4-Hydroxyphenylpyruvate dioxygenase and hydroxymandelate synthase: Exemplars of the α-keto acid dependent oxygenases

Archives of Biochemistry and Biophysics

Volumn 544, Issue , 2014, Pages 58-68

  Moran, Graham R ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

Keto acid; 4 Hydroxyphenylpyruvate dioxygenase; Dioxygenase; Ferrous; Hydroxymandelate synthase; Molecular oxygen; Oxygenase

Indexed keywords

4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; DIOXYGENASE; FERROUS; HYDROXYMANDELATE SYNTHASE; MOLECULAR OXYGEN; OXYGENASE; Α-KETO ACID;

4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; ANIMALS; BACTERIA; DIOXYGENASES; HUMANS; MANDELIC ACIDS; MODELS, MOLECULAR; PROTEIN CONFORMATION; SUBSTRATE SPECIFICITY;

EID: 84893771955     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2013.10.022     Document Type: Review

References (113)

1. V. Purpero, and G.R. Moran J. Biol. Inorg. Chem. 12 2007 587 601
2. R.P. Hausinger Crit. Rev. Biochem. Mol. Biol. 39 2004 21 68
3. S.E. Hager, R.I. Gregerman, and W.E. Knox J. Biol. Chem. 225 1957 935 947
4. B.L. Goodwin Tyrosine Catabolism 1972 Oxford University Press
5. T.W. Goodwin, and E.I. Mercer Introduction to Plant Biochemistry 1983 Pergamon Press Sydney
6. J.D. Nosanchuk, and A. Casadevall Cell Microbiol. 5 2003 203 223
7. D.E. Graham, H. Xu, and R.H. White Arch. Microbiol. 180 2003 455 464
8. O.W. Choroba, D.H. Williams, and J.B. Spencer J. Am. Chem. Soc. 122 2000 5389 5390
9. B.K. Hubbard, M.G. Thomas, and C.T. Walsh Chem. Biol. 7 2000 931 942
10. S. Ahmad, J.H. Teckman, and G.T. Lueder Am. J. Ophthalmol. 134 2002 266 268
11. G. Mitchell, D.W. Bartlett, T.E. Fraser, T.R. Hawkes, D.C. Holt, J.K. Townson, and R.A. Wichert Pest. Manag. Sci. 57 2001 120 128
12. P. Sutton, C. Richards, L. Buren, and L. Glasgow Pest. Manag. Sci. 58 2002 981 984
13. J.S. Kim, T.J. Kim, O.K. Kwon, and K.Y. Cho Photosynthetica 40 2002 541 545
14. J. Secor Plant Physiol. 106 1994 1429 1433
15. P. Suwannarat, K. O'Brien, M.B. Perry, N. Sebring, I. Bernardini, M.I. Kaiser-Kupfer, B.I. Rubin, E. Tsilou, L.H. Gerber, and W.A. Gahl Metabolism 54 2005 719 728
16. P.J. McKiernan Drugs 66 2006 743 750
17. L. Serre, A. Sailland, D. Sy, P. Boudec, A. Rolland, E. Pebay-Peyroula, and C. Cohen-Addad Struct. Fold Des. 7 1999 977 988
18. J. Brownlee, P. He, G.R. Moran, and D.H. Harrison Biochemistry 47 2008 2002 2013
19. P. He, and G.R. Moran J. Inorg. Biochem. 105 2011 1259 1272
20. R.N. Armstrong Biochemistry 39 2000 13625 13632
21. Z. Zhang, J. Ren, K. Harlos, C.H. McKinnon, I.J. Clifton, and C.J. Schofield FEBS Lett. 517 2002 7 12
22. E.L. Hegg, and L. Que Jr. Eur. J. Biochem. 250 1997 625 629
23. K.D. Koehntop, J.P. Emerson, and L. Que Jr. J. Biol. Inorg. Chem. 10 2005 87 93
24. D.D. Shah, J.A. Conrad, B. Heinz, J.M. Brownlee, and G.R. Moran Biochemistry 50 2011 7694 7704
25. D.D. Shah, J.A. Conrad, and G.R. Moran Biochemistry 52 2013 6097 6107
26. J.M. Brownlee, B. Heinz, J. Bates, and G.R. Moran Biochemistry 49 2010 7218 7226
