Synthetic heme chemistry: The cradle of functional molecules and catalysts

Chemtracts

Volumn 12, Issue 4, 1999, Pages 229-263

  Collman, James P ^a   Wang, Zhong ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME C OXIDASE; HEME; PORPHYRIN;

CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; MOLECULAR MODEL; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032877033     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (93)

1. (a) Dolphin, D., ed. The Porphyrins, vols, 1-7, Academic Press: New York, 1978/1979
2. (b) Chapman, S.K., Daff, S., Munro, A.W. Struct. Bonding 1997, 88, 39.
3. Jameson, G.B., Ibers, J.A. Biological and synthetic dioxygen carriers. In Bioinorganic Chemistry, Bertini, I., Gray, H.B., Lippard, S.J., Valentine, J.S., eds., University Science Books: Mill Valley, 1994, p. 253.
4. Morre, G.R. Hemoproteins. In Protein Electron Transfer, Bendall, D.S., ed., Bios Scientific Publishers: Oxford, 1996, p. 189.
5. Malatesta, F., Antonini, G., Sarti, P., Brunori, M. Biophys. Chem. 1995, 54, 1.
6. Ortiz de Montellano, P.R. Cytochrome P450, 2nd ed., Plenum: New York, 1995.
7. (a) Jensen, L.H. Methods Enzymol. 1997, 277, 353
8. (b) Betz, M. Biol. Chem. 1997, 378, 167
9. (c) Poulos, T.L. Methods Enzymol. 1996, 272, 358.
10. (a) Wagner, G. Nature Struct. Biol. 1997, 4, 841
11. (b) Palma, P.N., Moura, I., Legall, J., Vanbeeumen, J., Wampler, J.E., Moura, J.J.G. Biochem. J. 1994, 33, 6394
12. (c) Wuthrich, K. Acta Crystallogr. D-Biol. Crystallogr. 1995, 51, 249.
13. (a) Yates, J.R. Method Enzymol. 1996, 271, 351
14. (b) Loo, J.A. Mass Spectrom. Rev. 1997, 16, 1
15. (c) Zaluzee, E.J., Gage, D.A., Watson, J.T. Prot. Express. Purif. 1995, 6, 109.
16. Rector, K.D., Fayer, M.D. Int. Rev. Phys. Chem. 1998, 17, 261.
17. (a) Cammack, R. Cooper C.E. Methods Enzymol. 1993, 227, 353
18. (b) Michel, H., Behr, J., Harrenga, A., Kannt, A. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 329.
19. Smith, K.M. Synthesis of and preparation of porphyrin compounds. In Porphyrins and Metalloporphyrins, Smith, K.M., ed., Elsevier Scientific: New York, 1975, p. 29.
20. Gottwald, L.K., Ullmann, E.F. Tetrahedron Lett. 1969, 3071.
21. Collman, J.P., Gagne, R.R., Reed, C.A., Halbert, T.R., Lang, G., Robinson, W.T. J. Am. Chem. Soc. 1975, 97, 1427.
22. (a) Momenteau, M., Mispelter, J., Loock, B., Bisagni, E. J. Chem. Soc. Perkin Trans. I 1983, 189
23. (b) Staeubli, B., Fretz, H., Piantini, U., Woggon, W.D. Helv. Chem. Acta. 1987, 1173.
24. Tsuchida, E., Hasegawa, E., Komatsu, T., Nakata, T. Bull. Chem. Soc. Jpn. 1991, 888.
25. Bhyrappa, P., Young, J.K., Moore, J.S., Suslick, K.S. J. Am. Chem. Soc. 1996, 118, 5708.
26. Lerner, D.A., Quintal, M.B., Maillard, P., Giannotti, C. J. Chem. Soc. Perkin Trans. II 1990, 1105.
27. (a) Momenteau, M., Mispelter, J., Loock, B., Lhoste, J.M. J. Chem. Soc. Perkin Trans. I 1985, 61
28. (b) Momenteau, M., Loock, B., Huel, C., Lhoste, J.M. J. Chem. Soc. Perkin Trans. I 1988, 283.
