Use of free energy relationships to probe the individual steps of hydroxylation of p-hydroxybenzoate hydroxylase: Studies with a series of 8- substituted flavins

Biochemistry

Volumn 38, Issue 25, 1999, Pages 8124-8137

  Ortiz Maldonado, Mariliz ^a   Ballou, David P ^a   Massey, Vincent ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOATE 3 MONOOXYGENASE; FLAVINE ADENINE NUCLEOTIDE;

ARTICLE; CHEMICAL REACTION; DEHYDRATION; HYDROXYLATION; OXYGEN TRANSPORT; PRIORITY JOURNAL; PROTEIN INTERACTION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

4-HYDROXYBENZOATE-3-MONOOXYGENASE; FLAVIN-ADENINE DINUCLEOTIDE; FLAVINS; HYDROXYLATION; KINETICS; OXIDATION-REDUCTION; PSEUDOMONAS AERUGINOSA; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; THERMODYNAMICS;

EID: 0033594867     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi990560e     Document Type: Article

References (70)

1. Entsch, B., Ballou, D. P., and Massey, V. (1976) J. Biol. Chem. 251, 2250-2263.
2. Entsch, B., Massey, V., and Ballou, D. P. (1974) Biochem. Biophys. Res. Commun. 57, 1018-1025.
3. Massey, V. (1994) J. Biol. Chem. 269, 22459-22462.
4. Anderson, R. F., Patel, K. B., and Stratford, M. R. L. (1987) J. Biol. Chem. 262, 17475-17479.
5. Anderson, R. F., Patel, K. B., and Vojnovic, B. (1991) J. Biol. Chem. 266, 13086-13090.
6. Hamilton, G. A. (1971) Prog. Bioorg. Chem. 1, 83-157.
7. Exner, O. (1988) Correlation Analysis of Chemical Data, Plenum Press, New York.
8. Carey, F. A., and Sundberg, R. J. (1990) Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd ed., pp 179-215, Plenum Press, New York.
9. Hansch, C., and Leo, A. (1995) Exploring QSAR: Fundamentals and Applications in Chemistry and Biology (ACS Professional Reference Book) American Chemical Society, Washington, DC.
10. Hansch, C., and Leo, A. (1995) Exploring QSAR: Hydrophobic, Electronic, and Steric Constants (ACS Professional Reference Book) American Chemical Society, Washington, DC.
11. Hillas, P. J., and Fitzpatrick, P. (1996) Biochemistry 35, 6969-6975.
12. Edmondson, D. E. (1995) Xenobiotica 25, 735-753.
13. Walker, M. C., and Edmondson, D. E. (1994) Biochemistry 33, 1088-1098.
14. Edmondson, D. E., Bhattacharyya, A. K., and Walker, M. C. (1993) Biochemistry 32, 5196-5202.
15. Husain, M., Edmondson, D. E., and Singer, T. P. (1982) Biochemistry 21, 595-600.
16. Pollegioni, L., Blodig, W., and Ghisla, S. (1997) J. Biol. Chem. 272, 4924-4934.
17. Yorita, K., Janko, K., Aki, K., Ghisla, S., Palfey, B. A., and Massey, V. (1997) Proc. Natl. Acad. Sci. U.S.A. 94, 9590-9595.
18. Eckstein, J. W., Hastings, W., and Ghisla, S. (1993) Biochemistry 32, 404-411.
19. Francisco, W. A., Abu-Soud, H. M., Topgi, R., Baldwin, T. O., and Raushel, F. M. (1996) J. Biol. Chem. 271, 104-110.
20. Miller, S. M., and Klinman, J. P. (1985) Biochemistry 24, 2114-2127.
21. Detmer, K., and Massey, V. (1985) J. Biol. Chem. 260, 5998-6005.
22. Blake, R. C., II, and Coon, M. J. (1980) J. Biol. Chem. 255, 4100-4111.
23. Blake, R. C., II, and Coon, M. J. (1981) J. Biol. Chem. 256, 5755-5763.
24. Blake, R. C., II, and Coon, M. J. (1981) J. Biol. Chem. 256, 12127-12133.
25. Blake, R. C., II, and Coon, M. J. (1989) J. Biol. Chem. 264, 3694-3701.
26. Schopfer, L. M., Wessiak, A., and Massey, V. (1991) J. Biol. Chem. 266, 13080-13085.
27. Schopfer, L. M., Massey, V., and Claiborne, A. (1981) J. Biol. Chem. 256, 7329-7337.
28. Lah, M. S., Palfey, B. A., Schreuder, H. A., and Ludwig, M. L. (1994) Biochemistry 33, 1555-1564.
29. Raibekas, A. A., and Jorns, M. S. (1994) Biochemistry 33, 12649-12655.
30. Spencer, R., Fisher, J., and Walsh, C. (1976) Biochemistry 15, 1043-1053.
31. Bull, C., and Ballou, D. P. (1981) J. Biol. Chem. 256, 12673-12680.
32. Hunt, J., and Massey, V. (1992) J. Biol. Chem. 267, 21479-21485.
