Contribution of flavin covalent linkage with histidine 99 to the reaction catalyzed by choline oxidase

Journal of Biological Chemistry

Volumn 284, Issue 25, 2009, Pages 16990-16997

  Quaye, Osbourne ^a   Cowins, Sharonda ^a,b   Gadda, Giovanni ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b ALBANY STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AVERAGE VALUES; C-H BOND CLEAVAGE; CHOLINE OXIDASE; COVALENT LINKAGE; DONOR AND ACCEPTOR; ELECTRON OXIDATION; FLAVIN COFACTOR; GLYCINE BETAINE; HIGH PH; HISTIDINE RESIDUES; LIMITING VALUES; OPTIMAL POSITIONING; PREORGANIZATION; RATE LIMITING; REACTION CATALYZED; TEMPERATURE DEPENDENCE; TUNNELING REACTION; WILD TYPES;

ALDEHYDES; CHEMICAL BONDS;

ENZYMES;

ASPARAGINE; CARBON; CHOLINE OXIDASE; ENZYME VARIANT; FLAVINE ADENINE NUCLEOTIDE; HISTIDINE; HYDROGEN;

ARTICLE; CATALYSIS; CONTROLLED STUDY; COVALENT BOND; ENZYME KINETICS; ENZYME MECHANISM; ENZYME METABOLISM; ENZYME STRUCTURE; NONHUMAN; PH; PRIORITY JOURNAL;

ALCOHOL OXIDOREDUCTASES; AMINO ACID SUBSTITUTION; ARTHROBACTER; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; FLAVIN-ADENINE DINUCLEOTIDE; HISTIDINE; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; RECOMBINANT PROTEINS; THERMODYNAMICS;

EID: 67650541861     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.003715     Document Type: Article

References (70)

