Using synthetic chemistry to understand copper protein active sites: A personal perspective

Journal of Biological Inorganic Chemistry

Volumn 11, Issue 3, 2006, Pages 261-271

  Tolman, William B ^a  

^a University of Minnesota   (United States)

Author keywords

Copper proteins; Dioxygen; Nitric oxide; Sulfide; Thiolate

Indexed keywords

COPPER DERIVATIVE; COPPER PROTEIN; NITRITE REDUCTASE; NITROUS OXIDE REDUCTASE;

BINDING SITE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT; ENZYME ACTIVATION; ENZYME ACTIVE SITE; FEASIBILITY STUDY; HEALTH SURVEY; LABORATORY; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN BINDING; SHORT SURVEY; SIGNAL TRANSDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

BINDING SITES; CATALYTIC DOMAIN; COPPER; ENZYMES; MODELS, MOLECULAR; PROTEINS;

EID: 33645548612     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-006-0078-9     Document Type: Short Survey

References (122)

1. Kaim W, Rall J (1996) Angew Chem Int Ed Engl 35:43-60
2. Ibers JA, Holm RH (1980) Science 209:223-235
3. Karlin KD (1993) Science 261:701-708
4. Holm RH, Solomon EI (2004) Chem Rev 104:347-348
5. Kitajima N (1992) Adv Inorg Chem 39:1-77
6. Mirica LM, Ottensaelder X, Stack TDP (2004) Chem Rev 104:1013-1045
7. Lewis EA, Tolman WB (2004) Chem Rev 104:1047-1076
8. Kopf M-A, Karlin KD (2000) In: Meunier B (ed) Biomimetic oxidations catalyzed by transition metal complexes. Imperial College Press, London, pp 309-362
9. Wasser IM, de Vries S, Moënne-Loccoz P, Schröder I, Karlin KD (2002) Chem Rev 102:1201-1234
10. Itoh S, Fukuzumi S (2002) Bull Chem Soc Jpn 75:2081-2095
11. Bouwman E, Driessen WL, Reedijk J (1990) Coord Chem Rev 104:143-172
12. Averill BA (1996) Chem Rev 96:2951-2964
13. Suzuki S, Kataoka K, Yamaguchi K (2000) Acc Chem Res 33:728-735
14. Eady RR, Hasnain SS (2004) In: McCleverty JA, Meyer TJ (eds) Comprehensive coordination chemistry II, vol 8. Elsevier, Amsterdam, pp 759-786
15. Godden JW, Turley S, Teller DC, Adman ET, Liu MY, Payne WJ, LeGall J (1991) Science 253:438-442
16. Suzuki S, Kohzuma T, Deligeer, Yamaguchi K, Nakamura N, Shidara S, Kobayashi K, Tagawa S (1994) J Am Chem Soc 116:11145-11146
17. Farver O, Eady RR, Abraham ZHL, Pecht I (1998) FEBS Lett 436:239-242
18. Suzuki S, Deligeer, Yamaguchi K, Kataoka K, Kobayashi K, Tagawa S, Kohzuma T, Shidara S, Iwasaki H (1997) J Biol Inorg Chem 2:265-274
19. Hulse CL, Averill BA, Tiedje JM (1989) J Am Chem Soc 111:2322-2323
20. Carrier SM, Ruggiero CE, Tolman WB, Jameson GB (1992) J Am Chem Soc 114:4407-4408
21. Ruggiero CE, Carrier SM, Antholine WE, Whittaker JW, Cramer CJ, Tolman WB (1993) J Am Chem Soc 115:11285-11298
22. Schneider JL, Carrier SM, Ruggiero CE, Young VG Jr, Tolman WB (1998) J Am Chem Soc 120:11408-11418
23. Enemark JH, Feltham RD (1974) Coord Chem Rev 13: 339-406
24. Ruggiero CE, Carrier SM, Tolman WB (1993) Angew Chem Int Ed Engl 33:895-897
25. Murphy MEP, Turley S, Adman ET (1997) J Biol Chem 272:28455-28460
