pH-dependent studies reveal an efficient hydroxylation mechanism of the oxygenase component of p-hydroxyphenylacetate 3-hydroxylase

Journal of Biological Chemistry

Volumn 286, Issue 1, 2011, Pages 223-233

  Ruangchan, Nantidaporn ^a   Tongsook, Chanakan ^a   Sucharitakul, Jeerus ^b   Chaiyen, Pimchai ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

COSUBSTRATES; FLAVIN-DEPENDENT; FLOW TECHNIQUES; HIGH PH; HYDROXYLASES; MONOOXYGENASES; OXYGENASES; PH-DEPENDENT; STOPPED FLOW; SUBSTRATE INHIBITION; TWO-COMPONENT; VARIOUS PH;

CATALYSIS; DEHYDRATION; DEWATERING; ENZYME ACTIVITY; ENZYMES; HYDROXYLATION; OXYGEN; OXYGENATION; RATE CONSTANTS; REACTION KINETICS; SUBSTRATES;

PH EFFECTS;

4 HYDROXYPHENYLACETATE 3 HYDROXYLASE; 4 HYDROXYPHENYLACETIC ACID; HYDROGEN PEROXIDE; OXYGEN; OXYGENASE; UNCLASSIFIED DRUG;

ACINETOBACTER BAUMANNII; ARTICLE; BIOACCUMULATION; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ELIMINATION REACTION; ENZYME SUBSTRATE; NONHUMAN; PH; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA;

ACINETOBACTER BAUMANNII; CATALYTIC DOMAIN; ENZYME INHIBITORS; FLAVIN MONONUCLEOTIDE; HYDROGEN-ION CONCENTRATION; HYDROXYLATION; KINETICS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; OXYGEN; PHENYLACETATES; PSEUDOMONAS AERUGINOSA;

EID: 78650947225     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M110.163881     Document Type: Article

References (65)