1. Malmquist, N. A., Gujjar, R., Rathod, P. K., and Phillips, M. A. (2008) Biochemistry 47, 2466-2475
2. Sygmund, C., Kittl, R., Volc, J., Halada, P., Kubátová, E., Haltrich, D., and Peterbauer, C. K. (2008) J. Biotechnol. 133, 334-342
3. Zamocky, M., Ludwig, R., Peterbauer, C., Hallberg, B. M., Divne, C., Nicholls, P., and Haltrich, D. (2006) Curr. Protein Pept. Sci. 7, 255-280
4. van Berkel, W. J., Kamerbeek, N. M., and Fraaije, M. W. (2006) J. Biotechnol. 124, 670-689
5. Ballou, D. P., Entsch, B., and Cole, L. J. (2005) Biochem. Biophys. Res. Commun. 338, 590-598
6. Ziegler, D. M. (2002) Drug Metab. Rev. 34, 503-511
7. Joosten, V., and van Berkel, W. J. (2007) Curr. Opin. Chem. Biol. 11, 195-202
8. Keller, S., Wage, T., Hohaus, K., Hölzer, M., Eichhorn, E., and van Pée, K. H. (2000) Angew. Chem. Int. Ed Engl. 39, 2300-2302
9. Dong, C., Flecks, S., Unversucht, S., Haupt, C., van Pée, K. H., and Naismith, J. H. (2005) Science 309, 2216-2219
10. Chen, X., and van Pée, K. H. (2008) Acta Biochim. Biophys. Sin. 40, 183-193
11. van Pée, K. H., and Patallo, E. P. (2006) Appl. Microbiol. Biotechnol. 70, 631-641
12. Quaye, O., Lountos, G. T., Fan, F., Orville, A. M., and Gadda, G. (2008) Biochemistry 47, 243-256
13. Wong, C. M., Wong, K. H., and Chen, X. D. (2008) Appl. Microbiol. Biotechnol. 78, 927-938
14. Mewies, M., McIntire, W. S., and Scrutton, N. S. (1998) Protein Sci. 7, 7-20
15. Huang, C. H., Lai, W. L., Lee, M. H., Chen, C. J., Vasella, A., Tsai, Y. C., and Liaw, S. H. (2005) J. Biol. Chem. 280, 38831-38838
16. Lee, M. H., Lai, W. L., Lin, S. F., Hsu, C. S., Liaw, S. H., and Tsai, Y. C. (2005) Appl. Environ. Microbiol. 71, 8881-8887
17. Rand, T., Qvist, K. B., Walter, C. P., and Poulsen, C. H. (2006) FEBS J. 273, 2693-2703
18. Winkler, A., Hartner, F., Kutchan, T. M., Glieder, A., and Macheroux, P. (2006) J. Biol. Chem. 281, 21276-21285
19. Winkler, A., Lyskowski, A., Riedl, S., Puhl, M., Kutchan, T. M., Macheroux, P., and Gruber, K. (2008) Nat. Chem. Biol.
20. Huang, C. H., Winkler, A., Chen, C. L., Lai, W. L., Tsai, Y. C., Macheroux, P., and Liaw, S. H. (2008) J. Biol. Chem. 283, 30990-30996
21. Caldinelli, L., Iametti, S., Barbiroli, A., Fessas, D., Bonomi, F., Piubelli, L., Molla, G., and Pollegioni, L. (2008) Protein Sci. 17, 409-419
22. Caldinelli, L., Iametti, S., Barbiroli, A., Bonomi, F., Fessas, D., Molla, G., Pilone, M. S., and Pollegioni, L. (2005) J. Biol. Chem. 280, 22572-22581
23. Hassan-Abdallah, A., Zhao, G., and Jorns, M. S. (2006) Biochemistry 45, 9454-9462
24. Heuts, D. P., Winter, R. T., Damsma, G. E., Janssen, D. B., and Fraaije, M. W. (2008) Biochem. J. 413, 175-183
25. Winkler, A., Kutchan, T. M., and Macheroux, P. (2007) J. Biol. Chem. 282, 24437-24443
26. Motteran, L., Pilone, M. S., Molla, G., Ghisla, S., and Pollegioni, L. (2001) J. Biol. Chem. 276, 18024-18030
27. Fraaije, M. W., van den Heuvel, R. H., van Berkel, W. J., and Mattevi, A. (1999) J. Biol. Chem. 274, 35514-35520
28. Kim, J., Fuller, J. H., Kuusk, V., Cunane, L., Chen, Z. W., Mathews, F. S., and McIntire, W. S. (1995) J. Biol. Chem. 270, 31202-31209
29. Basran, J., Harris, R. J., Sutcliffe, M. J., and Scrutton, N. S. (2003) J. Biol. Chem. 278, 43973-43982
30. Pang, J., Hay, S., Scrutton, N. S., and Sutcliffe, M. J. (2008) J. Am. Chem. Soc. 130, 7092-7097