29. Benson, D.R., Valentekovich, R., Knobler, C.B., Diederich, F. Tetrahedron 1991, 47, 2401.
30. Collman, J.P., Lee, V.J., Kellen-Yuen, C.J., Zhang, X., Ibers, J.A., Brauman, J.I. J. Am. Chem. Soc. 1995, 117, 692.
31. Lindsey, J.S., Mauzeral, D.C., J. Am. Chem. Soc. 1982, 104, 4498.
32. (a) Collman, J.P., Gagne, R.R., Haibert, T.R., Marchon, J.C., Reed, C.A. J. Am. Chem. Soc. 1973, 95, 7868
33. (b) Collman, J.P., Gagne, R.R., Reed, C.A. J. Am. Chem. Soc. 1974, 96, 2629
34. (c) Collman, J.P., Gagne, R.R., Reed, C.A., Robinson, W.T., Rodley, G.A. Proc. Natl. Acad. Sci. USA 1974, 71, 1326
35. (d) Collman, J.P., Gagne, R.R., Gray, H.B., Hare, J.W. J. Am. Chem. Soc. 1974, 96, 6522
36. (e) Collman, J.P., Gagne, R.R., Kouba, J., Ljusberg-Wahren, H. J. Am. Chem. Soc. 1974, 96, 6800.
37. (a) Collman, J.P., Brauman, J.I., Halbert, T.R., Suslick, K.S. Proc. Natl. Acad. Sci. USA 1976, 73, 3333
38. (b) Collman, J.P., Brauman, J.I., Doxsee, K.M. Proc. Natl. Acad. Sci. USA 1979, 76, 6035
39. (c) Collman, J.P. Acc. Chem. Res. 1977, 10, 265.
40. (a) Groves, J.T., Myers, R.S. J. Am. Chem. Soc. 1983, 105, 5791
41. (b) Maux, P.L., Bahri, H., Simonneaus, G. J. Chem. Soc. Chem. Commun. 1991, 1350
42. (c) Imai, H., Nakagavva, S., Kyuno, E. J. Am. Chem. Soc. 1992, 114, 6719.
43. 2 binding site, presumably providing hydrogen bond to the oxy-heme group. In cytochrome c oxidase, three imidazoles from histidine residues form a copper-chelating site. Phenol groups from tyrosine residues are also found in hemoglobin and mammalian cytochrome c oxidases. (a) Collman, J.P. Inorg. Chem. 1997, 36, 5145 (b) Iwata, S., Ostermeier, C., Ludwig, B., Michel, H. Nature 1995, 376, 660 (c) Tsukihara, T., Aoyama, H., Yamashita, E., Tomizaki, T., Yamaguchi, H., Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yoshikawa, S. Science 1996, 272, 1136 (d) Yoshikawa, S. Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yamashita, E., Inoue, N., Yao, M., Fei, M.J., Libeu, C.P., Mizushima, T., Yamaguchi, H., Tomizaki, T., Tsukihara, T. Science 1998, 280, 1723 (e) Gennis, R.B. Science 1998, 280, 1712.
44. 2 binding site, presumably providing hydrogen bond to the oxy-heme group. In cytochrome c oxidase, three imidazoles from histidine residues form a copper-chelating site. Phenol groups from tyrosine residues are also found in hemoglobin and mammalian cytochrome c oxidases. (a) Collman, J.P. Inorg. Chem. 1997, 36, 5145 (b) Iwata, S., Ostermeier, C., Ludwig, B., Michel, H. Nature 1995, 376, 660 (c) Tsukihara, T., Aoyama, H., Yamashita, E., Tomizaki, T., Yamaguchi, H., Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yoshikawa, S. Science 1996, 272, 1136 (d) Yoshikawa, S. Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yamashita, E., Inoue, N., Yao, M., Fei, M.J., Libeu, C.P., Mizushima, T., Yamaguchi, H., Tomizaki, T., Tsukihara, T. Science 1998, 280, 1723 (e) Gennis, R.B. Science 1998, 280, 1712.
45. 2 binding site, presumably providing hydrogen bond to the oxy-heme group. In cytochrome c oxidase, three imidazoles from histidine residues form a copper-chelating site. Phenol groups from tyrosine residues are also found in hemoglobin and mammalian cytochrome c oxidases. (a) Collman, J.P. Inorg. Chem. 1997, 36, 5145 (b) Iwata, S., Ostermeier, C., Ludwig, B., Michel, H. Nature 1995, 376, 660 (c) Tsukihara, T., Aoyama, H., Yamashita, E., Tomizaki, T., Yamaguchi, H., Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yoshikawa, S. Science 1996, 272, 1136 (d) Yoshikawa, S. Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yamashita, E., Inoue, N., Yao, M., Fei, M.J., Libeu, C.P., Mizushima, T., Yamaguchi, H., Tomizaki, T., Tsukihara, T. Science 1998, 280, 1723 (e) Gennis, R.B. Science 1998, 280, 1712.
