The diverse and pervasive chemistries of the α-keto acid dependent enzymes

Journal of Biological Inorganic Chemistry

Volumn 12, Issue 5, 2007, Pages 587-601

  Purpero, Vincent ^a,b   Moran, Graham R ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Keto acid; Ferrous; Molecular oxygen; Mononuclear; Oxygenase

Indexed keywords

ALPHA KETO ACID DEPENDENT OXYGENASE; ISOENZYME; UNCLASSIFIED DRUG;

DEALKYLATION; ENZYME CHEMISTRY; ENZYME KINETICS; EPIMERIZATION; HALOGENATION; HYDROXYLATION; ISOENZYME ANALYSIS; OXIDATION KINETICS; PRIORITY JOURNAL; SHORT SURVEY;

ANIMALS; ENZYMES; HUMANS; IRON; KETO ACIDS; MODELS, MOLECULAR; OXYGEN; OXYGENASES;

EID: 34249869010     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-007-0231-0     Document Type: Short Survey

References (111)

1. Feig AL, Lippard SJ (1994) Chem Rev 94:759-805
2. Hutton JJ Jr, Trappel AL, Udenfriend S (1966) Biochem Biophys Res Commun 24:179-184
3. Abbott MT, Udenfriend S (1974) Alpha-ketoglutarate-coupled dioxygenases, molecular mechanisms of oxygen activation, Academic, New York
4. Hausinger RP (2004) Crit Rev Biochem Mol Biol 39:21-68
5. Que LJ, Ho RYN (1996) ChemRev 96:2607-2524
6. Hanauske-Abel HM, Gunzler V (1982) J Theor Biol 94:421-455
7. Solomon EI, Brunold TC, Davis MI, Kemsley JN, Lee SK, Lehnert N, Neese F, Skulan AJ, Yang YS, Zhou J (2000) Chem Rev 100:235-350
8. Hegg EL, Que L Jr (1997) Eur J Biochem 250:625-629
9. Muller I, Kahnert A, Pape T, Sheldrick GM, Meyer-Klaucke W, Dierks T, Kertesz M, Uson I (2004) Biochemistry 43:3075-3088
10. Clifton IJ, Hsueh LC, Baldwin JE, Harlos K, Schofield CJ (2001) Eur J Biochem 268:6625-6636
11. Valegard K, van Scheltinga AC, Lloyd MD, Hara T, Ramaswamy S, Perrakis A, Thompson A, Lee HJ, Baldwin JE, Schofield CJ, Hajdu J, Andersson I (1998) Nature 394:805-809
12. Zhang Z, Ren J, Stammers DK, Baldwin JE, Harlos K, Schofield CJ (2000) Nat Struct Biol 7:127-133
13. O'Brien JR, Schuller DJ, Yang VS, Dillard BD, Lanzilotta WN (2003) Biochemistry 42:5547-5554
14. Wilmouth RC, Turnbull JJ, Welford RW, Clifton IJ, Prescott AG, Schofield CJ (2002) Structure 10:93-103
15. Pavel EG, Zhou J, Busby RW, Gunsior M, Townsend CA, Solomon EI (1998) J Am Chem Soc 120:743-753
16. Johnson-Winters K, Purpero VM, Kavana M, Nelson T, Moran GR (2003) Biochemistry 42:2072-2080
17. Solomon EI, Decker A, Lehnert N (2003) Proc Natl Acad Sci USA 100:3589-3594
18. Cosper NJ, Stalhandske CM, Saari RE, Hausinger RP, Scott RA (1999) J Biol Inorg Chem 4:122-129
19. Neidig ML, Kavana M, Moran GR, Solomon EI (2004) J Am Chem Soc 126:4486-4487
20. Neidig ML, Decker A, Choroba OW, Huang F, Kavana M, Moran GR, Spencer JB, Solomon EI (2006) Proc Natl Acad Sci USA 103:12966-12973
21. Holme E (1975) Biochemistry 14:4999-5003
