Reaction profile of the last step in cytochrome P-450 catalysis revealed by studies of model complexes

Journal of Biological Inorganic Chemistry

Volumn 2, Issue 4, 1997, Pages 492-506

  Gross, Zeev ^a   Nimri, Shay ^a   Barzilay, Claudia M ^a   Simkhovich, Liliya ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Compound I; Cytochrome P 450; Heme enzymes; Oxoiron; Porphyrin cation radicals

Indexed keywords

CHLORIDE PEROXIDASE; CYTOCHROME C PEROXIDASE; CYTOCHROME P450; HEMOPROTEIN; PORPHYRIN;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; ENZYME KINETICS; ISOMERISM; PRIORITY JOURNAL; SPECTROSCOPY;

EID: 0030763479     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007750050161     Document Type: Article

References (74)

1. Collman JP, Gagne RR, Reed CA, Halbert TR, Lang G, Robinson WT (1975)J Am Chem Soc 97:1427-1439
2. Morgan B, Dolphin D (1987) Structure and Bonding 64:115-203
3. Ortiz de Montellano PR (ed) (1986) Cytochrome P-450, structure, mechanism, and biochemistry. Plenum, New York London
4. Andersson LA, Dawson JH (1990) Structure and Bonding 74:1-40
5. Mansuy D (1994) Pure Appl Chem 66:737-744
6. Meunier B (1994) In: Montanari F, Casella L (eds) Metalloporphyrins catalyzed oxidations. Kluwer, Dordrecht Boston London, pp 1-47
7. Collman JP, Zhang X, Lee VJ, Uffelman E, Brauman JI (1993) Science 261:1404-1411
8. Groves JT, Han Y (1995) In: Ortiz de Montellano PR (ed) Cytochrome P-450, structure, mechanism, and biochemistry (2nd edn). Plenum, New York London, Chapter 1
9. Egawa T, Shimada H, Ishimura Y (1994) Biochem Biophys Res Commun 201:1464-1469
10. Edwards SL, Xuong N-H, Hamlin RC, Kraut J (1987) Biochemistry 26:1503-1511
11. Schultz CE, Rutter R, Sage JT, Debrunner P, Hager LP (1984) Biochemistry 23:4743-4754
12. Rutter R, Hager LP, Dhonau H, Hendrich M, Valentine M, Debrunner P (1984) Biochemistry 23:6809-6816
13. Trautwein AX, Bill E, Bominaar EL, Winkler H (1991) Structure and Bonding 78:1-95
14. Weiss R, Mandon D, Wolter T, Trautwein AX, Müther M, Bill E, Gold A, Jayaraj K, Terner J (1996) JBIC 1:377-383
15. Watanabe Y, Groves JT (1992) In: Sigman DS (ed) Mechanisms of catalysis. (The enzymes, vol 20) Academic, San Diego London, pp 406-452
16. Groves JT, Haushalter RC, Nakamura M, Nemo TE, Evans BJ (1981) J Am Chem Soc 103:2884-2886
17. Bill E, Ding XQ, Bominaar EL, Trautwein AX, Winkler H, Mandon D, Weiss R, Gold A, Jayaraj K, Hatfield WE, Kirk ML (1990) Eur J Biochem 188:665-672
18. Hashimoto S, Tatsuno Y, Kitagawa T (1987) J Am Chem Soc 109:8096-8097
19. Kincaid JR, Schneider AJ, Paeng KJ (1989) J Am Chem Soc 111:735-737
20. Penner-Hahn JE, McMurry TJ, Renner MW, Latos-Grazynski L, Eble KS, Davis IM, Balch AL, Groves JT, Dawson JH, Hodgson KO (1983) J Biol Chem 258:12 761-12 764
21. Groves JT, McMurry TJ (1985) Rev Port Quim 27:102-103
22. Balch AL, Latos-Grazynski L, Renner MW (1985) J Am Chem Soc 107:2983-2985
23. Gross Z, Nimri S (1994) Inorg Chem 33:1731-1732
24. Poulos TL (1996) JBIC 1:356-359
25. Fulop V, Phizackerley RP, Soltis SM, Clifton IJ, Wakatsuki S, Erman J, Hajdu J, Edwards SL (1994) Structure 2:201-208
26. Penner-Hahn JE, Hodgson KO (1989) In: Lever ABP, Gray HB (eds) Physical bioinorganic chemistry, Series 4, Part III, Iron porphyrins. VCH, Weinheim, pp 235-304
27. Paeng KJ, Kincaid JR (1988) J Am Chem Soc 110:7913-7915
28. Oertling WA, Babcock GT (1988) Biochemistry 27:3331-3338
29. Hashimoto S, Teraoka J, Inubishi T, Yonetani T, Kitagawa T (1986) J Biol Chem 261:11 110-11 118