46. 2 binding site, presumably providing hydrogen bond to the oxy-heme group. In cytochrome c oxidase, three imidazoles from histidine residues form a copper-chelating site. Phenol groups from tyrosine residues are also found in hemoglobin and mammalian cytochrome c oxidases. (a) Collman, J.P. Inorg. Chem. 1997, 36, 5145 (b) Iwata, S., Ostermeier, C., Ludwig, B., Michel, H. Nature 1995, 376, 660 (c) Tsukihara, T., Aoyama, H., Yamashita, E., Tomizaki, T., Yamaguchi, H., Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yoshikawa, S. Science 1996, 272, 1136 (d) Yoshikawa, S. Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yamashita, E., Inoue, N., Yao, M., Fei, M.J., Libeu, C.P., Mizushima, T., Yamaguchi, H., Tomizaki, T., Tsukihara, T. Science 1998, 280, 1723 (e) Gennis, R.B. Science 1998, 280, 1712.
47. 2 binding site, presumably providing hydrogen bond to the oxy-heme group. In cytochrome c oxidase, three imidazoles from histidine residues form a copper-chelating site. Phenol groups from tyrosine residues are also found in hemoglobin and mammalian cytochrome c oxidases. (a) Collman, J.P. Inorg. Chem. 1997, 36, 5145 (b) Iwata, S., Ostermeier, C., Ludwig, B., Michel, H. Nature 1995, 376, 660 (c) Tsukihara, T., Aoyama, H., Yamashita, E., Tomizaki, T., Yamaguchi, H., Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yoshikawa, S. Science 1996, 272, 1136 (d) Yoshikawa, S. Shinzawa-Itoh, K., Nakashima, R., Yaono, R., Yamashita, E., Inoue, N., Yao, M., Fei, M.J., Libeu, C.P., Mizushima, T., Yamaguchi, H., Tomizaki, T., Tsukihara, T. Science 1998, 280, 1723 (e) Gennis, R.B. Science 1998, 280, 1712.
48. Collman, J.P., Zhang, X., Hermann, P.C., Uffelman, E.S., Boitrel, B., Straumanis, A., Brauman, J.I. J. Am. Chem. Soc. 1994, 116, 2681.
49. Collman, J.P., Boitrel, B., Fu, L., Galanter, J., Straumanis, A., Rapta, M. J. Org. Chem. 1997, 62, 2308.
50. Collman, J.P., Wang, Z., Straumanis, A. J. Org. Chem. 1998, 63, 2424.
51. Pettigrew, G.W., Moore, G.R. Cytochromes c: Evolutionary, Structural and Physicochemical Aspects. Springer-Verlag: New York, 1990.
52. Groves, J.T., Viski, P. J. Org. Chem. 1990, 55, 3628.
53. (a) Collman, J.P., Brauman, J.I., Fitzgerald, J.P., Hampton, P.D., Naruta, Y., Michida, T. Bull. Chem. Soc. Jpn. 1988, 61, 47
54. (b) Collman, J.P., Zhang, X., Brauman, J.I., Hembre, R.T. J. Am. Chem. Soc. 1990, 112, 5356
55. (c) Collman, J.P., Zhang, X., Lee, V.J., Hembre, R.T., Brauman, J.I. ACS Adv. Chem. Ser. 1992, 230, 153.
56. Lindsey, J. J. Org. Chem. 1980, 45, 5215.
57. (a) Pettigrew, G.W., Moore, G.R. Cytochromes c: Biological Aspects, Springer-Verlag: New York, 1987.
58. (b) Frew, J.E., Jones, P. Structure and functional properties of peroxidases and catalases. In Advances in Inorganic and Bioinorganic Mechanisms, vol. 3, Sykes, A.G., ed., Academic Press: London, 1984, p. 175.
59. Collman, J.P., Bröring, M., Fu, L., Rapta, M., Schwenninger, R., Straumanis, A. J. Org. Chem. 1998, 63, 8082.
60. Collman, J.P., Wang, Z. Unpublished results.
61. Some porphyrins with 3.1-geometry (three pickets oriented a and one picket oriented β) were synthesized from αααα-TAPP by functionalization of three pickets and rotating the remaining one. Collman, J.P., Brauman, J.I., Doxsee, K.M., Halbert, T.R., Bunnenberg, E., Linder, R.E., LaMar, G.N., Del Gaudio, J., Lang, G. Spartalian, K. J. Am. Chem. Soc. 1980, 102, 4182.