22. Rundgren M (1977) J Biol Chem 252:5094-5099
23. Tuderman L, Myllyla R, Kivirikko KI (1977) Eur J Biochem 80:341-348
24. Myllyla R, Tuderman L, Kivirikko KI (1977) Eur J Biochem 80:349-357
25. Puistola U, Turpeenniemi-Hujanen TM, Myllyla R, Kivirikko KI (1980) Biochim Biophys Acta 611:51-60
26. De Carolis E, De Luca V (1993) J Biol Chem 268:5504-5511
27. Valegard K, Terwisscha van Scheltinga AC, Dubus A, Ranghino G, Oster LM, Hajdu J, Andersson I (2004) Nat Struct Mol Biol 11:95-101
28. Dann CE 3rd, Bruick RK, Deisenhofer J (2002) Proc Natl Acad Sci USA 99:15351-15356
29. Elkins JM, Hewitson KS, McNeill LA, Seibel JF, Schlemminger I, Pugh CW, Ratcliffe PJ, Schofield CJ (2003) J Biol Chem 278:1802-1806
30. Clifton IJ, Doan LX, Sleeman MC, Topf M, Suzuki H, Wilmouth RC, Schofield CJ (2003) J Biol Chem 278:20843-20850
31. McDonough MA, Kavanagh KL, Butler D, Searls T, Oppermann U, Schofield CJ (2005) J Biol Chem 280:41101-41110
32. Ryle MJ, Padmakumar R, Hausinger RP (1999) Biochemistry 38:15278-15286
33. Zhou J, Kelly WL, Bachmann BO, Gunsior M, Townsend CA, Solomon EI (2001) J Am Chem Soc 123:7388-7398
34. Ho RY, Mehn MP, Hegg EL, Liu A, Ryle MJ, Hausinger RP, Que L Jr (2001) J Am Chem Soc 123:5022-5029
35. Davis MI, Wasinger EC, Decker A, Pau MYM, Vaillancourt FH, Bolin JT, Eltis LD, Hedman B, Hodgson KO, Solomon EI (2003) J Am Chem Soc 125:11214-11227
36. Eltis LD, Bolin JT (1996) J Bacteriol 178:5930-5937
37. Serre L, Sailland A, Sy D, Boudec P, Rolland A, Pebay-Peyroula E, Cohen-Addad C (1999) Struct Fold Des 7:977-988
38. Moran GR (2005) Arch Biochem Biophys 433:117-128
39. Elkins JM, Ryle MJ, Clifton IJ, Dunning Hotopp JC, Lloyd JS, Burzlaff NI, Baldwin JE, Hausinger RP, Roach PL (2002) Biochemistry 41:5185-5192
40. Yu B, Edstrom WC, Benach J, Hamuro Y, Weber PC, Gibney BR, Hunt JF (2006) Nature 439:879-884
41. Koivisto P, Duncan T, Lindahl T, Sedgwick B (2003) J Biol Chem 278:44348-44354
42. Ryle MJ, Liu A, Muthukumaran RB, Ho RY, Koehntop KD, McCracken J, Que L Jr, Hausinger RP (2003) Biochemistry 42:1854-1862
43. Muller I, Stuckl C, Wakeley J, Kertesz M, Uson I (2005) J Biol Chem 280:5716-5723
44. Neidig ML, Brown CD, Kavana M, Choroba OW, Spencer JB, Moran GR, Solomon EI (2006) J Inorg Biochem 100:2108-2116
45. Zhang Z, Ren J, Harlos K, McKinnon CH, Clifton IJ, Schofield CJ (2002) FEBS Lett 517:7-12
46. Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M (2006) Chem Biol Interact 160:1-40
47. Weiss SJ (1982) J Biol Chem 257:2947-2953
48. Simon RH, Scoggin CH, Patterson D (1981) J Biol Chem 256:7181-7186
49. Freeman BA, Crapo JD (1982) Lab Invest 47:412-426
50. Lange T, Kegler C, Hedden P, Phillips AL, Graebe JE (1997) Physiol Plant 100:543-549
51. Brownlee J, Kayunta J-W, Harrison DHT, Moran GR (2004) Biochemistry 43:6370-6377