30. Reczek CM, Sitter AJ, Terner J (1989) J Mol Struct 214:27-41
31. Sitter AJ, Reczek CM, Terner J (1985) J Biol Chem 260:7515-7522
32. Hashimoto S, Mizutani Y, Tatsuno Y, Kitagawa T (1991) J Am Chem Soc 113:6542-6549
33. Groves JT, McClusky GA (1976) J Am Chem Soc 98:859-861
34. Groves JT, Gross Z (1995) In: Kessissoglou DP (ed) Bioinorganic chemistry: an inorganic perspective of life (NATO ASI Series, vol 459). Kluwer, Dordrecht, pp 39-47
35. Groves JT, Avaria-Neisser GE, Fish KM, Imachi M, Kuczkowski RL (1986) J Am Chem Soc 108:3837-3838
36. Collman JP, Brauman JI, Hampton PD, Tanaka H, Bohle DS, Hembre RT (1990) J Am Chem Soc 112:7980
37. Arasasingham RD, He GX, Bruice TC (1993) J Am Chem Soc 115:7985-7991
38. Traylor TG (1991) Pure Appl Chem 63:265-274
39. Rietjens IMCM, Osman AM, Veeger C, Zakharieva O, Antony J, Grodzicki M, Trautwein AX (1996) JBIC 1:372-376
40. Khenkin AM, Hill CL (1993) J Am Chem Soc 115:8178-8186
41. Groves JT, Watanabe Y (1986) J Am Chem Soc 108:507-508
42. Gross Z, Nimri S (1995) J Am Chem Soc 117:8021-8022
43. Czarnecki K, Nimri S, Gross Z, Proniewicz LM, Kincaid JR (1996) J Am Chem Soc 118:2929-2935
44. Gross Z, Nimri S, Simkhovich L (1996) J Mol Cat A: Chem 113:231-238
45. Groves JT, Gross Z, Stern MK (1994) Inorg Chem 33:5065-5072
46. Gans P, Buisson G, Duee E, Marchon J-C, Erler BS, Scholz WF, Reed CA (1986) J Am Chem Soc 108:1223-1234
47. Kaustov L, Tal ME, Shames AI, Gross Z (1997) Inorg Chem 36:in press
48. Sisemore MF, Burstyn JN, Valentine JS (1996) Angew Chem Int Ed Eng 35:206-208, Angew Chem 108:195-196
49. Sisemore MF, Burstyn JN, Valentine JS (1996) Angew Chem Int Ed Eng 35:206-208, Angew Chem 108:195-196
50. Machii K, Watanabe Y, Morishima I (1995) J Am Chem Soc 117:6691-6697
51. Groves JT, Quinn R, McMurry TJ, Nakamura M, Lang G, Boso B (1985) J Am Chem Soc 107:354-360
52. Sugitomo H, Tung H, Sawyer DT (1988) J Am Chem Soc 110:2465-2470
53. Barzilay CM, Sibilia SA, Spiro TG, Gross Z (1995) Chem Eur J 1:222-231
54. Groves JT, Watanabe Y (1986) J Am Chem Soc 108:7836-7837
55. La Mar GN, Walker FA (1979) In: Dolphin D (ed) The porphyrins, vol 4. Academic, New York, pp 61-157
56. Toney GE, terHaar LW, Savrin JE, Gold A, Hatfield WE, Sangaiah R (1984) Inorg Chem 23:2561-2563
57. Reed CA, Guiset F (1996) J Am Chem Soc 118:3281-3282
58. Turner P, Gunter MJ (1994) Inorg Chem 33:1406-15
59. Basolo F, Pearson RG (1962) Prog Inorg Chem 4:381-453
60. Chapman NB, Shorter J (1972) Advances in linear free energy relationships. Plenum, New York
61. Gross Z, Kaustov L (1995) Tetrahedron Lett 36:3735-3736
62. Swistak C, Mu XH, Kadish KM (1987) Inorg Chem 26:4360-4366
63. Ostovic D, Bruice TC (1989) J Am Chem Soc 111:6511-6517
64. Spreer LO, Maliyackel AC, Otros JW, Melvin C (1987) Inorg Chem 26:4133-5
65. Camenzind MJ, Hollander FJ, Hill CL (1982) Inorg Chem 21:4301-4308
66. Hickman DL, Nanthakumar A, Goff HM (1988) J Am Chem Soc 110:6384-6390
67. Watabe T, Akamatsu K (1974) Biochem Pharmacol 23:1079-1085
68. Groves JT, Nemo TE, Myers RS (1979) J Am Chem Soc 101:1032-1033
69. Collman JP, Kodadek T, Raybuck SA, Brauman JI, Papazian LM (1985) J Am Chem Soc 107:4343-4345
70. Gross Z, Ini S (1997) J Org Chem 62 (in press)
71. Palucki M, Pospisil PJ, Zhang W, Jacobsen EN (1994) J Am Chem Soc 116:9333-9334
72. Higuchi T, Hirobe M (1996) J Mol Cat A: Chem 113:403-422
73. Gross Z (1996) JBIC 1:372-376
74. Bernardou J, Fabiano A-S, Robert A, Meunier B (1994) J Am Chem Soc 116:9375-9376