27. H.M. O'Hare, F. Huang, A. Holding, O.W. Choroba, and J.B. Spencer FEBS Lett. 580 2006 3445 3450
28. M. Gunsior, J. Ravel, G.L. Challis, and C.A. Townsend Biochemistry 43 2004 663 674
29. I. Muller, A. Kahnert, T. Pape, G.M. Sheldrick, W. Meyer-Klaucke, T. Dierks, M. Kertesz, and I. Uson Biochemistry 43 2004 3075 3088
30. I.J. Clifton, L.C. Hsueh, J.E. Baldwin, K. Harlos, and C.J. Schofield Eur. J. Biochem. 268 2001 6625 6636
31. Z. Zhang, J. Ren, D.K. Stammers, J.E. Baldwin, K. Harlos, and C.J. Schofield Nat. Struct. Biol. 7 2000 127 133
32. J.R. O'Brien, D.J. Schuller, V.S. Yang, B.D. Dillard, and W.N. Lanzilotta Biochemistry 42 2003 5547 5554
33. R.C. Wilmouth, J.J. Turnbull, R.W. Welford, I.J. Clifton, A.G. Prescott, and C.J. Schofield Structure (Camb) 10 2002 93 103
34. M.A. McDonough, K.L. Kavanagh, D. Butler, T. Searls, U. Oppermann, and C.J. Schofield J. Biol. Chem. 280 2005 41101 41110
35. J. Brownlee, K. Johnson-Winters, D.H.T. Harrison, and G.R. Moran Biochemistry 43 2004 6370 6377
36. C. Yang, J.W. Pflugrath, D.L. Camper, M.L. Foster, D.J. Pernich, and T.A. Walsh Biochemistry 43 2004 10414 10423
37. K. Johnson-Winters, V.M. Purpero, M. Kavana, and G.R. Moran Biochemistry 44 2005 7189 7199
38. V.M. Purpero, and G.R. Moran Biochemistry 45 2006 6044 6055
39. P. He, J.A. Conrad, and G.R. Moran Biochemistry 49 2010 1998 2007
40. K. Johnson-Winters, V.M. Purpero, M. Kavana, T. Nelson, and G.R. Moran Biochemistry 42 2003 2072 2080
41. M.J. Ryle, R. Padmakumar, and R.P. Hausinger Biochemistry 38 1999 15278 15286
42. J.M. Elkins, M.J. Ryle, I.J. Clifton, and J.C. Dunning Biochemistry 41 2002 5185 5192
43. M.L. Neidig, M. Kavana, G.R. Moran, and E.I. Solomon J. Am. Chem. Soc. 126 2004 4486 4487
44. E.G. Pavel, J. Zhou, R.W. Busby, M. Gunsior, C.A. Townsend, and E.I. Solomon J. Am. Chem. Soc. 120 1998 743 753
45. J. Zhou, W.L. Kelly, B.O. Bachmann, M. Gunsior, C.A. Townsend, and E.I. Solomon J. Am. Chem. Soc. 123 2001 7388 7398
46. M.L. Neidig, A. Decker, O.W. Choroba, F. Huang, M. Kavana, G.R. Moran, J.B. Spencer, and E.I. Solomon Proc. Natl. Acad. Sci. USA 103 2006 12966 12973
47. A. Wojcik, E. Broclawik, P.E. Siegbahn, and T. Borowski Biochemistry 51 2012 9570 9580
48. M.L. Neidig, C.D. Brown, M. Kavana, O.W. Choroba, J.B. Spencer, G.R. Moran, and E.I. Solomon J. Inorg. Biochem. 100 2006 2108 2116
49. T. Borowski, A. Bassan, and P.E.M. Siegbahn Biochemistry 43 2004 12331 12342
50. A.R. Diebold, C.D. Brown-Marshall, M.L. Neidig, J.M. Brownlee, G.R. Moran, and E.I. Solomon J. Am. Chem. Soc. 133 2011 18148 18160
51. J.C. Price, E.W. Barr, T.E. Glass, C. Krebs, and J.M. Bollinger Jr. J. Am. Chem. Soc. 125 2003 13008 13009
52. J.C. Price, E.W. Barr, B. Tirupati, J.M. Bollinger Jr., and C. Krebs Biochemistry 42 2003 7497 7508
53. P.J. Riggs-Gelasco, J.C. Price, R.B. Guyer, J.H. Brehm, E.W. Barr, J.M. Bollinger Jr., and C. Krebs J. Am. Chem. Soc. 126 2004 8108 8109
54. J.C. Price, E.W. Barr, L.M. Hoffart, C. Krebs, and J.M. Bollinger Jr. Biochemistry 44 2005 8138 8147
55. C. Krebs, and D. Galonic Acc. Chem. Res. 40 2007 484 492