52. Fritze IM, Linden L, Freigang J, Auerbach G, Huber R, Steinbacher S (2004) Plant Physiol 134:1388-1400
53. Yang C, Pflugrath JW, Camper DL, Foster ML, Pernich DJ, Walsh TA (2004) Biochemistry 43:10414-10423
54. Oster LM, van Scheltinga AC, Valegard K, Hose AM, Dubus A, Hajdu J, Andersson I (2004) J Mol Biol 343:157-171
55. Lee HJ, Lloyd MD, Harlos K, Clifton IJ, Baldwin JE, Schofield CJ (2001) J Mol Biol 308:937-948
56. Lloyd MD, Lee HJ, Harlos K, Zhang ZH, Baldwin JE, Schofield CJ, Charnock JM, Garner CD, Hara T, Terwisscha van Scheltinga AC, Valegard K, Viklund JA, Hajdu J, Andersson I, Danielsson A, Bhikhabhai R (1999) J Mol Biol 287:943-960
57. Lee C, Kim SJ, Jeong DG, Lee SM, Ryu SE (2003) J Biol Chem 278:7558-7563
58. Ryle MJ, Koehntop KD, Liu AM, Que L, Hausinger RP (2003) Proc Natl Acad Sci USA 100:3790-3795
59. Myllyla R, Kuutti-Savolainen ER, Kivirikko KI (1978) Biochem Biophys Res Commun 83:441-448
60. Ge Y, Lawhorn BG, ElNaggar M, Sze SK, Begley TP, McLafferty FW (2003) Protein Sci 12:2320-2326
61. Rao NV, Adams E (1978) J Biol Chem 253:6327-6330
62. De Jong L, Kemp A (1984) Biochim Biophys Acta 787:105-111
63. Counts DF, Cardinale GJ, Udenfriend S (1978) Proc Natl Acad Sci USA 75:2145-2149
64. Holme E, Lindstedt S (1982) Biochim Biophys Acta 704:278-283
65. Myllyharju J, Kivirikko KI (1997) EMBO J 16:1173-1180
66. Lindstedt S, Rundgren M (1982) J Biol Chem 257:11922-11931
67. Bradley FC, Lindstedt S, Lipscomb JD, Que L Jr, Roe AL, Rundgren M (1986) J Biol Chem 261:11693-11696
68. Liu A, Ho RY, Que L, Ryle MJ, Phinney BS, Hausinger RP (2001) J Am Chem Soc 123:5126-5127
69. Henshaw TF, Feig M, Hausinger RP (2004) J Inorg Biochem 98:856-861
70. Sundheim O, Vagbo CB, Bjoras M, Sousa MM, Talstad V, Aas PA, Drablos F, Krokan HE, Tainer JA, Slupphaug G (2006) EMBO J 25:3389-3397
71. Purpero VM, Moran GR (2006) Biochemistry 45:6044-6055
72. Arciero DM, Orville AM, Lipscomb JD (1985) J Biol Chem 260:14035-14044
73. Grzyska PK, Ryle MJ, Monterosso GR, Liu J, Ballou DP, Hausinger RP (2005) Biochemistry 44:3845-3855
74. Johnson-Winters K, Purpero VM, Kavana M, Moran GR (2005) Biochemistry 44:7189-7199
75. Price JC, Barr EW, Tirupati B, Bollinger JM Jr, Krebs C (2003) Biochemistry 42:7497-7508
76. Price JC, Barr EW, Glass TE, Krebs C, Bollinger JM Jr (2003) J Am Chem Soc 125:13008-13009
77. Hoffart LM, Barr EW, Guyer RB, Bollinger JM Jr, Krebs C (2006) Proc Natl Acad Sci USA 103:14738-14743
78. Galonic DP, Barr EW, Walsh CT, Bollinger JM Jr, Krebs C (2007) Nat Chem Biol 3:113-116
79. Debrunner PG (1989) Iron porphyrins, VCH, New York
80. Grapperhaus CA, Mienert B, Bill E, Weyhermuller T, Wieghardt K (2000) Inorg Chem 39:5306-5317
81. Lim MH, Rohde JU, Stubna A, Bukowski MR, Costas M, Ho RYN, Munck E, Nam W, Que L (2003) Proc Natl Acad Sci USA 100:3665-3670
