The catalytic cycle of tyrosinase: Peroxide attack on the phenolate ring followed by O-O bond cleavage

Journal of Biological Inorganic Chemistry

Volumn 8, Issue 5, 2003, Pages 567-576

  Siegbahn, Per E M ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Copper; Density functional theory; Geometry optimizations; Phenols; Tyrosinase

Indexed keywords

COORDINATION COMPOUND; COPPER DERIVATIVE; HISTIDINE DERIVATIVE; LIGAND; MONOPHENOL MONOOXYGENASE; OXYGEN; PEROXIDE; PHENOL DERIVATIVE; WATER;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME MECHANISM; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS;

LYCAENINAE;

EID: 0037496170     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-003-0449-4     Document Type: Article

References (52)

1. Solomon EI, Sundaram UM, Machonkin TE (1996) Chem Rev 96:2563-2605
2. Kitajima M, Moro-Oka Y (1994) Chem Rev 94:737-757
3. Lerch K (1994) In: King RB (ed) Encyclopedia of inorganic chemistry. Wiley, Chichester, pp 850-869
4. Halcrow MA, Knowles PF, Phillips SEV (2001) In: Bertini I, Sigel H (eds) Handbook on metalloproteins. Dekker, New York, pp 709-762
5. Eicken C, Gerdemann C, Krebs B (2001) In: Messerschmidt A, Huber R, Poulus T, Wieghardt K (eds) Handbook of metalloproteins. Wiley, Chichester, pp 1319-1329
6. Rodriguez-Lopez JN, Tudela J, Varon R, Garcia-Carmona F, Garcia-Canovas F (1992) J Biol Chem 267:3801-3810
7. Volbeda A, Hol WG (1989) J Mol Biol 209:249-279
8. Magnus KA, Hazes B, Ton-That H, Bonaventura C, Bonaventura J, Hol WG (1994) Proteins Struct Funct Genet 19:302-309
9. Klabunde T, Eicken C, Saccettini JC, Krebs B (1998) Nat Struct Biol 5:1084-1090
10. Decker H, Rimke T (1998) J Biol Chem 273:25889-25892
11. Espin JC, Morales M, Varon R, Tudela J, Garcia-Canovas F (1997) Phytochemistry 44:17-22
12. Espin JC, Ochoa M, Tudela J, Garcia-Canovas F (1997) Phytochemistry 45:667-670
13. Halfen JA, Mahapatra S, Wilkinson EC, Kaderli S, Que L, Tolman WB (1996) Science 271:1397-1400
14. Tolman WB (1997) Acc Chem Res 30:227-237
15. Mahadevan V, Henson MJ, Solomon EI, Stack TDP (2000) J Am Chem Soc 122:10249-10250
16. Que L Jr, Tolman WB (2002) Angew Chem Int Ed 41:1114-1137
17. Liang H-C, Zhang CX, Henson MJ, Sommer RD, Hatwell KR, Kaderli S, Zuberbühler AD, Rheingold AL, Solomon EI, Karlin KD (2002) J Am Chem Soc 124:4170-4171
18. Sayre LM, Nadkarni DV (1994) J Am Chem Soc 116:3157-3158
19. Mandal S, Macikenas D, Protasiewicz JD, Sayre LM (2000) J Org Chem 65:4804-4809
20. Bernardi F, Bottoni A, Casadio R, Fariselli P, Rigo A (1996) Inorg Chem 35:5207-5212
21. Mahapatra S, Halfen JA, Wilkinson EC, Pan G, Wang X, Young VG Jr, Cramer CJ, Que L Jr, Tolman WB (1996) J Am Chem Soc 118:11555-11574
22. Bërces A (1997) Inorg Chem 36:4831-4837
23. Lind T, Siegbahn PEM, Crabtree RH (1999) J Phys Chem 103:1193-1202
24. Flock M, Pierloot K (1999) J Phys Chem A 103:95-102
25. Lam BMT, Halfen JA, Young VG Jr, Hagadorn JR, Holland PL, Ledos A, Cucurull-Sanchez L, Novoa JJ, Alvarez S, Tolman WB (2000) Inorg Chem 39:4059-4072
26. Siegbahn PEM, Wirstam M (2001) J Am Chem Soc 123:11819-11820
27. Pierloot K (2001) In: Cundari TR (ed) Computational organometallic chemistry. Dekker, New York, pp 123-158
28. Pierloot K (2003) Mol Phys (in press)
29. Siegbahn PEM (2003) J Biol Inorg Chem (in press)
30. Siegbahn PEM (2001) J Comput Chem 22:1634-1645
31. Siegbahn PEM (1999) Inorg Chem 38:2880-2889
32. Metz M, Solomon EI (2001) J Am Chem Soc 123:4938-4950
33. Siegbahn PEM, Blomberg MRA (2000) Chem Rev 100:421-437
34. Siegbahn PEM, Blomberg MRA (2001) J Phys Chem B 105:9375-9386
35. Siegbahn PEM (2003) Q Rev Biophys 36:91-145
36. Becke AD (1988) Phys Rev A 38:3098-3100
37. Becke AD (1993) J Chem Phys 98:1372-1377
38. Becke AD (1993) J Chem Phys 98:5648-5652
39. Hay PJ, Wadt WR (1985) J Chem Phys 82:299-310
40. Blomberg MRA, Siegbahn PEM, Babcock GT (1998) J Am Chem Soc 120:8812-8824
41. Kuramochi H, Noodleman L, Case DA (1997) J Am Chem Soc 119:11442-11451
42. Mouesca J-M, Chen JL, Noodleman L, Bashford D, Case DA (1994) J Am Chem Soc 116:11898-11914
43. Li J, Nelson MR, Peng CY, Bashford D, Noodleman L (1998) J Phys Chem A 102:6311-6324
44. Li J, Fisher CL, Konecny R, Bashford D, Noodleman L (1999) Inorg Chem 39:929-939
45. Konecny R, Li J, Fisher CL, Dillet V, Bashford D, Noodleman L (1999) Inorg Chem 39:940-950
46. Noodleman L, Li J, Zhao X-G, Richardson WH (1997) In: Springborg M (ed) Methods in chemistry and materials science. Wiley, New York, pp 149-187
47. Zhao XG, Richardson WH, Chen JL, Li J, Noodleman L, Tsai H-L, Hendrickson DN (1997) Inorg Chem 36:1198-1217
48. Schrödinger (1991-2000) Jaguar 4.0. Schrödinger, Portland, Ore., USA
49. Itoh S, Kumei H, Taki M, Nagatomo S, Kitagawa T, Fukuzumi S (2001) J Am Chem Soc 123:6708-6709
50. Curtiss LA, Raghavachari K, Pople JA (1993) J Chem Phys 98:1293-1298
51. Froese DJ, Humbel S, Svensson M, Morokuma K (1997) J Phys Chem 101:227-233
52. Curtiss LA, Raghavachari K, Redfern RC, Pople JA (2000) J Chem Phys 112:7374-7383