Theoretical study of the hydroxylation of phenolates by the Cu 2O2(N,N′-dimethylethylenediamine)2 2+ complex

Journal of Biological Inorganic Chemistry

Volumn 14, Issue 2, 2009, Pages 229-242

  Güell, Mireia ^a,b   Luis, Josep M ^a   Solà, Miquel ^a   Siegbahn, Per E M ^b  

^a Institut de Quimica Computacional   (Spain)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Biomimetic metal complexes; Copper enzymes; Density functional theory; O2 cleavage; Tyrosinase

Indexed keywords

BIOMIMETIC MATERIAL; COPPER OXIDE; ETHYLENEDIAMINE DERIVATIVE; MONOPHENOL MONOOXYGENASE; N,N DIMETHYLETHYLENEDIAMINE; PHENOL; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL BOND; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; PROTEIN STRUCTURE; REACTION ANALYSIS; THEORETICAL STUDY;

CATALYSIS; COMPUTER SIMULATION; HYDROXYBENZOIC ACIDS; HYDROXYLATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; QUINONES; STEREOISOMERISM;

EID: 58849159102     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-008-0443-y     Document Type: Article

References (72)

1. EI Solomon UM Sundaram TE Machonkin 1996 Chem Rev 96 2563 2605
2. EI Solomon MJ Baldwin MD Lowery 1992 Chem Rev 92 521 542
3. WS Oetting 2000 Pigment Cell Res 13 320 325
4. YM Xu AH Stokes R Roskoski KE Vrana 1998 J Neurosci Res 54 691 697
5. M Asanuma I Miyazaki N Ogawa 2003 Neurotox Res 5 165 176
6. S Parvez M Kang HS Chung H Bae 2007 Phytother Res 21 805 816
7. RO de Faria VR Moure M Amazonas N Krieger DA Mitchell 2007 Food Technol Biotechnol 45 287 294
8. A Sánchez-Ferrer JN Rodríguez-López F García-Cánovas F García-Carmona 1995 Biochim Biophys Acta Protein Struct Mol Enzymol 1247 1 11
9. DE Wilcox AG Porras YT Hwang K Lerch ME Winkler EI Solomon 1985 J Am Chem Soc 107 4015 4027
10. PEM Siegbahn 2003 J Biol Inorg Chem 8 567 576
11. Y Matoba T Kumagai A Yamamoto H Yoshitsu M Sugiyama 2006 J Biol Chem 281 8981 8990
12. PK Ross EI Solomon 1990 J Am Chem Soc 112 5871 5872
13. PK Ross EI Solomon 1991 J Am Chem Soc 113 3246 3259
14. MJ Baldwin DE Root JE Pate K Fujisawa N Kitajima EI Solomon 1992 J Am Chem Soc 114 10421 10431
15. NC Eickman EI Solomon JA Larrabee TG Spiro K Lerch 1978 J Am Chem Soc 100 6529 6531
16. EA Lewis WB Tolman 2004 Chem Rev 104 1047 1076
17. LQ Hatcher KD Karlin 2004 J Biol Inorg Chem 9 669 683
18. LQ Hatcher KD Karlin 2006 Adv Inorg Chem Bioinorg Stud 58 131 184
19. M Costas X Ribas A Poater JM López Balvuena R Xifra A Company M Duran M Solà A Llobet M Corbella MA Usón J Mahía X Solans X Shan J Benet-Buchholz 2006 Inorg Chem 45 3569 3581
20. X Ribas R Xifra T Parella A Poater M Solà A Llobet 2006 Angew Chem Int Ed 45 2941 2944
21. W Brackman E Havinga 1955 Recl Trav Chim Pays Bas 74 1021 1039
22. W Brackman E Havinga 1955 Recl Trav Chim Pays Bas 74 1070 1080
23. W Brackman E Havinga 1955 Recl Trav Chim Pays Bas 74 1100 1106
24. W Brackman E Havinga 1955 Recl Trav Chim Pays Bas 74 1107 1118
25. W Brackman E Havinga 1955 Recl Trav Chim Pays Bas 74 937 955
26. KD Karlin RW Cruse Y Gultneh JC Hayes J Zubieta 1984 J Am Chem Soc 106 3372 3374
27. MS Nasir BI Cohen KD Karlin 1992 J Am Chem Soc 114 2482 2494
28. KD Karlin MS Nasir BI Cohen RW Cruse S Kaderli AD Zuberbuhler 1994 J Am Chem Soc 116 1324 1336
29. E Pidcock HV Obias CX Zhang KD Karlin EI Solomon 1998 J Am Chem Soc 120 7841 7847