82. Rohde JU, In JH, Lim MH, Brennessel WW, Bukowski MR, Stubna A, Munck E, Nam W, Que L Jr (2003) Science 299:1037-1039
83. Proshlyakov DA, Henshaw TF, Monterosso GR, Ryle MJ, Hausinger RP (2004) J Am Chem Soc 126:1022-1023
84. Kitagawa T, Mizutani Y (1994) Coordin Chem Rev 135:685-735
85. Nakamoto K (2002) Coord Chem Rev 226:153-165
86. Wolter T, Meyer-Klaucke W, Muther M, Mandon D, Winkler H, Trautwein AX, Weiss R (2000) J Inorg Biochem 78:117-122
87. Penner-Hahn JE, McMurry TJ, Renner M, Latos-Grazynsky L, Eble KS, Davis IM, Balch AL, Groves JT, Dawson JH, Hodgson KO (1983) J Biol Chem 258:12761-12764
88. Riggs-Gelasco PJ, Price JC, Guyer RB, Brehm JH, Barr EW, Bollinger JM Jr, Krebs C (2004) J Am Chem Soc 126:8108-8109
89. Costas M, Mehn MP, Jensen MP, Que L (2004) Chem Rev 104:939-986
90. Lloyd MD, Merritt KD, Lee V, Sewell TJ, Wha-Son B, Baldwin JE, Schofield CJ (1999) Tetrahedron 55:10201-10220
91. Flashman E, Schofield CJ (2007) Nat Chem Biol 3:86-87
92. Neidig ML, Decker A, Kavana M, Moran GR, Solomon EI (2005) Biochem Biophys Res Commun 338:206-214
93. Borowski T, Bassan A, Siegbahn PEM (2004) Biochemistry 43:12331-12342
94. Borowski T, Bassan A, Siegbahn PEM (2004) Inorg Chem 43:3277-3291
95. Price JC, Barr EW, Hoffart LM, Krebs C, Bollinger JM Jr (2005) Biochemistry 44:8138-8147
96. Topf M, Sandala GM, Smith DM, Schofield CJ, Easton CJ, Radom L (2004) J Am Chem Soc 126:9932-9933
97. Vaillancourt FH, Yeh E, Vosburg DA, O'Connor SE, Walsh CT (2005) Nature 436:1191-1194
98. Welford RW, Clifton IJ, Turnbull JJ, Wilson SC, Schofield CJ (2005) Org Biomol Chem 3:3117-3126
99. Hirao H, Kumar D, Que L Jr, Shaik S (2006) J Am Chem Soc 128:8590-8606
100. Bukowski MR, Comba P, Lienke A, Limberg C, Lopez de Laorden C, Mas-Balleste R, Merz M, Que L Jr (2006) Angew Chem Int Ed Engl 45:3446-3449
101. Kumar D, Hirao H, Que L, Shaik S (2005) J Am Chem Soc 127:8026-8027
102. Metcalf WW, Wolfe RS (1998) J Bacteriol 180:5547-5558
103. Pascal RA Jr, Oliver MA, Chen YC (1985) Biochemistry 24:3158-3165
104. Lindstedt G, Lindstedt S, Nordin I (1977) Biochemistry 16:2181-2188
105. Frey M, Huber K, Park WJ, Sicker D, Lindberg P, Meeley RB, Simmons CR, Yalpani N, Gierl A (2003) Phytochemistry 62:371-376
106. Sono M, Roach MP, Coulter ED, Dawson JH (1996) Chem Rev 96:2841-2888
107. Gunsior M, Ravel J, Challis GL, Townsend CA (2004) Biochemistry 43:663-674
108. Borowski T, Broclawik E, Schofield CJ, Siegbahn PE (2006) J Comput Chem 27:740-748
109. Vaillancourt FH, Yin J, Walsh CT (2005) Proc Natl Acad Sci USA 102:10111-10116
110. Galonic DP, Vaillancourt FH, Walsh CT (2006) J Am Chem Soc 128:3900-3901
111. Blasiak LC, Vaillancourt FH, Walsh CT, Drennan CL (2006) Nature 440:368-371