31. Kohen, A., Jonsson, T., and Klinman, J. P. (1997) Biochemistry 36, 2603-2611
32. Seymour, S. L., and Klinman, J. P. (2002) Biochemistry 41, 8747-8758
33. Nagel, Z. D., and Klinman, J. P. (2006) Chem. Rev. 106, 3095-3118
34. Fan, F., and Gadda, G. (2005) J. Am. Chem. Soc. 127, 17954-17961
35. Rowland, P., Nielsen, F. S., Jensen, K. F., and Larsen, S. (1997) Structure 5, 239-252
36. Rowland, P., Björnberg, O., Nielsen, F. S., Jensen, K. F., and Larsen, S. (1998) Protein Sci. 7, 1269-1279
37. Fagan, R. L., Nelson, M. N., Pagano, P. M., and Palfey, B. A. (2006) Biochemistry 45, 14926-14932
38. Fan, F., Ghanem, M., and Gadda, G. (2004) Arch. Biochem. Biophys. 421, 149-158
39. Quan, R., Shang, M., Zhang, H., Zhao, Y., and Zhang, J. (2004) Plant Biotechnol. J. 2, 477-486
40. Waditee, R., Bhuiyan, N. H., Hirata, E., Hibino, T., Tanaka, Y., Shikata, M., and Takabe, T. (2007) J. Biol. Chem. 282, 34185-34193
41. Chen, T. H., and Murata, N. (2002) Curr. Opin. plant Biol. 5, 250-257
42. Rontein, D., Basset, G., and Hanson, A. D. (2002) Metab. Eng. 4, 49-56
43. Sánchez-Aguayo, I., Rodríguez-Galán, J. M., García, R., Torreblanca, J., and Pardo, J. M. (2004) Planta 220, 278-285
44. Shirasawa, K., Takabe, T., Takabe, T., and Kishitani, S. (2006) Annals of botany 98, 565-571
45. Waditee, R., Bhuiyan, M. N., Rai, V., Aoki, K., Tanaka, Y., Hibino, T., Suzuki, S., Takano, J., Jagendorf, A. T., Takabe, T., and Takabe, T. (2005) Proc. Natl. Acad. Sci. U. S. A. 102, 1318-1323
46. O'Callaghan, J., and Condon, S. (2000) Int. J. food microbiol. 55, 127-131
47. Peddie, B. A., Chambers, S. T., and Lever, M. (1996) J. Lab. Clin. Med. 128, 417-422
48. Velasco-García, R., Chacón-Aguilar, V. M., Hervert-Hernández, D., and Muñoz-Clares, R. A. (2003) Chem. Biol. Interact. 143-144, 149-158
49. Fan, F., Germann, M. W., and Gadda, G. (2006) Biochemistry 45, 1979-1986
50. Gadda, G. (2008) Biochemistry 47, 13745-13753
51. Gadda, G., Powell, N. L., and Menon, P. (2004) Arch. Biochem. Biophys. 430, 264-273
52. Fan, F., and Gadda, G. (2005) J. Am. Chem. Soc. 127, 2067-2074
53. Finnegan, S., and Gadda, G. (2008) Biochemistry 47, 13850-13861
54. Ghanem, M., Fan, F., Francis, K., and Gadda, G. (2003) Biochemistry 42, 15179-15188
55. Ghanem, M., and Gadda, G. (2005) Biochemistry 44, 893-904
56. Rungsrisuriyachai, K., and Gadda, G. (2008) Biochemistry 47, 6762-6769
57. Cook, P. F., Blanchard, J. S., and Cleland, W. W. (1980) Biochemistry 19, 4853-4858
58. Emanuele, J. J., and Fitzpatrick, P. F. (1995) Biochemistry 34, 3710-3715
59. Grissom, C. B., and Cleland, W. W. (1988) Biochemistry 27, 2934-2943
60. Roth, J. P., and Klinman, J. P. (2003) Proc. Natl. Acad. Sci. U. S. A. 100, 62-67
61. Su, Q., and Klinman, J. P. (1999) Biochemistry 38, 8572-8581
62. Fan, F., and Gadda, G. (2007) Biochemistry 46, 6402-6408
63. Sharma, S. C., and Klinman, J. P. (2008) J Am Chem Soc 130, 17632-17633
64. Gadda, G. (2003) Biochim. Biophys. Acta 1650, 4-9
65. Cleland, W. W. (1982) Methods Enzymol. 87, 390-405
66. Cui, Q., and Karplus, M. (2002) J. Am. Chem. Soc. 124, 3093-3124
67. Marcus, R. A. (2006) Philos. Trans. R. Soc. Lond. B Biol. Sci. 361, 1445-1455
68. Ghanem, M., and Gadda, G. (2006) Biochemistry 45, 3437-3447
69. Orville, A. M., Lountos, G. T., Finnegan, S., Gadda, G., and Prabhakar, R. (2009) Biochemistry 48, 720-728
70. Bradford, M. M. (1976) Anal. Biochem. 72, 248-254