“Picket Fence Porphyrins”. Synthetic Models for Oxygen Binding Hemoproteins

Journal of the American Chemical Society

Volumn 97, Issue 6, 1975, Pages 1427-1439

  Coliman, James P ^a   Gagne, Robert R ^a   Reed, Christopher A ^a   Halbert, Thomas R ^a   Robinson, Ward T ^a   Lang, George ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HEMOPROTEIN; OXYGEN; PORPHYRIN;

ARTICLE; CHEMICAL MODEL; PROTEIN BINDING; SPECTROSCOPY; SYNTHESIS;

HEMEPROTEINS; MODELS, CHEMICAL; OXYGEN; PORPHYRINS; PROTEIN BINDING; SPECTRUM ANALYSIS; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0016856701     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00839a026     Document Type: Article

References (82)

1. J. P. Coliman, R. R. Gagne, T. R. Halbert, J.-C. Marchon, and C. A. Reed, J. Amer. Chem. Soc., 95, 7868 (1973).
2. J. P. Coliman, R. R. Gagne, and C. A. Reed, J. Amer. Chem. Soc., 96, 2629 (1974).
3. J. P. Coliman, R. R. Gagne, H. B. Gray, and J. Hare, J. Amer. Chem. Soc., 96, 6522 (1974).
4. J. P. Coliman, R. R. Gagne, C. A. Reed, W. T. Robinson, and G. A. Rodley, Proc. Nat. Acad. Sci. U. S., 71, 1326 (1974).
5. R. E. Dickerson and I. Geis, “The Structure and Action of Proteins,” Harper and Row, New York, N.Y., 1969.
6. C. L. Nobbs, H. C. Watson, and J. C. Kendrew, Nature (London), 209, 339 (1966).
7. J. C. Kendrew, R. E. Dickerson, B. E. Strandberg, R. G. Hart, D. R. Davies, D. C. Phillips, and V. C. Shore, Nature., 185, 442 (1960).
8. J. C. Kendrew, Sci. Amer., 205, 96 (1961).
9. J. C. Kendrew, H. C. Watson, B. E. Strandberg, R. E. Dickerson, D. C. Phillips, and V. C. Shore, Nature (London), 190, 666 (1961).
10. J. C. Kendrew, Brookhaven Symp. Biol., 15, 216 (1962).
11. H. C. Watson, Progr. Stereochem., 4 (1968).
12. J. L. Hoard, Science, 174, 1295 (1971).
13. J. L. Hoard In “Structural Chemistry and Molecular Biology,” A. Rich and N. Davidson, Ed., W. H. Freeman, San Fancisco, Calif., 1968, p 573.
14. J. L. Hoard, M. J. Hamor, T. A. Hamor, and W. S. Caughey, J. Amer. Chem. Soc., 87, 2312 (1965).
15. M. F. Perutz and L. F. Ten Eyck, Cold Spring Harbor Symp. Quant. Biol., 36, 295 (1972).
16. M. F. Perutz, Nature (London), 226, 726 (1970).
17. H. Muirhead and M. F. Perutz, Nature (London), 199, 633 (1963).
18. M. F. Perutz, M. G. Rossman, A. F. Cullis, H. Muirhead, G. Will, and A. C. T. North, Nature (London), 185, 416 (1960).
19. J. S. Griffith, Proc. Roy. Soc., Ser. A., 235, 23 (1956).
20. L. Pauling, Stanford Med. Bull., 6, 215 (1948).
21. L. Pauling, Nature (London), 203, 182 (1964).
22. J. J. Weiss, Nature (London), 202, 83 (1964).
23. L. Vaska, Science, 140, 809 (1963).
24. J. S. Valentine, Chem. Rev., 73, 235 (1973).
25. V. J. Choy and C. J. O'Connor, Coord. Chem. Rev., 9, 145 (1972).
26. L. Kievan, J. Peone, Jr., and S. K. Madan, J. Chem. Educ., 50, 670 (1973).
27. G. A. Rodley and W. T. Robinson, Nature (London), 235, 438 (1972).
28. G. A. Rodley and W. T. Robinson, Syn. Inorg. Metal-Org. Chem., 3, 387 (1973).
29. J. P. Coliman, H. Takaya, B. Winkler, L. Libit, S. K. Seah, G. A. Rodley, and W. T. Robinson, J. Amer. Chem. Soc., 95, 1656 (1973).
30. L. D. Brown and K. N. Raymond, J. Chem. Soc., Chem. Commun., 470 (1974).
31. M. Calligaris, G. Nardin, L. Randaccio, and G. Tauzher, Inorg. Nucl. Chem. Lett., 9, 419 (1973).
32. B. M. Hoffman, D. L. Diemente, and F. Basolo, J. Amer. Chem. Soc., 92, 61 (1970).
33. D. Diemente, B. M. Hoffman, and F. Basolo, Chem. Commun., 467 (1970).
34. E. Melamud, B. L. Silver, and Z. Dori, J. Amer. Chem. Soc., 96, 4689 (1974).
35. A. H. Corwin and Z. Reyes, J. Amer. Chem. Soc., 78, 2437 (1956).
36. J. H. Wang, J. Amer. Chem. Soc., 80, 3168 (1958).
