Copper-promoted overall transformation of 4-tert-butylphenol to its para-hydroxyquinonic derivative, 2-hyroxy-5-tert-butyl-1,4-benzoquinone. Biomimetic studies on the generation of Topaquinone in copper amine oxidases

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 9, 2000, Pages 989-992

  Rinaldi, Andrea C ^a   Ponticelli, Gustavo ^b   Oliva, Stefania ^a   Di Giulio, Antonio ^c   Sanjust, Enrico ^a  

^a Cattedra di Chimica Biologica   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; 4 TERT BUTYLPHENOL; AMINE OXIDASE (COPPER CONTAINING); COPPER;

ARTICLE; BIOGENESIS; CHEMICAL MODIFICATION; ENZYME ACTIVE SITE; ENZYME STRUCTURE; HYDROXYLATION; MOLECULAR MODEL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

AMINE OXIDASE (COPPER-CONTAINING); BENZOQUINONES; COPPER; DIHYDROXYPHENYLALANINE; HYDROGEN-ION CONCENTRATION; HYDROXYLATION; LYSINE; OXIDATION-REDUCTION; PHENOLS; QUINONES;

EID: 0034192496     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00145-1     Document Type: Article

References (25)

1. For a recent review see (a) Hartmann, C.; McIntire, W. S. Methods Enzymol. 1997, 280, 98. Model studies on TPQ and LTQ are reported in
2. (b) Rinaldi, A. C.; Rescigno, A.; Rinaldi, A.; Sanjust, E. Bioorg. Chem. 1999, 27, 253.
3. (c) Suzuki, S.; Yamaguchi, K.; Nakamura, N.; Tagawa, Y.; Kuma, H.; Kawamoto, T. Inorg. Chim. Acta 1998, 283, 260.
4. Janes S.M., Mu D., Wemmer D., Smith A.J., Kaur S., Maltby D., Burlingame A.L., Klinman J.P. Science. 248:1990;981.
5. Tanizawa K. J. Biochem. 118:1995;671.
6. (a) Bono, P.; Salmi, M.; Smith, D. J.; Jalkanen, S. J. Immunol. 1998, 160, 5563.
7. (b) McIntire, W. S. Annu. Rev. Nutr. 1998, 18, 145.
8. Wang S.X., Mure M., Medzihradszky K.F., Burlingame A.L., Brown D.E., Dooley D.M., Smith A.J., Kagan H.M., Klinman J.P. Science. 273:1996;1078.
9. Harrison M.D., Dameron C.T. J. Biochem. Mol. Toxicol. 13:1999;93.
10. Rucker, R. B.; Rucker, B. R.; Mitchell, A. E.; Cui, C. T.; Clegg, M.; Kosonen, T.; Uriu-Adams, J. Y.; Tchaparian, E. H.; Fishman, M.; Keen, C. L. J. Nutr. 1999, 129, 2143.
11. (b) Rucker, R. B.; Cui, C. T.; Tchaparian, E. H.; Mitchell, A. E.; Uriu-Adams, J. Y.; Keen, C. L. Abstracts of Papers, 2nd International Meeting on Copper Homeostasis and its Disorders: Molecular and Cellular Aspects, Ravello, Italy, 17-21 September 1999; p 36.
12. Sayre L.M., Nadkarni D.V. J. Am. Chem. Soc. 116:1994;3157.
13. (a) Rinaldi, A. C.; Porcu, M. C.; Curreli, N.; Rescigno, A.; Finazzi-Agrò, A.; Pedersen, J. Z.; Rinaldi, A.; Sanjust, E. Biochem. Biophys. Res. Commun. 1995, 214, 559.
14. (b) Rinaldi, A. C.; Porcu, C. M.; Oliva, S.; Curreli, N.; Rescigno, A.; Sollai, F.; Rinaldi, A.; Finazzi-Agrò, A.; Sanjust, E. Eur. J. Biochem. 1998, 251, 91.
15. 2O, as reported by Moënne-Loccoz, P.; Nakamura, N.; Steinebach, V.; Duine, J. A.; Mure, M.; Klinman, J. P.; Sanders-Loehr, J. Biochemistry 1995, 34, 7020. The reaction of HtBQ, as derived from 4-tert-butylphenol, with phenylhydrazine is described in the caption of Figure 3.
16. (a) Sanjust, E.; Rinaldi, A. C.; Rescigno, A.; Porcu, M. C.; Alberti, G.; Rinaldi, A.; Finazzi-Agrò, A. Biochem. Biophys. Res. Commun. 1995, 208, 825.
17. (b) Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1995, 117, 8698.
18. Reviewed in Spodine E., Manzur J. Coord. Chem. Rev. 119:1992;171.
19. Urano, Y.; Higuchi, T.; Hirobe, M. Biochem. Biophys. Res. Commun. 1993, 192, 563.
20. (a) Demmin, T. R.; Swerdloff, M. D.; Rogic, M. M. J. Am. Chem. Soc. 1981, 103, 5795.
21. (b) Takizawa, Y.; Munakata, T.; Iwasa, Y.; Suzuki, T.; Mitsuhashi, T. J. Org. Chem. 1985, 50, 4383.
22. Lyons, J. E.; Hsu, C.-Y. In Biological & Inorganic Copper Chemistry; Karlin, K. D.; Zubieta, J., Eds.; Adenine: New York, 1985; pp 57-76.
23. Ruggiero C.E., Smith J.A., Tanizawa K., Dooley D.M. Biochemistry. 36:1997;1953.
24. Su Q., Klinman J.P. Biochemistry. 37:1998;12513.
25. Ruggiero C.E., Dooley D.M. Biochemistry. 38:1999;2892.