Model studies for heme oxygenase-catalyzed porphyrin meso hydroxylation

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1195-1198

  Zhu, Yaoqiu ^a   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HEME; HEME OXYGENASE; MESOPORPHYRIN;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; OXIDATION REDUCTION REACTION;

CATALYSIS; HEME; HEME OXYGENASE (DECYCLIZING); HYDROXYLATION; MESOPORPHYRINS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 34147116141     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063088f     Document Type: Article

References (29)

1. Abraham, N. G.; Lin, J. H. C.; Schwartzman, M. L.; Levere, R. D.; Shibahara, S. Int. J. Biochem. 1988, 20, 543-558.
2. (a) Davydov, R. M.; Yoshida, T.; Ikeda-Saito, M.; Hoffman, B. M. J. Am. Chem. Soc. 1999, 121, 10656-10657.
3. (b) Liu, Y.; Moënne-Locoz, P.; Loehr, T. M.; Ortiz de Montellano, P. R. J. Biol. Chem. 1997, 272, 6909-6917.
4. (c) Matera, K. M.; Takahashi, S.; Fujii, H.; Zhou, H.; Ishikawa, K.; Yoshimura, T.; Rousseau, D. L.; Yoshida, T.; Ikeda-Saito, M. J. Biol. Chem. 1996, 271, 6618-6624.
5. (d) Yoshida, T.; Noguchi, M.; Kikuchi, G.; Sano, S. J. Biochem. 1981, 90, 125-131.
6. (e) Yoshinaga, T.; Sudo, Y.; Sano, S. Biochem. J. 1990, 270, 659-664.
7. Noguchi, M.; Yoshida, T.; Kikuchi, G. J. Biochem. 1982, 91, 1479-1483.
8. (a) Torpey, J.; Ortiz de Montellano, P. R. J. Biol. Chem. 1996, 271, 26067-26073.
9. (b) Torpey, J.; Ortiz de Montellano, P. R. J. Biol. Chem. 1997, 272, 22008-22014.
10. (a) Bonnett, R.; Stephenson, G. F. J. Org. Chem. 1965, 30, 2791-2798.
11. (b) Bonnett, R.; Gale, I. A. D.; Stephenson, G. F. J. Chem. Soc., C 1966, 1600-1604.
12. (c) Torpey, J. W.; Ortiz de Montellano, P. R. J. Org. Chem. 1995, 60, 2195-2199.
13. (d) Bonnett, R.; Cornell, P.; McDonaglf, A. F. J. Chem. Soc., Perkin Trans. 1976, 794-800.
14. (e) Jackson, A. H.; Rao, K. R. N.; Wilkins, M. J. Chem Soc., Perkin Trans. 1 1987, 307-311.
15. (a) Marletta, M. A. J. Biol. Chem. 1993, 268, 12231-12234.
16. (b) Zhu, Y.; Silverman, R. B. J. Am. Chem. Soc. 2005, 127, 858-868.
17. (c) Lee-Robichaud, P.; Shyadehi, A. Z.; Wright, J. N.; Akhtar, M.; Akhtar, M. Biochemistry 1995, 34, 14104-14113.
18. (d) Park, M. J.; Lee, J.; Suh, Y.; Kim, J.; Nam, W. J. Am. Chem. Soc. 2006, 128, 2630-2634.
19. Sugishima, M.; Omata, Y.; Kakuta, Y.; Sakamoto, H.; Noguchi, M.; Fukuyama, K. FEBS Lett. 2000, 471, 61-66.
20. Bonnett, R.; McDonagh, A. F. J. Chem. Soc., Perkin Trans. 1 1973, 881-888.
21. Crusats, J.; Suzuki, A.; Mizutani, T.; Ogoshi, H. J. Org. Chem. 1998, 63, 602-607.
22. Zhu, Y.; Silverman, R. B. J. Org. Chem. 2007, 72, 233-239.
23. Smith, K. M.; Fujinari, E. U.; Langry, K. C.; Parish, D. W.; Tabba, H. D. J. Am. Chem. Soc. 1983, 105, 6638-6646.
24. Zhu, Y.; Nikolic, D.; Van Breemen, R. B.; Silverman, R. B. J. Am. Chem. Soc. 2005, 127, 858-868.
25. (a) Saito, S.; Itano, H. A. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 1393-1397.
26. (b) Jackson, A. H.; Nagaraja Rao, K. R.; Wilkins, M. J. Chem. Soc., Perkin Trans. I 1987, 307-311.
27. (c) Saito, S.; Itano, H. A. J. Chem. Soc., Perkin Trans. I 1987, 1183-1188.
28. (d) Heirwegh, K. P. M.; Blanckaert, N.; Van Hesss, G. Anal. Biochem. 1991, 195, 273-278.
29. Sakamoto, H.; Omata, Y.; Adachi, Y.; Palmer, G.; Noguchi, M. J. Inorg. Biochem. 2000, 82, 113-121.