56. L.M. Hoffart, E.W. Barr, R.B. Guyer, J.M. Bollinger Jr., and C. Krebs Proc. Natl. Acad. Sci. USA 103 2006 14738 14743
57. A. Liu, R.Y. Ho, L. Que, M.J. Ryle, B.S. Phinney, and R.P. Hausinger J. Am. Chem. Soc. 123 2001 5126 5127
58. I. Muller, C. Stuckl, J. Wakeley, M. Kertesz, and I. Uson J. Biol. Chem. 280 2005 5716 5723
59. P.F. Fitzpatrick A. Kohen, H.-H. Limbach, Isotope Effects in Chemsitry and Biology 2006 CRC Taylor & Francis Boca Raton 861 873
60. J. Retey, K. Bartl, E. Ripp, and W.E. Hull Euro. J. Biochem./FEBS 72 1977 251 257
61. G. Guroff, J.W. Daly, D.M. Jerina, J. Renson, B. Witkop, and S. Udenfriend Science 157 1967 1524 1530
62. J.W. Daly, D.M. Jerina, and B. Witkop Experientia 28 1972 1129 1264
63. D.M. Jerina, J.W. Daly, and B. Witkop J. Am. Chem. Soc. 90 1968 6523 6525
64. W.R. Bowman, W.R. Gretton, and G.W. Kirby J. Chem. Soc. Perkin 1 3 1973 218 220
65. G.R. Moran, R.S. Phillips, and P.F. Fitzpatrick Biochemistry 38 1999 16283 16289
66. P.J. Hillas, and P.F. Fitzpatrick Biochemistry 35 1996 6969 6975
67. K.H. Mitchell, C.E. Rogge, T. Gierahn, and B.G. Fox P. Natl. Acad. Sci. USA 100 2003 3784 3789
68. G.J. Kasperek, T.C. Bruice, H. Yagi, and D.M. Jerina J. Chem. Soc. Chem. Comm. 1972 784 785
69. G.R. Moran, A. Derecskei-Kovacs, P.J. Hillas, and P.F. Fitzpatrick J. Am. Chem. Soc. 122 2000 4535 4541
70. R. Leinberger, W.E. Hull, H. Simon, and J. Retey Eur. J. Biochem. 117 1981 311 318
71. H. Maeda, and D. DellaPenna Curr. Opin. Plant Biol. 10 2007 260 265
72. R. Hellyer Aust. J. Chem. 21 1968 2825 2828
73. F.E. Dayan, S.O. Duke, A. Sauldubois, N. Singh, C. McCurdy, and C. Cantrell Phytochemistry 68 2007 2004 2014
74. M. Cocchietto, N. Skert, P.L. Nimis, and G. Sava Naturwissenschaften 89 2002 137 146
75. J.G. Romagni, G. Meazza, N.P. Nanayakkara, and F.E. Dayan FEBS Lett. 480 2000 301 305
76. H. Schindler Arzneimittelforschung 7 1957 69 72
77. R. Beaudegnies, A.J. Edmunds, T.E. Fraser, R.G. Hall, T.R. Hawkes, G. Mitchell, J. Schaetzer, S. Wendeborn, and J. Wibley Bioorg. Med. Chem. 17 2009 4134 4152
78. W.J. Michaely, G.W. Kratz, US Patent 4,780,127, 1988.
79. M. Kavana, and G.R. Moran Biochemistry 42 2003 10238 10245
80. J.A. Conrad, and G.R. Moran Inorg. Chim. Acta 361 2008 1197 1201
81. M.L. Neidig, A. Decker, M. Kavana, G.R. Moran, and E.I. Solomon Biochem. Biophys. Res. Commun. 338 2005 206 214
82. E.A. Lock, M.K. Ellis, P. Gaskin, M. Robinson, T.R. Auton, W.M. Provan, L.L. Smith, M.P. Prisbylla, L.C. Mutter, and D.L. Lee J. Inherit. Metab. Dis. 21 1998 498 506
83. M.G. Hall, M.F. Wilks, W.M. Provan, S. Eksborg, and B. Lumholtz Br. J. Clin. Pharmacol. 52 2001 169 177
84. J. Gentz, R. Jagenburg, and R. Zetterström J. Pediatr. 66 1965 670 696
85. C.R. Scott Am. J. Med. Genet. C Semin. Med. Genet. 142C 2006 121 126
86. P. Russo, and S. O'Regan Am. J. Hum. Genet. 47 1990 317 324
87. E.A. Kvittingen Scand. J. Clin. Lab. Invest. Suppl. 184 1986 27 34
88. S. Lindstedt, E. Holme, E.A. Lock, O. Hjalmarson, and B. Strandvik Lancet 340 1992 813 817
89. A.E. Garrod Lancet ii 1908 73 79
90. E.A. Garrod Lancet ii 1902 1616 1620