62. Stark, O., Garben, O. Chem. Ber. 1913, 46, 644.
63. (a) Mezo, G., Mihala, N., Koczan, G., Hudecz, F. Tetrahedron 1998, 54, 6757
64. (b) Patek, M. N.J. Peptide Protein Res. 1993, 42, 97.
65. Greene, T.W., Wuts, P.G.M. eds., Protective Groups in Organic Synthesis, 2nd ed., John Wiley: New York, 1991.
66. Collman, J.P., Bröring, M., Fu, L., Rapta, M., Schwenninger, R. J. Org. Chem. 1998, 63, 8084.
67. (a) Momenteau, M., Reed, C.A. Chem. Rev. 1994, 94, 659
68. (b) Traylor, T.G. Acc. Chem. Res. 1981, 14, 102
69. (c) Reed, C.A. Metal Ions Biol. Systems 1977, 7, 277.
70. Collman, J.P., Brauman, J.I., Iverson, B.L., Sessler, L. Biomin. Chem. Tokyo 1983, 37.
71. Collman, J.P., Herrman, P.C., Fu, L., Eberspacher, T.A., Eubankds, M., Boitrel, B., Hayoz, P., Zhang, X., Brauman, J.I. J. Am. Chem. Soc. 1997, 119, 3481.
72. Collman, J.P., Fu, L., Zingg, A., Diederich, F. Chem. Commun. 1997, 193.
73. Collman, J.P., Herrman, P.C., Boitrel, B., Zhang, X., Eberspacher, T.A., Fu, L. J. Am. Chem. Soc. 1994, 116, 9783.
74. Collman, J.P., Fu, L., Herrmann, P.C., Wang, Z., Rapta, M., Bröring, M., Schwenninger, R., Boitrel, B. Angew. Chem. Int. Ed. Engl. 1998, 37, 3397.
75. Collman, J.P., Fu, L., Herrmann, P.C., Zhang, X. Science 1997, 275, 949.
76. Collman, J.P., Rapta, M., Bröring, M., Raptova, L., Schwenninger, R., Boitrel, B., Fu, L., L'Her, M. J. Am. Chem. Soc. 1999, 121, 1387.
77. Meunier, B. Chem. Rev. 1992, 92, 1411.
78. (a) Urano, Y., Higuchi, T., Hirobe, M., Nagano, T. J. Am. Chem. Soc. 1997, 119, 12008
79. (b) Higuchi, T., Shimada, K., Maruyama, N., Hirobe, M. J. Am. Chem. Soc. 1993, 115, 7551.
80. (a) Volz, H., Holzbecher, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 1442
81. (b) Wagenknecht, H.A., Woggon, W.D. Angew. Chem. Int. Ed. Engl. 1997, 36, 390.
82. (a) Metz, G., Sjostrand, T. Acta Physiol. Scand. 1954, 31, 334
83. (b) Coburn, R.F. Ann. N. Y. Acad. Sci. 1970, 174, 11.
84. Ferguson-Miller, S., Babcock, G.T. Chem. Rev. 1996, 96, 2889.
85. Wikström, M. Nature 1977, 266, 271.
86. Ojima, I. Catalytica Asymmetric Synthesis, VCH: New York, 1993.
87. Canter, M.J., Tarner, P. Coord. Chem. Rev. 1991, 108, 115.
88. Collman, J.P., Zhang, X., Lee, V.J., Uffelman, E.S., Brauman, J.I. Science 1993, 261, 1404.
89. Campbell, L.A., Kodadek, T. J. Mol. Catal. A: Chem. 1996, 113, 293.
90. Collman, J.P., Wang, Z., Straumanis, A., Quelquejeu, M., Rose, E. J. Am. Chem. Soc. 1999, 121, 460.
91. Collman, J.P., Wang, Z., Straumanis, A., Quelquejeu, M., Rose, E. Unpublished results.
92. Naruta, Y., Tani, T., Maruyama, K. Tetrahedron Lett. 1992, 33, 6323.
93. Katsuki, T. J. Mol. Catal. A: Chem. 1996, 113, 87.