β-Haloethanol substrates as probes for radical mechanisms for galactose oxidase

Journal of the American Chemical Society

Volumn 119, Issue 33, 1997, Pages 7743-7749

  Wachter, Rebekka M ^a   Montague Smith, Michael P ^a   Branchaud, Bruce P ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSE OXIDASE; HALOALCOHOL;

ARTICLE; CATALYSIS; ENZYME KINETICS; ENZYME MECHANISM; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0030986450     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626695     Document Type: Article

References (31)

1. Ögel, Z. B.; Brayford, D.; McPherson, M. J. Mycol. Res. 1994, 98, 474-480.
2. Ito, N.; Phillips, S. E. V.; Yadav, K. D. S.; Knowles, P. F. J. Mol. Biol. 1994, 238, 794-814.
3. (a) Kosman, D. J. In Copper Proteins and Copper Enzymes; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 2, pp 1-26.
4. (b) Hamilton, G. A. In Copper Proteins. Metals Ions in Biology; Spiro, T. G., Ed.; John Wiley & Sons: New York, 1981; Vol. 3, pp 193-218.
5. (c) Ettinger, M. J.; Kosman, D. J. in Copper Proteins. Metals Ions in Biology; Spiro, T. G., Ed.; John Wiley & Sons: New York, 1981; Vol. 3, pp 219-261.
6. (a) Ito, N.; Phillips, S. E.; Stevens, C.; Ögel, Z. B.; McPherson, M. J.; Keen, J. N.; Yadav, K. D. S.; Knowles, P. F. Nature 1991, 350, 87-90.
7. Whittaker, M. M.; Whittaker, J. W. J. Biol Chem. 1990, 265, 9610-9613.
8. Babcock, G. T.; El-Deeb, M. K.; Sandusky, P. O.; Whittaker, M. M.; Whittaker, J. W. J. Am. Chem. Soc. 1992, 114, 3727-3734.
9. Whittaker, M. W.; Whittaker, J. W. J. Biol. Chem. 1988, 263, 6074-6080.
10. Branchaud, B. P.; Montague-Smith, M. P.; Kosman, D. J.; McLaren, F. R. J. Am. Chem. Soc. 1993, 115, 798-800.
11. Whittaker, M. M.; Whittaker, J. W. Biophys. J. 1993, 64, 762-772.
12. Wachter, R. M.; Branchaud, B. P. J. Am. Chem. Soc. 1996, 118, 2782-2789.
13. Maradufu, A.; Cree, G. M.; Perlin, A. S. Can. J. Chem. 1971, 49, 3429-3437.
14. (a) Tanner, D. D.; Chen, J. J.; Chen, L.; Luelo, C. J. Am. Chem. Soc. 1991, 113, 8074-8081.
15. See also: (b) Tanner, D. D.; Yang, C. M. J. Org. Chem. 1993, 58, 5907-5914.
16. (c) Tanner, D. D.; Xie, G.-J.; Hooz, J.; Yang, C.-M. J. Org. Chem. 1993, 58, 7138-7142.
17. Montague-Smith, M. P.; Wachter, R. M.; Branchaud, B. P. Anal. Biochem. 1992, 207, 353-355.
18. Tressel, P.; Kosman, D. Biochem. Biophys. Res. Commun. 1980, 92, 781-786.
19. Kitz, R.; Wilson, I. B. J. Biol. Chem. 1962, 237, 3245-3249.
20. (a) Walsh, C. Horizons Biochem. Biophys. 1977, 3, 36-81.
21. (b) Walsh, C. Tetrahedron 1982, 38, 871-909.
22. (c) Silverman, R. B. Methods Enzymol. 1995, 249, 240-283.
23. Kosman, D. J. In Copper Proteins and Copper Enzymes; Lontie, R., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 2, pp 1-26.
24. Ettinger, M. J.; Kosman, D. J. In Copper Proteins. Metals Ions in Biology; Spiro, T. G., Ed.; John Wiley & Sons: New York, 1981; Vol. 3, pp 219-261.
25. This experiment has been used previously to establish that the catalytically inactive form of GOase is one-electron-reduced: Hamilton, G. A.; Adolf, P. K.; deJersey, J.; DuBois, G. C.; Dyrkacz, G. R.; Libby, R. D. J. Am. Chem. Soc. 1978, 100, 1899-1912.
26. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row Harper Collins Publishers: New York, 1987; pp 591-608, especially table on p 592.
27. (a) Saunders, W. H. Acc. Chem. Res. 1976, 9, 19-25.
28. (b) Saunders, W. H., Jr.; Cockerill, A. F. Mechanism of Elimination Reactions; Wiley-Interscience: New York, NY, 1973; Chapter 2.
29. Gandler, J. R.; Yokoyama, T. J. Am. Chem. Soc. 1984, 106, 130-135.
30. Hamilton, G. A.; Adolf, P. K.; deJersey, J.; DuBois, G. C.; Dyrkacz, G. R.; Libby, R. D. J. Am. Chem. Soc. 1978, 100, 1899-1912.
31. O'Reilly, J. E. Biochim. Biophys. Acta 1973, 292, 509-515.