33. Palfey, B. A., Entsch, B., Ballou, D. P., and Massey, V. (1994) Biochemistry 33, 1545-1554.
34. Entsch, B., Palfey, B. A., Ballou, D. P., and Massey, V. (1991) J. Biol. Chem. 266, 17341-17349.
35. Moran, G. R., and Entsch, B. (1995) Protein Expression Purif. 6, 164-168.
36. Müller, F., and van Berkel, W. J. H. (1982) Eur. J. Biochem. 128, 21-27.
37. Müller, F., Voordouw, G., van Berkel, W. J. H., Steennis, P. J., Visser, S., and van Rooijen, P. J. (1979) Eur. J. Biochem. 101, 235-244.
38. Müller, F. (1991) in Chemistry and Biochemistry of Flavoenzymes (Müller, F., Ed.) p 5, CRC Press, Boca Raton, FL, and Ann Arbor, MI.
39. Murthy, Y. V., and Massey, V. (1998) J. Biol. Chem. 273, 8975-8982.
40. Massey, V. (1990) in Flavins and Flavoproteins (Curti, B., Ronchi, S., and Zanetti, G., Eds.) pp 59-66, Walter de Gruyter and Co., Berlin.
41. Minnaert, K. (1965) Biochim. Biophys. Acta 110, 42-56.
42. Palfey, B. A., Ballou, D. P., and Massey, V. (1997) Biochemistry 36, 15713-15723.
43. Husain, M., and Massey, V. (1979) J. Biol. Chem. 254, 6657-6666.
44. Entsch, B., and Ballou, D. P. (1989) Biochim. Biophys. Acta 999, 313-322.
45. Bevington, P. R. (1969) Data Reduction and Error Analysis for the Physical Sciences, pp 235-242, McGraw-Hill, Inc., New York.
46. Bruice, T. C. (1983) J. Chem. Soc., Chem. Commun., 14.
47. Bruice, T. C., Noar, J. B., Ball, S. S., and Venkataram, U. V. (1983) J. Am. Chem. Soc. 105, 2452-2463.
48. Bruice, T. C. (1981) in Flavins and Flavoproteins (Massey, V., and Williams, C. H., Jr., Eds.) pp 265-277, Elsevier/North-Holland, Inc., New York.
49. Bruice, T. C. (1984) in Flavins and Flavoproteins (Bray, R. C., Engel, P., and Mayhew, S. G., Eds.) pp 45-55, Walter de Gruyter, Berlin.
50. Fox, J. P., and Jencks, W. P. (1974) J. Am. Chem. Soc. 96, 1436-1449.
51. Hine, J. (1975) Structural Effects on Equilibria in Organic Chemistry, Chapter 3, John Wiley and Sons, New York.
52. Charton, M. (1964) J. Org. Chem. 29, 1222-1227.
53. Ballinger, P., and Long, F. A. (1960) J. Am. Chem. Soc. 82, 795-798.
54. Gatti, D. L., Palfey, B. A., Lah, M. S., Entsch, B., Massey, V., Ballou, D. P., and Ludwig, M. L. (1994) Science 266, 110-114.
55. Schreuder, H. A., Mattevi, A., Obmolova, G., Kalk, K. H., Hol, W. G. J., van der Bolt, F. J. T., and van Berkel, W. J. H. (1994) Biochemistry 33, 10161-10170.
56. Moran, G. R., Entsch, B., Palfey, B. A., and Ballou, D. P. (1996) Biochemistry 35, 9278-9285.
57. van der Bolt, F. J. T., Vervoort, J., and van Berkel, W. J. H. (1996) Eur. J. Biochem. 237, 592-600.
58. Ghisla, S., and Massey, V. (1986) Biochem. J. 239, 1-12.
59. Ghisla, S., and Massey, V. (1989) Eur. J. Biochem. 181, 1-17.
60. Maeda-Yorita, K., and Massey, V. (1993) J. Biol. Chem. 268, 4134-4144.
61. Bell, R. P. (1958) The Proton in Chemistry, 2nd ed., pp 68-70, Chapman and Hall, London.
62. Wessiak, A., Schopfer, L. M., and Massey, V. (1984) J. Biol. Chem. 259, 12547-12556.
63. Perrin, D. D. (1965) Dissociation Constants of Organic Bases in Aqueous Solution, Butterworth and Co., London, U.K.
64. Vervoort, J., Van Berkel, W. J., Muller, F., and Moonen, C. T. (1991) Eur. J. Biochem. 200, 731-738.
65. Carey, F. A., and Sundberg, R. J. (1990) Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd ed., pp 539-557, Plenum Press, New York.
66. Vervoort, J., Rietjens, I. M. C. M., van Berkel, W. J. H., and Veeger, C. (1992) Eur. J. Biochem. 206, 479-484.
67. van der Bolt, F. J. T., van der Heuvel, R. H. H., Vervoort, J., and van Berkel, W. J. H. (1997) Biochemistry 36, 14192-14201.
68. Eberlein, G., and Bruice, T. C. (1983) J. Am. Chem. Soc. 105, 6685-6697.
69. Bruice, T. C. (1984) Isr. J. Chem. 24, 54-61.
70. Fee, J. A., and Valentine, J. S. (1977) in Superoxide and Superoxide Dismutases (Michelson, A. M., McCord, J. M., and Fridovich, I., Eds.) pp 25-29, Academic Press, New York.