Quantum chemical studies for oxidation of morpholine by Cytochrome P450

Journal of Inorganic Biochemistry

Volumn 103, Issue 1, 2009, Pages 20-27

  Shaikh, Abdul Rajjak ^a   Sahnoun, Riadh ^a   Broclawik, Ewa ^b   Koyama, Michihisa ^a   Tsuboi, Hideyuki ^a   Hatakeyama, Nozomu ^a   Endou, Akira ^a   Takaba, Hiromitsu ^a   Kubo, Momoji ^a   Carpio, Carlos A Del ^a   Miyamoto, Akira ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b INSTITUTE OF CATALYSIS AND SURFACE CHEMISTRY   (Poland)

Author keywords

Cytochrome P450; DFT modeling; Enzymatic oxidation; Morpholine biodegradation

Indexed keywords

2 (2 AMINOETHOXY)ACETALDEHYDE; ACETALDEHYDE; CYTOCHROME P450; IRON COMPLEX; MORPHOLINE; NITROGEN; OXYGEN; PORPHYRIN; UNCLASSIFIED DRUG; WATER;

ARTICLE; BIODEGRADATION; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENZYME ACTIVE SITE; HYDROXYLATION; OXIDATION; QUANTUM CHEMISTRY;

CATALYTIC DOMAIN; CYTOCHROME P-450 ENZYME SYSTEM; MORPHOLINES; OXIDATION-REDUCTION; QUANTUM THEORY;

EID: 56649111217     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2008.08.013     Document Type: Article

References (56)

