Systematic study on the mechanism of aldehyde oxidation to carboxylic acid by cytochrome P450

Journal of Biological Inorganic Chemistry

Volumn 12, Issue 7, 2007, Pages 1073-1081

  Liu, Xiaojing ^a   Wang, Yong ^a   Han, Keli ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Aldehyde; Compound I; Hydroxylation; P450

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID; CYTOCHROME P450; HYDROGEN; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL;

ALDEHYDES; CARBOXYLIC ACIDS; COMPUTER SIMULATION; CYTOCHROME P-450 ENZYME SYSTEM; FORMALDEHYDE; HYDROXYLATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 34548451620     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-007-0277-z     Document Type: Article

References (58)

1. Rendic S (2002) Drug Metab Rev 34:83-448
2. Guengerich FP (2001) Curr Drug Metab 2:93-115
3. Kumar D, de Visser SP, Sharma PK, Derat E, Shaik S (2005) J Biol Inorg Chem 10:181-189
4. Ortiz de Montellano PR (ed) (1995) CytochromeP450: structure, mechanism and biochemistry, 2nd edn. Plenum, New York
5. Shaik S, Kumar D, de Visser SP, Altun A, Thiel W (2005) Chem Rev 105:2279-2328
6. Nam W, Ryu YO, Song WJ (2004) J Biol Inorg Chem 9:654-660
7. Shaik S, de Visser SP, Kumar D (2004) J Biol Inorg Chem 9:661-668
8. Harris N, Cohen S, Filatov M, Ogliaro F, Shaik S (2000) Angew Chem Int Ed Engl 39:2003-2007
9. De Visser SP, Shaik S (2003) J Am Chem Soc 125:7413-7424
10. Ogliaro F, Harris N, Cohen S, Filatov M, de Visser SP, Shaik S (2000) J Am Chem Soc 122:8977-8989
11. Kumar D, de Visser SP, Sharma PK, Cohen S, Shaik S (2004) J Am Chem Soc 126:1907-1920
12. De Visser SP, Ogliaro F, Sharma PK, Shaik S (2002) J Am Chem Soc 124:11809-11826
13. Kumar D, de Visser SP, Shaik S (2003) J Am Chem Soc 125:13024-13025
14. De Visser SP, Ogliaro F, Shaik S (2001) Angew Chem Int Ed Engl 40:2871-2874
15. Li C, Wu W, Kumar D, Shaik S (2006) J Am Chem Soc 128:394-395
16. Kamachi T, Yoshizawa K (2003) J Am Chem Soc 125:4652-4661
17. Wang Y, Wang HM, Wang YH, Yang CL, Yang L, Han KL (2006) J Phys Chem B 110:6154-6159
18. Groves JT, McClusky GA (1976) J Am Chem Soc 98:859-861
19. Ogliaro F, Filatov M, Shaik S (2000) Eur J Inorg Chem 2000:2455-2458
20. De visser SP, Ogliaro F, Sharma PK, Shaik S (2002) Angew Chem Int Ed Engl 41:1947-1951
21. Guallar V, Friesner RA (2004) J Am Chem Soc 126:8501-8508
22. Shaik S, Cohen S, de Visser SP, Sharma PK, Kumar D, Kozuch S, Ogliaro F, Danovich D (2004) Eur J Inorg Chem 207-226
23. De Visser SP, Kumar D, Cohen S, Shacham R, Shaik S (2004) J Am Chem Soc 126:8362-8363
24. Shaik S, Shurki A (1999) Angew Chem Int Ed Engl 38:586-625
25. Watanabe K, Narimatsu S, Yamamoto I, Yoshimura H (1990) Biochem Biophys Res Commun 166:1308-1312
26. Watanabe K, Narimatsu S, Yamamoto I, Yoshimura H (1991) J Biol Chem 266:2709-2711
27. Robert ES, Vaz ADN, Coon MJ (1992) Mol Pharmacol 41:427-433
28. Watanabe K, Matsunaga T, Narimatsu S, Yamamoto I, Yoshimura H (1992) Biochem Biophys Res Commun 188:114-119
29. Vaz ADN, Kessell KJ, Coon MJ (1994) Biochemistry 33:13651-13661
30. Davis SC, Sui Z, Peterson JA, Ortiz de Montellano PR (1996) Arch Biochem Biophys 328:35-42
31. Raner GM, Vaz ADN, Coon MJ (1996) Mol Pharmacol 49:515-522
32. Raner GM, Chiang EW, Vaz ADN, Coon MJ (1997) Biochemistry 36:4895-4902
33. Bell-Parikh LC, Guengerich FP (1999) J Bio Chem 274:23833-23840
34. Shaik S, de Visser SP, Ogliaro F, Schwarz H, Schröder D (2002) Curr Opin Chem Biol 6:556-567
35. Shaik S, Filatov M, Schröder D, Schwarz H (1998) Chem Eur J 4:193-199
36. Schröder D, Shaik S, Schwarz H (2000) Acc Chem Res 33:139-145
37. Mayer JM (1998) Acc Chem Res 31:441-450
38. Kaizer J, Klinker EJ, Oh NY, Rohde JU, Song WJ, Stubna A, Kim J, Münck E, Nam W, Que L Jr (2004) J Am Chem Soc 126:472-473
39. Park JY, Harris D (2003) J Med Chem 46:1645-1660
40. Silaghi-Dumitrescu R (2004) J Biol Inorg Chem 9:471-476
41. Kumar D, de Visser SP, Sharma PK, Hirao H, Shaik S (2005) Biochemistry 44:8148-8158
42. Kumar D, Hirao H, de Visser SP, Zheng JJ, Wang DQ, Thiel W, Shaik S (2005) J Phys Chem B 109:19946-19951
43. Kumar D, de Visser SP, Shaik S (2004) J Am Chem Soc 126:5072-5073
44. Kamachi T, Yoshizawa K (2005) J Am Chem Soc 127:10686-10692
45. Yoshizawa K, Kamachi T, Shiota Y, (2001) J Am Chem Soc 123:9806-9816
46. Yoshizawa K, Kagawa Y, Shiota Y, (2000) J Phys Chem B 104:12365-12370
47. Watanabe Y (2001) J Biol Inorg Chem 6:846-856
48. Song WJ, Ryu YO, Song R, Nam W (2005) J Biol Inorg Chem 10:294-304
49. Lee C, Yang W, Parr RG, (1988) Phys Rev B 37:785-789
50. Becke AD (1993) J Chem Phys 98:1372-1377
51. Becke AD (1988) Phys Rev A 38:3098-3100
52. 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 VG, 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 (2004) Gaussian 03, revision C, 02 edn. Gaussian, Wallingford
53. Dunning TH, Hay PJ (1976) In: Schaefer HF (ed) Modern theoretical chemistry. Plenum, New York
54. Friesner RA, Murphy RB, Beachy MD, Ringnalda MN, Pollard WT, Dunietz BD, Cao YX (1999) J Phys Chem A 103:1913-1928
55. Borden WT (1975) Modern molecular orbital theory for organic chemists. Prentice Hall, Englewood Cliffs
56. Fleming I (1982) Frontier orbitals and organic chemical reactions. Wiley, London
57. Schöneboom JC, Cohen S, Lin H, Shaik S, Thiel W (2004) J Am Chem Soc 126:4017-4034
58. Vaz ADN, Coon MJ (1994) Biochemistry 33:6442-6449