1. van Berkel, W. J., Kamerbeek, N. M., and Fraaije, M. W. (2006) J. Biotechnol. 124, 670-689
2. Ballou, D. P., Entsch, B., and Cole, L. J. (2005) Biochem. Biophys. Res. Commun. 338, 590-598
3. Palfey, B. A., Ballou, D. P., and Massey, V. (1995) in Active Oxygen: Reactive Oxygen Species in Biochemistry (Valentine, J. S., Foote, C. S., Greenburg, A., and Lieberman, J. F., eds) pp. 37-83, Chapman-Hall, Scotland, UK
4. Torres Pazmiño, D. E., Winkler, M., Glieder, A., and Fraaije, M. W. (2010) J. Biotechnol. 146, 9-24
5. Entsch, B., Cole, L. J., and Ballou, D. P. (2005) Arch. Biochem. Biophys. 433, 297-311
6. Palfey, B. A., and McDonald, C. A. (2010) Arch. Biochem. Biophys. 493, 26-36
7. Gunsalus-Miguel, A., Meighen, E. A., Nicoli, M. Z., Nealson, K. H., and Hastings, J. W. (1972) J. Biol. Chem. 247, 398-404
8. Ellis, H. R. (2010) Arch. Biochem. Biophys. 497, 1-12
9. Chaiyen, P., Suadee, C., and Wilairat, P. (2001) Eur. J. Biochem. 268, 5550-5561
10. Kirchner, U., Westphal, A. H., Müller, R., and van Berkel, W. J. H. (2003) J. Biol. Chem. 278, 47545-47553
11. Webb, B. N., Ballinger, J. W., Kim, E., Belchik, S. M., Lam, K. S., Youn, B., Nissen, M. S., Xun, L., and Kang, C. (2010) J. Biol. Chem. 285, 2014-2027
12. Xun, L., and Webster, C. M. (2004) J. Biol. Chem. 279, 6696-6700
13. Perry, L. L., and Zylstra, G. J. (2007) J. Bacteriol. 189, 7563-7572
14. Otto, K., Hofstetter, K., Röthlisberger, M., Witholt, B., and Schmid, A. (2004) J. Bacteriol. 186, 5292-5302
15. Tischler, D., Eulberg, D., Lakner, S., Kaschabek, S. R., van Berkel, W. J., and Schlömann, M. (2009) J. Bacteriol. 191, 4996-5009
16. van Hellemond, E. W., Janssen, D. B., and Fraaije, M. W. (2007) Appl. Environ. Microbiol. 73, 5832-5839
17. Eichhorn, E., van der Ploeg, J. R., and Leisinger, T. (1999) J. Biol. Chem. 274, 26639-26646
18. Zhan, X., Carpenter, R. A., and Ellis, H. R. (2008) Biochemistry 47, 2221-2230
19. Witschel, M., Nagel, S., and Egli, T. (1997) J. Bacteriol. 179, 6937-6943
20. Valton, J., Fontecave, M., Douki, T., Kendrew, S. G., and Nivière, V. (2006) J. Biol. Chem. 281, 27-35
21. Koskiniemi, H., Metsä-Ketelä, M., Dobritzsch, D., Kallio, P., Korhonen, H., Mäntsälä, P., Schneider, G., and Niemi, J. (2007) J. Mol. Biol. 372, 633-648
22. Lin, S., van Lanen, S. G., and Shen, B. (2008) J. Am. Chem. Soc. 130, 6616-6623
23. Yeh, E., Garneau, S., and Walsh, C. T. (2005) Proc. Natl. Acad. Sci. U.S.A. 102, 3960-3965
24. Dong, C., Flecks, S., Unversucht, S., Haupt, C., van Pée, K. H., and Naismith, J. H. (2005) Science 309, 2216-2219
25. Balibar, C. J., and Walsh, C. T. (2006) Biochemistry 45, 15444-15457
26. Heemstra, J. R., Jr., and Walsh, C. T. (2008) J. Am. Chem. Soc. 130, 14024-14025
27. Neumann, C. S., Walsh, C. T., and Kay, R. R. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 5798-5803
28. Maeda-Yorita, K., and Massey, V. (1993) J. Biol. Chem. 268, 4134-4144
29. Schopfer, L. M., and Massey, V. (1980) J. Biol. Chem. 255, 5355-5363
30. Powlowski, J., Ballou, D., and Massey, V. (1989) J. Biol. Chem. 264, 16008-16016
31. Sheng, D., Ballou, D. P., and Massey, V. (2001) Biochemistry 40, 11156-11167
32. Torres Pazmiño, D. E., Baas, B. J., Janssen, D. B., and Fraaije, M. W. (2008) Biochemistry 47, 4082-4093
33. Chaiyen, P., Brissette, P., Ballou, D. P., and Massey, V. (1997) Biochemistry 36, 8060-8070
34. Chaiyen, P., Brissette, P., Ballou, D. P., and Massey, V. (1997) Biochemistry 36, 13856-13864
35. Suske, W. A., van Berkel, W. J., and Kohler, H. P. (1999) J. Biol. Chem. 274, 33355-33365
36. Crozier-Reabe, K. R., Phillips, R. S., and Moran, G. R. (2008) Biochemistry 47, 12420-12433
37. Suadee, C., Nijvipakul, S., Svasti, J., Entsch, B., Ballou, D. P., and Chaiyen, P. (2007) J. Biochem. 142, 539-552
38. Arunachalam, U., Massey, V., and Miller, S. M. (1994) J. Biol. Chem. 269, 150-155
39. Sucharitakul, J., Chaiyen, P., Entsch, B., and Ballou, D. P. (2006) J. Biol. Chem. 281, 17044-17053
40. Chakraborty, S., Ortiz-Maldonado, M., Entsch, B., and Ballou, D. P. (2010) Biochemistry 49, 372-385
41. Gisi, M. R., and Xun, L. (2003) J. Bacteriol. 185, 2786-2792
42. Kantz, A., Chin, F., Nallamothu, N., Nguyen, T., and Gassner, G. T. (2005) Arch. Biochem. Biophys. 442, 102-116
43. Yeh, E., Cole, L. J., Barr, E. W., Bollinger, J. M., Jr., Ballou, D. P., and Walsh, C. T. (2006) Biochemistry 45, 7904-7912
44. Valton, J., Mathevon, C., Fontecave, M., Nivière, V., and Ballou, D. P. (2008) J. Biol. Chem. 283, 10287-10296
45. Bruice, T. C. (1984) Isr. J. Chem. 24, 54-61
46. Venkataram, U. V., and Bruice, T. C. (1984) J. Chem. Soc. Chem. Commun. 14, 899-900
47. Palfey, B. A., and Massey, V. (1998) in Comprehensive Biological Catalysis (Sinnott, M., ed) Vol. 3, pp. 83-154, Academic Press, San Diego
48. Ortiz-Maldonado, M., Ballou, D. P., and Massey, V. (1999) Biochemistry 38, 8124-8137
49. Chaiyen, P., Sucharitakul, J., Svasti, J., Entsch, B., Massey, V., and Ballou, D. P. (2004) Biochemistry 43, 3933-3943
50. Chaiyen, P. (2010) Arch. Biochem. Biophys. 493, 62-70
51. Ortiz-Maldonado, M., Entsch, B., and Ballou, D. P. (2004) Biochemistry 43, 15246-15257
52. Thotsaporn, K., Sucharitakul, J., Wongratana, J., Suadee, C., and Chaiyen, P. (2004) Biochim. Biophys. Acta 1680, 60-66
53. Alfieri, A., Fersini, F., Ruangchan, N., Prongjit, M., Chaiyen, P., and Mattevi, A. (2007) Proc. Natl. Acad. Sci. U.S.A. 104, 1177-1182
54. Arunachalam, U., Massey, V., and Vaidyanathan, C. S. (1992) J. Biol. Chem. 267, 25848-25855
55. Galán, B., Díaz, E., Prieto, M. A., and García, J. L. (2000) J. Bacteriol. 182, 627-636
56. Okai, M., Kudo, N., Lee, W. C., Kamo, M., Nagata, K., and Tanokura, M. (2006) Biochemistry 45, 5103-5110
57. Kim, S. H., Hisano, T., Takeda, K., Iwasaki, W., Ebihara, A., and Miki, K. (2007) J. Biol. Chem. 282, 33107-33117
58. Sucharitakul, J., Chaiyen, P., Entsch, B., and Ballou, D. P. (2005) Biochemistry 44, 10434-10442
59. Sucharitakul, J., Phongsak, T., Entsch, B., Svasti, J., Chaiyen, P., and Ballou, D. P. (2007) Biochemistry 46, 8611-8623
60. Macheroux, P., Ghisla, S., Sanner, C., Rüterjans, H., and Müller, F. (2005) BMC Biochem. 6, 26
61. Merényi, G., and Lind, J. (1991) J. Am. Chem. Soc. 113, 3146-3153
62. Evans, M. G., and Uri, N. (1949) Trans. Faraday Soc. 45, 224-230
63. Eberlein, G., and Bruice, T. C. (1983) J. Am. Chem. Soc. 105, 6685-6697
64. Entsch, B., Palfey, B. A., Ballou, D. P., and Massey, V. (1991) J. Biol. Chem. 266, 17341-17349
65. Ishimitsu, T., Fujiwara, Y., and Hirose, S. (1979) Talanta 26, 67-69