1. Lewis Sr. R.J. Danger Prop. Ind. Mater. Rep. 15 (1995) 270-297
2. Enzmann H., Zerban H., Kopp-Schneider A., Loser E., and Bannasch P. Carcinogenesis 16 (1995) 1513-1518
3. Cech J.S., Hartman P., Slosárek M., and Chudoba J. Appl. Environ. Microbiol. 54 (1988) 619-621
4. Dmitrenko G.N., and Gvozdyak P.I. Proceedings of Conference on Microbiological Methods for Protecting the Environment (1988), Centre for Biological Research, Puschino, USSR
5. Knapp J.S., Callely A.G., and Mainprize J.J. Appl. Bacteriol. 52 (1982) 5-13
6. Knapp J.S., and Brown V.R. Int. Biodeterior. Bull. 24 (1988) 299-306
7. Mazure N., and Truffaut N. Can. J. Microbiol. 40 (1994) 761-765
8. Poupin P., Truffaut N., Combourieu B., Besse P., Sancelme M., Veschambre H., and Delort A.M. Appl. Environ. Microbiol. 64 (1998) 159-165
9. Dmitrenko G.N., Gvozdyak P.I., and Udod V.M. Khim. Tekhnol. Vody. 9 (1987) 442-445
10. Knapp J.S., Emtiazi G., Yusoff S., and Heron S.T. Lett. Appl. Microbiol. 23 (1996) 334-338
11. Swain A., Waterhouse K.V., Venables W.A., Callely A.G., and Lowe S.E. Appl. Microbiol. Biotechnol. 35 (1991) 110-114
12. Combourieu A., Besse P., Sancelme M., Veschambre H., Delort A.M., Poupin P., and Truffaut N. Appl. Environ. Microbiol. 64 (1998) 153-158
13. Combourieu A., Poupin P., Besse P., Sancelme M., Veschambre H., Truffaut N., and Delort A.M. Biodegradation 9 (1998) 433-442
14. Besse P., Combourieu B., Poupin P., Sancelme M., Truffaut N., Veschambre H., and Delort A.M. J. Mol. Biocatal. B Enz. 5 (1998) 403-409
15. Sielaff B., Andreesen J.R., and Schrader T. Appl. Microbiol. Biotechnol. 56 (2001) 458-464
16. Sielaff B., and Andreesen J.R. Microbiology 151 (2005) 2593-2603
17. Ortiz de Montellano P.R. Cytochrome P450 Structure, Mechanism, and Biochemistry. second ed. (1995), Plenum, New York
18. Nelson D.R., Koymans L., Kamataki T., Stegeman J.J., Feyereisen R., Waxman D.J., Waterman M.R., Gotoh O., Coon M.J., Estabrook R.W., Gunsalus I.C., and Nebert D.W. Pharmacogenetics 6 (1996) 1-42
19. Urlacher V.B., Lutz-Wahl S., and Schmid R.D. Appl. Microbiol. Biotechnol. 64 (2004) 317-325
20. Munro A.W., and Lindsay J.G. Mol. Microbiol. 20 (1996) 1115-1125
21. Guengerich F.P., and Macdonald T.L. FASEB J. 4 (1990) 2453-2459
22. Guengerich F.P., and Macdonald T.L. Adv. Electron Transfer Chem. 3 (1993) 191-241
23. Karki S.B., and Dinnocenzo J.P. Xenobiotica 25 (1995) 711-7124
24. Wang Y., Kumar D., Yang C., Han K., and Shaik S. J. Phys. Chem. B 111 (2007) 7700-7710
25. Ismael M., Del Carpio C.A., Shaikh A.R., Tsuboi H., Koyama M., Hatakeyama N., Endou A., Takaba H., Kubo M., Broclawik E., and Miyamoto A. Mater. Trans. 48 (2007) 730-734
26. Jurva U., Bissel P., Isin E.M., Igarashi K., Kuttab S., and Castagnoli N. J. Am. Chem. Soc. 127 (2005) 12368-12377
27. Hawkins C.L., and Davies M.J. Biochim. Biophys. Acta 1504 (2001) 196-219
28. Sun X., Harder J., Krook M., Jornvall H., Sjoberg B.M., and Reichard P. Proc. Natl. Acad. Sci. USA 90 (1993) 577-588
29. Mulliez E., Fontecave M., Gaillard J., and Reichard P. J. Biol. Chem. 268 (1993) 2296-2299
30. Sun X., Eliasson R., Pontis E., Andersson J., Buist G., Sjoberg B.M., and Reichard P. J. Biol. Chem. 270 (1995) 2443-2446
31. Jordan A., and Reichard P. Annu. Rev. Biochem. 67 (1998) 71-98
32. Knappe J., Neugebauer F.A., Blaschkowski H.P., and Ganzler M. Proc. Natl. Acad. Sci. USA 81 (1984) 1332-1335
33. Parast C.V., Wong K.K., Lewisch S.A., Kozarich J.W., Peisach J., and Magliozzo R.S. Biochemistry 34 (1995) 2393-2399
34. Sono M., Roach M.P., Coulter E.D., and Dawson J.H. Chem. Rev. 96 (1996) 2841-2888
35. Denisov I.G., Makris T.M., Sligar S.G., and Schlichting I. Chem. Rev. 105 (2005) 2253-2278
36. Shaik S., Kumar D., de Visser S.P., Altun A., and Thiel W. Chem. Rev. 105 (2005) 2279-2328
37. Ortiz P.R., de Montellano J.J., and Voss D. Nat. Prod. Rep. 19 (2002) 477-493
38. Klamt A., and Schüürmann G. J. Chem. Soc. Perkin Trans. 2 (1993) 799-805
39. Klamt A., Jonas V., Bürger T., and Lohrenz J. J. Phys. Chem. A 102 (1998) 5074-5085
40. Delley B. J. Chem. Phys. 92 (1990) 508-517
41. Delley B. J. Chem. Phys. 113 (2000) 7756-7764
42. Shaikh A.R., Broclawik E., Ismael M., Tsuboi H., Koyama M., Kubo M., Del Carpio C.A., and Miyamoto A. Chem. Phys. Lett. 419 (2006) 523-527
43. Shaikh A.R., Broclawik E., Ismael M., Tsuboi H., Koyama M., Endou A., Takaba H., Kubo M., Del Carpio C.A., and Miyamoto A. J. Mol. Mod. 13 (2007) 851-860
44. Shaikh A.R., Del Carpio C.A., Tsuboi H., Koyama M., Hatakeyama N., Endou A., Takaba H., Kubo M., and Miyamoto A. A. Mater. Trans. 48 (2007) 740-744
45. Vosko S.J., Wilk L., and Nusair M. Can. J. Phys. 58 (1980) 1200-1211
46. Perdew J.P., and Wang Y. Phys. Rev. B 45 (1992) 13244-13249
47. Siegbahn P.E.M., and Blomberg M.A.A. Annu. Rev. Phys. Chem. 50 (1999) 221-249
48. Lundberg M., and Siegbahn P.E.M. J. Comput. Chem. 26 (2005) 661-667
49. Radon M., and Broclawik E. J. Chem. Theory Comput. 3 (2007) 728-734
50. Hammes-Schiffer S., Hatcher E., Ishikita H., Skone J.H., and Soudackov A.V. Coord. Chem. Rev. 252 (2008) 384-394
51. Groves J.T., and McClusky G.A. J. Am. Chem. Soc. 98 (1976) 859-861
52. Groves J.T. J. Chem. Educ. 62 (1985) 928-931
53. Vidakovic M., Sligar S.G., Li H., and Poulos T.L. Biochemistry 37 (1998) 9211-9219
54. Weiner S.J., Singh U.C., and Kollman P.A. J. Am. Chem. Soc. 107 (1985) 2219-2229
55. Antonczak S., Ruiz-Lopez M.F., and Rivail J.L. J. Am. Chem. Soc. 116 (1994) 3912-3921
56. Bakowies D., and Kollman P.A. J. Am. Chem. Soc. 121 (1999) 5712-5726