26. Veselov A, Olesen K, Sienkiewicz A, Shapleigh JP, Scholes CP (1998) Biochemistry 37:6095-6105
27. Halfen JA, Tolman WB (1994) J Am Chem Soc 116:5475-5476
28. Halfen JA, Mahapatra S, Wilkinson EC, Gengenbach AJ, Young VG Jr, Que L Jr, Tolman WB (1996) J Am Chem Soc 118:763-776
29. Haselhorst G, Stoetzel S, Strassburger A, Walz W, Wieghardt K, Nuber B (1993) J Chem Soc Dalton Trans 83-90
30. Yokoyama H, Yamaguchi K, Sugimoto M, Suzuki S (2005) Eur J Inorg Chem 1435-1441
31. Coppens P, Novozhilova I, Kovalevsky A (2002) Chem Rev 102:861-883
32. Tocheva EI, Rosell FI, Mauk AG, Murphy MEP (2004) Science 304:867-870
33. Antonyuk SV, Strange RW, Sawers G, Eady RR, Hasnain SS (2005) Proc Natl Acad Sci USA 102:12041-12046
34. Wasbotten IH, Ghosh A (2005) J Am Chem Soc (in press)
35. Lu Y (2004) In: McCleverty JA, Meyer TJ (eds) Comprehensive coordination chemistry II, vol 8. Elsevier, Amsterdam, pp 91-122
36. Kroneck PMH, Antholine WA, Riester J, Zumft WG (1988) FEBS Lett 242:70-74
37. Antholine WE, Kastrau DHW, Steffens GCM, Buse G, Zumft WG, Kroneck PMH (1992) Eur J Biochem 209:875-881
38. Iwata S, Ostermeier C, Ludwig B, Michel H (1995) Nature 376:660-669
39. Tsukihara T, Aoyama H, Yamashita E, Tomizaki T, Yamaguchi H, Shinzawa-Itoh K, Nakashima R, Yaono R, Yoshikawa S (1995) Science 269:1069-1074
40. Gray HB, Malmstrom BG, Williams RJP (2000) J Biol Inorg Chem 551-559
41. Randall DW, Gamelin DR, LaCroix LB, Solomon EI (2000) J Biol Inorg Chem 5:16-19
42. Dennison C (2005) Dalton Trans 3436-3442
43. Yanagisawa S, Dennison C (2005) J Am Chem Soc 127:16453-16459
44. Solomon EI, Szilagyi RK, DeBeerGeorge S, Basumallick L (2004) Chem Rev 104:419-458
45. Mandal S, Das G, Sinah R, Shukla R, Bharadwaj PK (1997) Coord Chem Rev 160:191-235
46. Kitajima N, Fujisawa K, Moro-oka Y (1990) J Am Chem Soc 112:3210-3212
47. Kitajima N, Fujisawa K, Tanaka M, Moro-oka Y (1992) J Am Chem Soc 114:9232-9233
48. Randall DW, George SD, Hedman B, Hodgson KO, Fujisawa K, Solomon EI (2000) J Am Chem Soc 122:11620-11631
49. Holland PL, Tolman WB (1999) J Am Chem Soc 121:7270-7271
50. Holland PL, Tolman WB (2000) J Am Chem Soc 122:6331-6332
51. Spencer DJE, Reynolds AM, Holland PL, Jazdzewski BA, Duboc-Toia C, Pape LL, Yokota S, Tachi Y, Itoh S, Tolman WB (2002) Inorg Chem 41:6307-6321
52. Randall DW, DeBeer S, Holland PL, Hedman B, Hodgson KO, Tolman WB, Solomon EI (2000) J Am Chem Soc 122:11632-11648
53. Chowdhury A, Penteanu LA, Holland PL, Tolman WB (2002) J Phys Chem B 106:3007-3012
54. Karlin KD, Tyeklár Z (eds) (1993) Bioinorganic chemistry of copper. Chapman & Hall, New York
55. Farrar JA, Neese F, Lappalainen P, Kroneck PMH, Saraste M, Zumft WG, Thomson AJ (1996) J Am Chem Soc 118:11501-11514
56. Houser RP, Young VG Jr, Tolman WB (1996) J Am Chem Soc 118:2101-2102
57. Williams KR, Gamelin DR, LaCroix LB, Houser RP, Tolman WB, Mulder TC, de Vries S, Hedman B, Hodgson KO, Solomon EI (1997) J Am Chem Soc 119:613-614
58. Gamelin DR, Randall DW, Hay MT, Houser RP, Mulder TC, Canters GW, de Vries S, Tolman WB, Lu Y, Solomon EI (1998) J Am Chem Soc 120:5246-5263
