Synthesis, Structural Characterization, and Extradiol Oxygenation of Iron-Catecholato Complexes with Hydrotris(pyrazolyl)borate Ligands

Inorganic Chemistry

Volumn 37, Issue 11, 1998, Pages 2614-2615

  Ogihara, Tamako ^a   Hikichi, Shiro ^a   Akita, Munetaka ^a   Moro oka, Yoshihiko ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001038368     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9716215     Document Type: Article

References (45)

1. (a) Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607.
2. (b) Que, L., Jr. In Iron Carriers and Iron Proteins; Loehr, T. M., Ed.; VCH: New York, 1989; pp 467-524.
3. (a) Ohlendorf, D. H.; Lipscomb, J. D.; Weber, P. C. Nature 1988, 336, 403.
4. (b) Ohlendorf, D. H.; Orville, A. M.; Lipscomb, J. D. J. Mol. Biol. 1994, 244, 586.
5. (c) Orville, A. M.; Elango, N.; Lipscomb, J. D.; Ohlendorf, D. H. Biochemistry 1997, 36, 10039.
6. (d) Orville, A. M.; Lipscomb, J. D.; Ohlendorf, D. H. Biochemistry 1997, 36, 10052.
7. (a) Han, S.; Eltis, L. D.; Timmis, K. N.; Muchmore, S. W.; Bolin, J. T. Science 1995, 270, 976.
8. (b) Senda, T.; Sugiyama, K.; Narita, H.; Yamamoto, T.; Kimbara, K.; Fukuda, M.; Sato, M.; Yano, K.; Mitsui, Y. J. Mol. Biol. 1996, 255, 735.
9. (a) Bertini, I.; Briganti, F.; Mangani, S.; Nolting, H. F.; Scozzafava, A. Coord. Chem. Rev. 1995, 114, 321.
10. (b) Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759.
11. (c) Shu, L.; Chiou, Y.-M.; Orville, A. M.; Miller, M. A.; Lipscomb, J. D.; Que, L., Jr. Biochemistry 1995, 34, 6649.
12. (a) Que, L., Jr.; Kolanczyk, R. C.; White, L. S. J. Am. Chem. Soc. 1987, 109, 5373.
13. (b) Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1988, 110, 8085.
14. (c) Jang, H. G.; Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1991, 113, 9200.
15. (a) Koch, W. O.; Krüger, H.-J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2671.
16. (b) Duda, M.; Pascaly, M.; Krebs, M. J. Chem. Soc., Chem. Commun. 1997, 835.
17. (a) Weller, M. G.; Weser, U. J. Am. Chem. Soc. 1982, 104, 3752.
18. (b) Weller, M. G.; Weser, U. Inorg. Chim. Acta 1985, 107, 243.
19. (c) Nishida, Y.; Shimo, H.; Kida, S. J. Chem. Soc., Chem. Commun. 1984, 1611.
20. (a) Dei, A.; Gatteschi, D.; Pardi, L. Inorg. Chem. 1993, 32, 1389.
21. (b) Ito, M.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 1342.
22. Kitajima, N.; Tolman, W. B. Prog. Inorg. Chem. 1995, 43, 419 and references therein.
23. (a) Ito, M.; Amagai, H.; Fukui, H.; Kitajima, N.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1996, 69, 1937.
24. (b) Hikichi, S.; Ogihara, T.; Fujisawa, K.; Kitajima, N.; Akita, M.; Moro-oka, Y. Inorg. Chem. 1997, 36, 4539.
25. Synthetic procedures and characterization data (including X-ray work) for all new compounds are provided as Supporting Information.
26. The structure of the DBCH-chelating Fe(II) complex has been reported: Chiou, Y.-M.; Que, L., Jr. Inorg. Chem. 1995, 34, 3577.
27. Cox, D. D.; Benkovic, S. J.; Bloom, L. M.; Bradley, F. C.; Nelson, M. J.; Que, L., Jr.; Wallick, D. E. J. Am. Chem. Soc. 1988, 110, 2026.
28. (a) Buchanan, R. M.; Kessel, S. L.; Downs, H. H.; Pierpont, C. G.; Hendrickson, D. N. J. Am. Chem. Soc. 1978, 100, 7894.
29. (b) Boone, S. R.; Purser, G. H.; Chang, H.-R.; Lowery, M. D.; Hendrickson, D. N.; Pierpont, C. G. J. Am. Chem. Soc. 1989, 111, 2292.
30. (c) Attia, A. S.; Conklin, B. J.; Lange, C. W.; Pierpont, C. G. Inorg. Chem. 1996, 35, 1033.
31. (d) Lauffer, R. B.; Heistand, R. H., II.; Que, L., Jr. Inorg. Chem. 1983, 22, 50.
32. R ligand have been reported: Ruf, M.; Noll, B. C.; Groner, M. D.; Yee, G. T.; Pierpont, C. G. Inorg. Chem. 1997, 36, 4860.
33. 2 to give the Fe(III) catecholato complex 3.
34. The two isoiners of the extradiol products were identified by comparison with the authentic compounds prepared according to ref 22c.
35. In the TACN system, formation of the quinone product is major reaction and only a trace amount of the intradiol product is obtained in the absence of an additional aromatic N donor ligand (refs 8).
