Antibody-metalloporphyrin catalytic assembly mimics natural oxidation enzymes

Journal of the American Chemical Society

Volumn 121, Issue 39, 1999, Pages 8978-8982

  Nimri, Shai ^a   Keinan, Ehud ^a,b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; METALLOPORPHYRIN; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY SN37 4; PORPHYRIN DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOMER; ENZYME KINETICS; ENZYME LINKED IMMUNOSORBENT ASSAY; ENZYME SUBSTRATE; MICHAELIS MENTEN KINETICS; OXIDATION;

EID: 0032829736     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990314q     Document Type: Article

References (50)

1. (a) Walsh, C.; Latham, J. J. Protein Chem. 1986, 5, 79.
2. (b) Holland, H. L. Chem. Rev. 1988, 88, 473.
3. (c) Jakoby, W. B.; Ziegler, D. M. J. Biol. Chem. 1990, 265, 20715.
4. (a) The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. VII, Chapter 6.
5. (b) Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986.
6. (c) Watanabe, Y.; Oae, S.; Iyanagi, T. Bull. Chem. Soc. Jpn. 1982, 55, 188.
7. (a) Ozaki, S.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056.
8. (b) Ozaki, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 1996, 118, 9784.
9. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
10. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
11. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
12. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
13. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
14. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
15. A few examples: (a) McMurry, T. J.; Groves, J. T. In ref 2b; Chapter 1. (b) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Hiroo, T.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Meunier, B. Chem. Rev. 1992, 92, 1411. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404. (f) Gross, Z.; Nimri, S. J. Am. Chem. Soc. 1995, 117, 8021. (g) Gross, Z.; Ini, S. J. Org. Chem. 1997, 62, 5514.
16. (a) Schultz, P. G.; Lerner, R. A. Science 1995, 269, 1835.
17. (b) Jacobsen, J. R.; Schultz, P. G. Curr. Opin. Struct. Biol. 1995, 5, 818.
18. (c) MacBeath, G.; Hilvert, D. Chem., Biol. 1996, 3, 433.
19. (d) Keinan, E.; Lerner, R. A. Isr. J. Chem. 1996, 36, 113.
20. (e) Thomas, N. R. Nat. Prod. Rep. 1996, 479.
21. Schwabacher, A. W.; Weinhouse, M. I.; Auditor M.-T. M.; Lerner, R. A. J. Am. Chem. Soc. 1989, 111, 2344.
22. Cochran, A. G.; Schultz, P. G. Science 1990, 249, 781.
23. Cochran, A. G.; Schultz, P. G. J. Am. Chem. Soc. 1990, 112, 9414.
24. Harada, A.; Fukushima, H.; Shiotzuki, K.; Yamaguchi, H.; Oka, F.; Kamachi, M. Inorg. Chem. 1997, 36, 6099.
25. (a) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A.; Benory, E.; Ghozi, M. C.; Eshhar, Z.; Green, B. S. Pure Appl. Chem, 1990, 62, 2013.
26. (b) Keinan, E.; Benory, E.; Sinha, S. C.; Sinha-Bagchi, A.; Eren, D.; Eshhar, Z.; Green, B. S. Inorg. Chem. 1992, 31, 5433.
27. For high-valent metallo-oxo-porphyrins, see: (a) Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884. (b) Groves, J. T.; Quinn, R. Inorg. Chem. 1984, 23, 3846-3853. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1987, 109, 3812.
28. For high-valent metallo-oxo-porphyrins, see: (a) Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884. (b) Groves, J. T.; Quinn, R. Inorg. Chem. 1984, 23, 3846-3853. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1987, 109, 3812.
29. For high-valent metallo-oxo-porphyrins, see: (a) Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884. (b) Groves, J. T.; Quinn, R. Inorg. Chem. 1984, 23, 3846-3853. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1987, 109, 3812.
30. For postulated transition states, see: (a) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786. (b) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 6243. (c) Groves, J. T.; Han, Y.; Engen, D. V. J. Chem. Soc., Chem. Commun. 1990, 436-437. (d) Reference 2c.
31. For postulated transition states, see: (a) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786. (b) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 6243. (c) Groves, J. T.; Han, Y.; Engen, D. V. J. Chem. Soc., Chem. Commun. 1990, 436-437. (d) Reference 2c.
32. For postulated transition states, see: (a) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786. (b) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 6243. (c) Groves, J. T.; Han, Y.; Engen, D. V. J. Chem. Soc., Chem. Commun. 1990, 436-437. (d) Reference 2c.
33. For postulated transition states, see: (a) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786. (b) Groves, J. T.; Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 6243. (c) Groves, J. T.; Han, Y.; Engen, D. V. J. Chem. Soc., Chem. Commun. 1990, 436-437. (d) Reference 2c.
34. Buchler, J. W. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. I, Chapter 10.
35. Staros, J. V.; Wright, R. W.; Swingle, D. M. Anal. Biochem. 1986, 156, 220.
36. Goding, J. W. Monoclonal Antibodies: Principles and Practice, 2nd ed.; Academic Press: New York, 1986.
37. Clark, B.; Eengvali, E. In ELISA: Theoretical and Practical Aspects in Enzyme-Immunuassay; Mggio, E. T., Ed.; CRC Press: Boca Raton, FL, 1980; Chapter 8.
38. For example, we examined two other metalloporphyrins, tcpp-Fe-Cl and tcpp-Mn-Cl, that yielded lower ee values (maximum of 10% and 4%, respectively, in the sulfoxidation of thioanisole, S1).
39. assembly is the velocity of the reaction that was catalyzed within the assembly's active site.
40. observed).
41. (c) The catalytic assembly's concentration was considered as 75% of the metalloporphyrin used.
42. + values were adopted from: (a) Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley-Interscience: New York, 1972; pp 145-155. (b) Advances in Linear Free Energy Relationships; Chapman, N., Shorter, J., Eds.; Plenum Press: New York, 1972; pp 455-484.
43. + values were adopted from: (a) Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley-Interscience: New York, 1972; pp 145- 155. (b) Advances in Linear Free Energy Relationships; Chapman, N., Shorter, J., Eds.; Plenum Press: New York, 1972; pp 455-484.
44. + values (ρ = -1.5); i.e., in the absence of porphyrin, a concerted nucleophilic attack of the sulfide on PhIO takes place.
45. Ono, N.; Miyake, H.; Saito, T.; Kaji, A. Synthesis 1980, 952.
46. Saltzman, H.; Sharefkin, G. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 658.
47. Longo, F. R.; Finarelly, M. G.; Kim, J. B. J. Heterocycl. Chem. 1969, 6, 927.
48. Datta-Gupta, N.; Bardos, T. J. J. Heterocycl. Chem. 1966, 3, 495.
49. Le Maux, P.; Bahri, H.; Simonneaux, G. Tetrahedron 1993, 49, 1401.
50. In agreement with: Hartmann, M.; Robert, A.; Durate, V.; Keppler, B. K.; Meunier, B. J. Biol. Inorg. Chem. 1997, 2, 427.