37. J. F. Drake and R. J. P. Williams, Nature (London), 182, 1084 (1958).
38. W. R. McClellan and R. E. Benson, J. Amer. Chem. Soc., 88, 5165 (1966).
39. J. O. Alben, W. H. Fuchsman, C. A. Beaudreau, and W. S. Caughey, Biochemistry, 7, 624 (1968).
40. D. Vonderschmitt, K. Bernauer, and S. Fallab, Helv. Chim. Acta, 48, 951 (1965).
41. L. Merchant, M. Sharrock, B. M. Hoffman, and E. Munck, Proc. Nat. Acad. Sci. U. S., 69, 2396 (1972).
42. J. E. Baldwin and J. Huff, J. Amer. Chem. Soc., 95, 5757 (1973).
43. L. K. Chang, et al., J. Amer. Chem. Soc., 95, 5810 (1973).
44. D. L. Anderson, C. J. Weschler, and F. Basolo, J. Amer. Chem. Soc., 96, 5599 (1974).
45. J. Almog, J. E. Baldwin, R. L. Dyer, J. Huff, and C. J. Wilkerson, J. Amer. Chem. Soc., 96, 5600 (1974).
46. M. J. Cowan, J. M. F. Drake, and R. J. P. Williams, Discuss. Faraday Soc., 27, 217 (1959).
47. D. R. Eaton, W. R. McClellan, and J. F. Weiher, Inorg. Chem., 7, 2040 (1968).
48. L. M. Epstein, D. K. Straub, and C. Maricondi, inorg. Chem., 6, 1720 (1967).
49. V. L. Goedken, J. Chem. Soc., Chem. Commun., 207 (1972).
50. A. B. Hoffman, D. M. Collins, V. W. Day, E. B. Fleischer, T. S. Srivastava, and J. L. Hoard, J. Amer. Chem. Soc., 94, 3620 (1972).
51. C. Maricondi, W. Swift, and D. K. Straub, J. Amer. Chem. Soc., 91, 5205 (1969).
52. E. B. Fleischer and T. S. Srivastava, J. Amer. Chem. Soc., 91, 2403 (1969).
53. O. H. W. Kao and J. H. Wang, Biochemistry, 4, 342 (1965).
54. G. S. Hammond and C. -H. S. Wu, Advan. Chem. Ser., No. 77, 186 (1968).
55. J. M. Duelos, Bioinorg. Chem., 2, 263 (1973).
56. H. Diekmann, C. K. Chang, and T. G. Traylor, J. Amer. Chem. Soc., 93, 4069 (1971).
57. L. K. Gottwald and E. F. Ullman, Tetrahedron Lett., 3071 (1969).
58. J. P. Coliman and C. A. Reed, J. Amer. Chem. Soc., 95, 2048 (1973).
59. J. L. Hoard and W. R. Scheldt, Proc. Nat. Acad. Sci. U. S., 70, 3919 (1973).
60. J. L. Hoard, Science, 174, 1295 (1971).
61. L. Pauling and C. D. Coryell, Proc. Nat. Acad. Sci. U. S., 22, 210 (1936).
62. G. Lang and W. Marshall, Proc. Phys. Soc., London, 87, 3 (1966).
63. H. Eicher and A. Trautwein, J. Chem. Phys., 50, 2540 (1969).
64. I. C. Gunsalus, J. R. Meeks, J. D. Lipscomb, P. Debrunner, and E. Munck, in “Molecular Mechanisms of Oxygen Activation,” O. Hayaishi, Ed., Academic Press, New York, N.Y., 1974, p 559.
65. A. L. Crumbliss and F. Basolo, J. Amer. Chem. Soc., 92, 55 (1970.
66. C. Floriani and F. Calderazzo, J. Chem. Soc. A, 946 (1969).
67. L. Herzberg and G. Herzberg, Astrophys. J. 105, 353 (1947).
68. H. Siebert, “Schwingungs Spektroskopie in der Anorganischen Chemie,” Springer-Verlag, Berlin, 1966, pp 40, 51.
69. J. C. Evans, Chem. Commun., 682 (1969).
70. C. H. Barlow, J. C. Maxwell, W. J. Wallace, and W. S. Caughey, Biochem. Biophys. Res. Commun., 55, 91 (1973).
71. J. H. Wang, Accounts Chem. Res., 3, 90 (1970).
72. H. C. Stynes and J. Ibers, J. Amer. Chem. Soc., 94, 5125 (1972).
73. H. Morimoto, H. Lehmann, and M. F. Perutz, Nature (London), 232, 408 (1971).
74. M. F. Perutz and H. Lehmann, Nature (London), 219 (1968).
75. J. H. Wang, A. Nakahara, and E. B. Fleischer, J. Amer. Chem. Soc., 80, 1109 (1958).
76. J. O. Alben and W. S. Caughey, Biochemistry, 7, 175 (1968).
77. V. Ullrich, Angew. Chem., Int. Ed. Engl., 11, 701 (1972).
78. A. Earnshaw, “Introduction to Magnetochemistry,” Academic Press, New York, N.Y., 1968, p. 6.
79. P. Fournari, P. de Cointent, and E. Laviron, Bull. Soc. Chim. Fr., 6, 2438 (1968).
80. P. Fournari, P. de Cointent, and E. Laviron, Chem. Abstr., 68, 59583Z (1968).
81. L. R. Ocone and B. P. Block, Inorg. Syn., 125 (1966).
82. C. W. Lard and R. C. Horn, Anal. Chem., 32, 878 (1960).