36. 2 rt) as follows: for 2, +206 mV; for 3, +100 mV.
37. Funabiki, T.; Tada, S.; Yoshioka, T.; Takano, M.; Yoshida, S. J. Chem. Soc., Chem. Commun. 1986, 1699.
38. Barbaro, P.; Bianchini, C.; Mealli, C.; Meli, A. J. Am. Chem. Soc. 1991, 113, 3181.
39. Although the structures of the intermediates have not been revealed, some examples of catalytic extradiol catechol cleavage by iron, ruthenium, and vanadium compounds have been reported: Fe; (a) Funabiki, T.; Mizoguchi, A.; Sugimoto, T.; Tada, S.; Tsuji, M.; Sakamoto, H. Yoshida, S. J. Am. Chem. Soc. 1986, 108, 2921. (b) Funabiki, T.; Yoneda, I.; Ishikawa, M.; Ujiie, M.; Nagai, Y.; Yoshida, S. J. Chem. Soc., Chem. Commun. 1994, 1453. Ru: Matumoto, M.; Kuroda, K. J. Am. Chem. Soc. 1982, 104, 1433. V.: Tatsuno, Y.; Tatsuda, M.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1982, 1100.
40. Although the structures of the intermediates have not been revealed, some examples of catalytic extradiol catechol cleavage by iron, ruthenium, and vanadium compounds have been reported: Fe; (a) Funabiki, T.; Mizoguchi, A.; Sugimoto, T.; Tada, S.; Tsuji, M.; Sakamoto, H. Yoshida, S. J. Am. Chem. Soc. 1986, 108, 2921. (b) Funabiki, T.; Yoneda, I.; Ishikawa, M.; Ujiie, M.; Nagai, Y.; Yoshida, S. J. Chem. Soc., Chem. Commun. 1994, 1453. Ru: Matumoto, M.; Kuroda, K. J. Am. Chem. Soc. 1982, 104, 1433. V.: Tatsuno, Y.; Tatsuda, M.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1982, 1100.
41. Although the structures of the intermediates have not been revealed, some examples of catalytic extradiol catechol cleavage by iron, ruthenium, and vanadium compounds have been reported: Fe; (a) Funabiki, T.; Mizoguchi, A.; Sugimoto, T.; Tada, S.; Tsuji, M.; Sakamoto, H. Yoshida, S. J. Am. Chem. Soc. 1986, 108, 2921. (b) Funabiki, T.; Yoneda, I.; Ishikawa, M.; Ujiie, M.; Nagai, Y.; Yoshida, S. J. Chem. Soc., Chem. Commun. 1994, 1453. Ru: Matumoto, M.; Kuroda, K. J. Am. Chem. Soc. 1982, 104, 1433. V.: Tatsuno, Y.; Tatsuda, M.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1982, 1100.
42. Although the structures of the intermediates have not been revealed, some examples of catalytic extradiol catechol cleavage by iron, ruthenium, and vanadium compounds have been reported: Fe; (a) Funabiki, T.; Mizoguchi, A.; Sugimoto, T.; Tada, S.; Tsuji, M.; Sakamoto, H. Yoshida, S. J. Am. Chem. Soc. 1986, 108, 2921. (b) Funabiki, T.; Yoneda, I.; Ishikawa, M.; Ujiie, M.; Nagai, Y.; Yoshida, S. J. Chem. Soc., Chem. Commun. 1994, 1453. Ru: Matumoto, M.; Kuroda, K. J. Am. Chem. Soc. 1982, 104, 1433. V.: Tatsuno, Y.; Tatsuda, M.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1982, 1100.
43. Catechol 1,2-dioxygenase, which is the Fe(III) dependent intradiol enzyme, also carries out extradiol cleavage toward some substrate analogues: (a) Fujiwara, M.; Golovleva, L. A.; Saeki, Y.; Nozaki, M.; Hayaishi, O. J. Biol. Chem. 1975, 250, 4848. (b) Hou, C. T.; Patel, R.; Lillard, M. O. Appl. Environ. Microbiol. 1977, 33, 725. Pascal, R. A., Jr.; Huang, D.-S. Arch. Biochem. Biophys. 1986, 248, 130.
44. Catechol 1,2-dioxygenase, which is the Fe(III) dependent intradiol enzyme, also carries out extradiol cleavage toward some substrate analogues: (a) Fujiwara, M.; Golovleva, L. A.; Saeki, Y.; Nozaki, M.; Hayaishi, O. J. Biol. Chem. 1975, 250, 4848. (b) Hou, C. T.; Patel, R.; Lillard, M. O. Appl. Environ. Microbiol. 1977, 33, 725. Pascal, R. A., Jr.; Huang, D.-S. Arch. Biochem. Biophys. 1986, 248, 130.
45. Catechol 1,2-dioxygenase, which is the Fe(III) dependent intradiol enzyme, also carries out extradiol cleavage toward some substrate analogues: (a) Fujiwara, M.; Golovleva, L. A.; Saeki, Y.; Nozaki, M.; Hayaishi, O. J. Biol. Chem. 1975, 250, 4848. (b) Hou, C. T.; Patel, R.; Lillard, M. O. Appl. Environ. Microbiol. 1977, 33, 725. Pascal, R. A., Jr.; Huang, D.-S. Arch. Biochem. Biophys. 1986, 248, 130.