruyama, K. Tetrahedron Lett. 1992, 33, 6323.
22. (b) Tatsuno, Y.; Sekiya, A.; Tani, K.; and Saito, T. Chem. Lett. 1986, 889.
23. Loach, P. A.; and Calvin, M. Biochemistry 1963, 2, 361.
24. (a) Jones, R. D.; Summerville, D. A.; and Basolo, F. J. Am. Chem. Soc. 1978, 100, 4416.
25. (b) Boucher, L. J. Coord. Chem. Rev. 1972, 7, 289.
26. (c) Adler, A. D.; Longo, F. R.; Kampas, and F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443.
27. (d) Boucher, L. J. J. Am. Chem. Soc. 1968, 90, 6640.
28. (e) Rothemund, P.; and Menotti, A. R. J. Am. Chem. Soc. 1948, 70,1808.
29. (a) Luo, P.; and Baldwin, R. L. Biochemistry 1997, 36, 8413.
30. (b) Chen, Y. H.; Yang, J. T.; and Chau, K. H. Biochemistry 1974, 13, 3350.
31. Groves, J. T.; and Stern, M. K. J. Am. Chem. Soc. 1987, 109, 3812.
32. (a) Gross, Z.; and Ini, S. J. Org. Chem. 1997, 62, 5514.
33. (b) Arasasingham, R. D.; He, G. X.; and Bruice, T. C. J. Am. Chem. Soc. 1993, 115, 7985.
34. (c) Groves, J. T.; and Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628.
35. (a) Anelli, P. L.; Banfi, S.; Legramandi, F.; Montanari, F.; Pozzi, G.; and Quici, S. J. Chem. Soc. Perkin Trans. 1 1993, 1345.
36. (b) Montanari, F.; Penso, M.; Quici, S.; and Vigano, P. J. Org. Chem. 1985, 50, 4888.
37. (c) Renaud, J. P.; Battioni, P.; Bartoli, J. F.; and Mansuy D. J. Chem. Soc. Chem. Commun. 1985, 888.
38. (d) Meunier, B.; Guilmet, E.; De Carvalho, M. E.; and Poilblanc, R. J. Am. Chem. Soc. 1984, 106, 6668.
39. (e) Razenberg, J. A. S. J.; Nolte, R. J. M.; and Drenth, W. Tetrahedron Lett. 1984, 25, 789.
40. (f) Collman, J. P.; Kodadek, T.; Raybuck, S. A.; and Meunier, B. Proc. Natl. Acad. Sci.; USA 1983, 80, 7039.
41. (g) van der Made, A. W.; Smeets, J. W. H.; Nolte, R. J. M.; and Drenth, W. J. Chem. Soc. Chem. Commun. 1983, 1364.
42. (h) Guilmet, E.; and Meunier, B. Tetrahedron Lett. 1982, 23, 2449.
43. (i) Guilmet, E.; and Meunier, B. Nouv. J. Chim. 1982, 6, 511.
44. (a) Banfi, S.; Maiocchi, A.; Montanari, F.; and Quici, S, Gazz. Chim. Ital. 1990, 120, 123.
45. (b) Banfi, S.; Maiocchi, A.; Moggi, A.; Montanari, F.; and Quici, S. J Chem. Soc. Chem. Commun. 1990, 1794.
46. (c) Banfi, S.; Montanari, F.; and Quici, S. J. Org. Chem. 1989, 54, 1850.
47. (d) Yuan, L. C.; and Bruice, T. C. J. Am. Chem. Soc. 1986, 108, 1643.
48. (a) Gilmartin, C.; and Lindsay Smith, J. R. J. Chem. Soc. Perkin Trans. 2 1995, 243.
49. (b) Iamamato, Y.; Idemori, Y. M.; and Nakagaki, S. J. Mol. Catal. A: Chem. 1995, 99, 187.
50. (c) Iamamoto, Y.; Ciuffu, K. J.; Sacco, H. C.; Prada, C. M. C.; De Moraes, M.; and Nascimento, O. R. J. Mol. Catal. 1994, 88, 167.
51. (d) Cooke, P. R.; and Lindsay Smith, J. R. J. Chem. Soc. Perkin Trans. 1, 1994, 1913.
52. (e) Lindsay Smith, J. R. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Marcel Dekker, Inc.: New York, 1994, 325-368.
53. (f) Cooke, P. R,; and Lindsay Smith, J. R. Tetrahedron Lett. 1992, 33, 2737.
54. (g) Tatsumi, T.; Nakamura, M.; and Tominaga, H. Catal. Today 1989, 6, 163.
55. (h) Tatsumi, T.; Nakamura, M.; and Tominaga, H. Chem. Lett. 1989, 419.
56. Leal, O.; Anderson, D. L; Bowman, R. G.; Basolo, F.; and Burwell, R. L. J. Am. Chem. Soc. 1975, 97, 5125.
57. (a) Collman, J. P.; Zhang, X.; Lee, V. J.; and Brauman, J. I. J. Chem. Soc. Chem. Commun. 1992, 1647.
58. (b) Groves, J. T.; and Viski, P. J. Org. Chem. 1990, 55, 3628.
59. (a) Ostovic, D.; He, G. X.; and Bruice, T. C. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Marcel Dekker, Inc.: New York, 1994, 29-68.
60. (b) Ostovic, D.; and Bruice, T. C. Accs. Chem. Res. 1992, 25, 314.
61. (a) Mansuy, D.; LeClaire, J.; Fontecave, M.; and Momenteau, M. Biochem. Biophys. Res. Commun. 1984, 119, 319.
62. (b) Mansuy, D.; LeClaire, J.; Fontecave, J.; and Dansette, P. Tetrahedron 1984, 40, 2847.
63. Collman, J. P.; Kodadek, T.; and Brauman, J. I. J. Am. Chem. Soc. 1986, 108, 2588.
64. Lucas, H. J.; Kennedy, E. R.; and Formo, M. W. In Organic Syntheses; Wiley: New York, 1955, Vol. 3, 483-485.
65. Christian, G. D. In Analytical Chemistry, 3rd Edition; John Wiley and Sons: New York, 1980, 278-280.