59. George SD, Metz M, Szilagyi RK, Wang H, Cramer SP, Lu Y, Tolman WB, Hedman B, Hodgson KO, Solomon EI (2001) J Am Chem Soc 123:5757-5767
60. Blackburn NJ, Barr ME, Woodruff WH, Ooost Jvd, de Vries S (1994) Biochemistry 33:10401-10407
61. Zumft WG (1997) Microbiol Rev 61:533-616
62. Chen P, Gorelsky SI, Ghosh S, Solomon EI (2004) Angew Chem Int Ed Engl 43:4132-4140
63. Brown K, Djinovic-Carugo K, Haltia T, Cabrito I, Saraste M, Moura JJG, Moura I, Tegoni M, Cambillau C (2000) J Biol Chem 275:41133-41136
64. Haltia T, Brown K, Tegoni M, Cambillau C, Saraste M, Mattila K, Djinovic-Carugo K (2003) Biochem J 369:77-88
65. Alvarez ML, Ai J, Zumft W, Sanders-Loehr J, Dooley DM (2001) J Am Chem Soc 123:576-587
66. Rasmussen T, Berks BC, Sanders-Loehr J, Dooley DM, Zumft WG, Thomson AJ (2000) Biochemistry 39:12753-12756
67. Chen P, Cabrito I, Moura JJG, Moura I, Solomon EI (2002) J Am Chem Soc 124:10497-10507
68. Chen P, DeBeer George S, Cabrito I, Antholine WE, Moura JJG, Moura I, Hedman B, Hodgson KO, Solomon EI (2002) J Am Chem Soc 124:744-745
69. Ghosh S, Gorelsky SI, Chen P, Cabrito I, Moura JJG, Moura I, Solomon EI (2003) J Am Chem Soc 125:15708-15709
70. Chan JM, Bollinger JA, Grewell CL, Dooley DM (2004) J Am Chem Soc 126:3030-3031
71. Rasmussen T, Brittain T, Berks BC, Watmough NJ, Thomson AJ (2005) Dalton Trans 3501-3506
72. Gorelsky SI, Ghosh S, Solomon EI (2006) J Am Chem Soc 128:278-290
73. Dehnen S, Eichhöfer A, Fenske D (2002) Eur J Inorg Chem 279-317
74. Brown EC, Aboelella NW, Reynolds AM, Aullón G, Alvarez S, Tolman WB (2004) Inorg Chem 43:3335-3337
75. Brown EC, York JT, Antholine WE, Ruiz E, Alvarez S, Tolman WB (2005) J Am Chem Soc 127:13752-13753
76. York JT, Brown EC, Tolman WB (2005) Angew Chem Int Ed Engl (in press)
77. Fujisawa K, Moro-oka Y, Kitajima N (1994) J Chem Soc Chem Commun 623-624
78. Helton ME, Chen P, Paul PP, Tyeklar Z, Sommer RD, Zakharov LN, Rheingold AL, Solomon EI, Karlin KD (2003) J Am Chem Soc 125:1160-1161
79. Chen P, Fujisawa K, Helton ME, Karlin KD, Solomon EI (2003) J Am Chem Soc 125:6394-6408
80. Helton ME, Maiti D, Zakharov LN, Rheingold AL, Porco JA Jr, Karlin KD (2006) Angew Chem Int Ed (early view)
81. Cole AP, Root DE, Mukherjee P, Solomon EI, Stack TDP (1996) Science 273:1848-1850
82. Root DE, Henson MJ, Machonkin T, Mukherjee P, Stack TDP, Solomon EI (1998) J Am Chem Soc 120:4982-4990
83. Magnus KA, Ton-That H, Carpenter JE (1994) Chem Rev 94:727-735
84. Solomon EI, Sundaram UM, Machonkin TE (1996) Chem Rev 96:2563-2605
85. Solomon EI, Chen P, Metz M, Lee S-K, Palmer AE (2001) Angew Chem Int Ed Engl 40:4570-4590
86. Messerschmidt A (ed) (1997) Multi-copper oxidases. World Scientific, Singapore
87. Lieberman RL, Rosenzweig AC (2005) Dalton Trans 3390-3396
88. Sánchez-Ferrer A, Rodríguez-Lopez JN, García- Cánovas F, García-Carmona F (1995) Biochim Biophys Acta 1247:1-11
89. Schindler S (2000) Eur J Inorg Chem 2311-2326