91. J.M. Fernandez-Canon, B. Granadino, D. Beltran-Valero de Bernabe, M. Renedo, E. Fernandez-Ruiz, M.A. Penalva, and S. Rodriguez de Cordoba Nat. Genet. 14 1996 19 24
92. C. Phornphutkul, W.J. Introne, M.B. Perry, I. Bernardini, M.D. Murphey, D.L. Fitzpatrick, P.D. Anderson, M. Huizing, Y. Anikster, L.H. Gerber, and W.A. Gahl N. Engl. J. Med. 347 2002 2111 2121
93. W.J. Introne, M.B. Perry, J. Troendle, E. Tsilou, M.A. Kayser, P. Suwannarat, K.E. O'Brien, J. Bryant, V. Sachdev, J.C. Reynolds, E. Moylan, I. Bernardini, and W.A. Gahl Molec. Genet. Metab. 103 2011 307 314
94. B. Wilcken, J.W. Hammond, N. Howard, T. Bohane, C. Hocart, and B. Halpern N. Engl. J. Med. 305 1981 865 868
95. D.M. Danks, P. Tippett, and J. Rogers Acta Paediatr. Scand. 64 1975 209 214
96. F. Endo Ryoikibetsu Shokogun Shirizu 18 1998 141 143
97. A. Niederwieser, A. Matasovic, P. Tippett, and D.M. Danks Clin. Chim. Acta 76 1977 345 356
98. K. Tomoeda, H. Awata, T. Matsuura, I. Matsuda, E. Ploechl, T. Milovac, A. Boneh, C.R. Scott, D.M. Danks, and F. Endo Mol. Genet. Metab. 71 2000 506 510
99. C.B. Item, I. Mihalek, O. Lichtarge, A. Jalan, J. Vodopiutz, A. Muhl, and O.A. Bodamer Mol. Genet. Metab. 91 2007 379 383
100. O. Giardini, A. Cantani, N.G. Kennaway, and P. D'Eufemia Pediatr. Res. 17 1983 25 29
101. R. Huhn, H. Stoermer, B. Klingele, E. Bausch, A. Fois, M. Farnetani, M. Di Rocco, J. Boue, J.M. Kirk, R. Coleman, and G. Scherer Hum. Genet. 102 1998 305 313
102. R.P. Wisse, D. Wittebol-Post, G. Visser, and A. van der Lelij BMJ Case Rep. 2012 2012
103. E. Thimm, R. Richter-Werkle, G. Kamp, B. Molke, D. Herebian, D. Klee, E. Mayatepek, and U. Spiekerkoetter J. Inherit. Metab. Dis. 35 2012 263 268
104. M. Pohorecka, M. Biernacka, A. Jakubowska-Winecka, M. Biernacki, K. Kusmierska, A. Kowalik, and J. Sykut-Cegielska Pediatr. Endocrinol. Diab. Metab. 18 2012 96 100
105. H.T. Chiu, B.K. Hubbard, A.N. Shah, J. Eide, R.A. Fredenburg, C.T. Walsh, and C. Khosla Proc. Natl. Acad. Sci. USA 98 2001 8548 8553
106. K.P. Choi, N. Kendrick, and L. Daniels J. Bacteriol. 184 2002 2420 2428
107. E. Wintermeyer, M. Flugel, M. Ott, M. Steinert, U. Rdest, K.H. Mann, and J. Hacker Infect. Immun. 62 1994 1109 1117
108. S.I. Kotob, S.L. Coon, E.J. Quintero, and R.M. Weiner App. Environ. Micro. 61 1995 1620 1622
109. R.K. Ernst, D.A. D'Argenio, J.K. Ichikawa, M.G. Bangera, S. Selgrade, J.L. Burns, P. Hiatt, K. McCoy, M. Brittnacher, A. Kas, D.H. Spencer, M.V. Olson, B.W. Ramsey, S. Lory, and S.I. Miller Environ. Micro. 5 2003 1341 1349
110. A. Rodriguez-Rojas, A. Mena, S. Martin, N. Borrell, A. Oliver, and J. Blazquez Microbiology 155 2009 1050 1057 (Reading, England)
111. K.E. Keith, L. Killip, P. He, G.R. Moran, and M.A. Valvano J. Bacteriol. 189 2007 9057 9065
112. G.R. Moran, P. He, Treatment of microbial infections with compounds that inhibit 4-hydroxyphenylpyruvate dioxygenase, in: U.P. Office (Ed.), US20100227936 A1, USA, 2010.
113. L.R. Nunes, R. Costa de Oliveira, D.B. Leite, V.S. da Silva, and E. dos Reis Cell 4 2005 2115 2128