30. S Palavicini A Granata E Monzani L Casella 2005 J Am Chem Soc 127 18031 18036
31. LM Mirica M Vance DJ Rudd B Hedman KO Hodgson EI Solomon TDP Stack 2005 Science 308 1890 1892
32. LM Mirica X Ottenwaelder TDP Stack 2004 Chem Rev 104 1013 1045
33. L Que WB Tolman 2002 Angew Chem Int Ed 41 1114 1137
34. AD Becke 1993 J Chem Phys 98 5648 5652
35. CT Lee WT Yang RG Parr 1988 Phys Rev B 37 785 789
36. Schrödinger (2003) Jaguar 5.5. Schrödinger, Portland
37. PJ Hay WR Wadt 1985 J Chem Phys 82 299 310
38. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski G, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03. Gaussian, Pittsburgh
39. TH Dunning 1989 J Chem Phys 90 1007 1023
40. DE Woon TH Dunning 1994 J Chem Phys 100 2975 2988
41. DJ Tannor B Marten R Murphy RA Friesner D Sitkoff A Nicholls M Ringnalda WA Goddard B Honig 1994 J Am Chem Soc 116 11875 11882
42. B Marten K Kim C Cortis RA Friesner RB Murphy MN Ringnalda D Sitkoff B Honig 1996 J Phys Chem 100 11775 11788
43. LA Curtiss K Raghavachari PC Redfern JA Pople 2000 J Chem Phys 112 7374 7383
44. PEM Siegbahn MRA Blomberg 1999 Annu Rev Phys Chem 50 221 249
45. O Salomon M Reiher BA Hess 2002 J Chem Phys 117 4729 4737
46. M Reiher O Salomon BA Hess 2001 Theor Chem Acc 107 48 55
47. CJ Cramer WB Tolman 2007 Acc Chem Res 40 601 608
48. JL Lewin DE Heppner CJ Cramer 2007 J Biol Inorg Chem 12 1221 1234
49. CJ Cramer A Kinal M Wloch P Piecuch L Gagliardi 2006 J Phys Chem A 110 11557 11568
50. CJ Cramer A Kinal M Wloch P Piecuch L Gagliardi 2007 J Phys Chem A 111 4871
51. PEM Siegbahn 2003 J Biol Inorg Chem 8 577 585
52. CJ Cramer M Wloch P Piecuch C Puzzarini L Gagliardi 2006 J Phys Chem A 110 1991 2004
53. PA Malmqvist K Pierloot ARM Shahi CJ Cramer L Gagliardi 2008 J Chem Phys 128 204109 204110
54. Gherman B, Cramer C (2008) Coord Chem Rev. doi: 10.1016/j.ccr.2007.11.018
55. Mirica L (2005) PhD thesis, Standford University. Available via the ProQuest database, UMI # 3162369
56. LM Mirica DJ Rudd MA Vance EI Solomon KO Hodgson B Hedman TDP Stack 2006 J Am Chem Soc 128 2654 2665
57. AD Becke 1988 Phys Rev A 38 3098 3100
58. JP Perdew JA Chevary SH Vosko KA Jackson MR Pederson DJ Singh C Fiolhais 1992 Phys Rev B 46 6671 6687
59. JP Perdew K Burke Y Wang 1996 Phys Rev B 54 16533 16539
60. PJ Stephens FJ Devlin CF Chabalowski MJ Frisch 1994 J Phys Chem 98 11623 11627
61. SH Vosko L Wilk M Nusair 1980 Can J Phys 58 1200 1211
62. RH Hertwig W Koch 1997 Chem Phys Lett 268 345 351
63. BF Gherman WB Tolman CJ Cramer 2006 J Comput Chem 27 1950 1961
64. K Burke M Ernzerhof JP Perdew 1997 Chem Phys Lett 265 115 120
65. AD Becke 1996 J Chem Phys 104 1040 1046
66. Atkins P, De Paula J (2006) Physical chemistry. Oxford University Press, Oxford
67. V Mahadevan MJ Henson EI Solomon TDP Stack 2000 J Am Chem Soc 122 10249 10250
68. LQ Hatcher MA Vance AAN Sarjeant EI Solomon KD Karlin 2006 Inorg Chem 45 3004 3013
69. S Itoh M Taki H Nakao PL Holland WB Tolman L Que S Fukuzumi 2000 Angew Chem Int Ed 39 398 400
70. H Naka Y Kondo S Usui Y Hashimoto M Uchiyama 2007 Adv Synth Catal 349 595 600
71. RS Himmelwright NC Eickman CD Lubien K Lerch EI Solomon 1980 J Am Chem Soc 102 7339 7344
72. ME Winkler K Lerch EI Solomon 1981 J Am Chem Soc 103 7001 7003