90. Itoh S (2004) In: McCleverty JA, Meyer TJ (eds) Comprehensive coordination chemistry II, vol 8. Elsevier, Amsterdam, pp 369-393
91. Hatcher L, Karlin KD (2004) J Biol Inorg Chem 9:669-683
92. Jacobson RR, Tyeklár Z, Farooq A, Karlin KD, Liu S, Zubieta J (1988) J Am Chem Soc 110:3690-3692
93. Kitajima N, Fujisawa K, Moro-oka Y (1989) J Am Chem Soc 111:8975-8976
94. Tolman WB (1997) Acc Chem Res 30:227-237
95. Halfen JA, Mahapatra S, Wilkinson EC, Kaderli S, Young VG Jr, Que L Jr, Zuberbühler AD, Tolman WB (1996) Science 271:1397-1400
96. Decker H, Dillinger R, Tuczek F (2000) Angew Chem Int Ed Engl 39:1591-1595
97. Pidcock E, Obias HV, Zhang CX, Karlin KD, Solomon EI (1998) J Am Chem Soc 120:7841-7847 and references cited therein
98. Palavicini S, Granata A, Monzani E, Casella L (2005) J Am Chem Soc 127:18031-18036
99. Holland PL, Rodgers KR, Tolman WB (1999) Angew Chem Int Ed Engl 38:1139-1142
100. Holland PL, Tolman WB (1999) Coord Chem Rev 190-192:855-869
101. Siegbahn PEM (2003) J Biol Inorg Chem 8:567-576
102. Rode MF, Werner H-J (2005) Theor Chem Acc 114:309-317
103. Cramer CJ, Wloch M, Piecuch P, Puzzarini C, Gagliardi L (2006) J Phys Chem (in press)
104. Mirica LM, Vance M, Rudd DJ, Hedman B, Hodgson KO, Solomon EI, Stack TDP (2005) Science 308:1890-1892
105. Klinman JP (1996) Chem Rev 96:2541-2561
106. Halcrow MA (2004) In: McCleverty JA, Meyer TJ (eds) Comprehensive coordination chemistry II. Elsevier, Amsterdam, pp 395-436
107. Stewart LC, Klinman JP (1988) Annu Rev Biochem 57:551-592
108. Prigge ST, Mains RE, Eipper BA, Amzel LM (2000) Cell Mol Life Sci 57:1236-1259
109. Evans JP, Ahn K, Klinman JP (2003) J Biol Chem 278:49691-49698
110. Chen P, Solomon EI (2004) J Am Chem Soc 126:4991-5000
111. Prigge ST, Eipper BA, Mains RE, Amzel LM (2004) Science 304:864-867
112. Fujisawa K, Tanaka M, Moro-oka Y, Kitajima N (1994) J Am Chem Soc 116:12079-12080
113. Chen P, Root DE, Campochiaro C, Fujisawa K, Solomon EI (2003) J Am Chem Soc 125:466-474
114. Cramer CJ, Tolman WB, Theopold KH, Rheingold AL (2003) Proc Natl Acad Sci USA 100:3635
115. Spencer DJE, Aboelella NW, Reynolds AM, Holland PL, Tolman WB (2002) J Am Chem Soc 124:2108-2809
116. Spencer DJE, Reynolds AM, Holland PL, Jazdzewski BA, Duboc-Toia C, Pape LL, Yokota S, Tachi Y, Itoh S, Tolman WB (2002) Inorg Chem 41:6307-6321
117. Aboelella NW, Lewis EA, Reynolds AM, Brennessel WW, Cramer CJ, Tolman WB (2002) J Am Chem Soc 124:10660-10661
118. Aboelella NW, Kryatov SV, Gherman BF, Brennessel WW, Young VG Jr, Sarangi R, Rybak-Akimova EV, Hodgson KO, Hedman B, Solomon EI, Cramer CJ, Tolman WB (2004) J Am Chem Soc 126:16896-16911
119. Reynolds AM, Gherman BF, Cramer CJ, Tolman WB (2005) Inorg Chem 44:6989-6997
120. Gherman BF, Cramer CJ (2004) Inorg Chem 43:7281-7283
121. Aboelella NW, York JT, Reynolds AM, Fujita K, Kinsinger CR, Cramer CJ, Riordan CG, Tolman WB (2004) Chem Commun 1716-1717
122. Aboelella NW, Gherman BF, Hill LMR, York JT, Holm N, Young VG Jr, Cramer CJ, Tolman WB (2006) J Am Chem Soc (accepted)