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

JBIC Journal of Biological Inorganic Chemistry - Tập 11 - Trang 261-271 - 2006
William B. Tolman1
1Department of Chemistry and Center for Metals in Biocatalysis, University of Minnesota, Minneapolis, USA

Tóm tắt

The results of studies performed in the author’s laboratory are surveyed, with particular emphasis on demonstrating the value of a multidisciplinary synthetic modeling approach for discovering new and unusual chemistry helpful for understanding the properties of the active sites of copper proteins or assessing the feasibility of mechanistic pathways they might follow during catalysis. The discussion focuses on the progress made to date toward comprehending the nitrite reductase catalytic site and mechanism, the electronic structures of copper thiolate electron transfer centers, the sulfido-bridged “CuZ” site in nitrous oxide reductase, and the processes of dioxygen binding and activation by mono- and dicopper centers in oxidases and oxygenases.

Tài liệu tham khảo

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