Enzymatic activation of alkanes: Constraints and prospective

Applied Catalysis A: General

Volumn 272, Issue 1-2, 2004, Pages 1-13

  Ayala, Marcela ^a   Torres, Eduardo ^a  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

Alkane activation; Biocatalysis; Enzyme; Hydroxylase; Monooxygenase; Reaction mechanism

Indexed keywords

ACTIVATION ENERGY; ALCOHOLS; BIOCATALYSTS; CATALYSIS; CHEMICAL BONDS; ELECTRON TRANSITIONS; ENZYMES; METHANE; RAW MATERIALS; REACTION KINETICS;

ALKANE ACTIVATION; HYDROXYLASE; MONOOXYGENASE;

PARAFFINS;

EID: 3843128486     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2004.05.046     Document Type: Review

References (111)

1. C. Boswell, The Technology Frontier: Alkane Activation, Chemical Market Reporter, New York, 1999 (Dic. 20).
2. Chem Systems, Alkane Activation: Petrochemical Feedstocks of the Future, 1999.
3. Labinger J.A., Bercaw J.E. Nature. 417:2002;507.
4. I.M. Clegg, R. Hardman, US Patent 5,728,905 (1998), EVC Technology AG.
5. H. Borchert, U. Dingerdissen, R. Roesky, US Patent 6,274,765 (2001), Hoechst Research and Technology Deutschland GmbH and Co.
6. K. Karim, M.H. Al-Hazmi, A.A. Khan, S.I. Zaherr, US Patent 6,531,631 (2003), Saudi Basic Industries Co.
7. H. Jachow, A. Tenten, S. Unverricht, H. Arnold, US Patent 6,541,664 (2003), BASF Asktienjessellschaft.
8. OECD, The Application of Biotechnology to Industrial Sustainability, 2001. http://www.oecd.org/sti/biotechnology.
9. Schoemaker H.E., Mink D., Wubbolts H.G. Science. 299:2003;1694.
10. van Beilen J.B., Duetz W.A., Schmid A., Witholt B. Trends Biotechnol. 21:2003;170.
11. Lange S.J., Que L. Curr. Opin. Chem. Biol. 2:1998;159.
12. Westerheide L., Pascaly M., Krebs B. Curr. Opin. Chem. Biol. 4:2000;235.
13. Straathof A.J.J., Panke S., Schmid A. Curr. Opin. Biotechnol. 13:2002;548.
14. G. DeSantis, Modern Drug Discovery, August 2002, p. 43.
15. EC enzyme classification page. http://65.219.84.5/prowl/aainfo/enzymes/ enzymes.htm.
16. Intelligence Report, Business shift in the global catalyst industry 2001-2007, The Catalyst Group Resource Inc., April 2002.
17. Koeller K.M., Wong C.H. Nat. Biotechnol. 409:2001;232.
18. Krishna S.H. Biotechnol. Adv. 20:2002;239.
19. Patel R.N. Enzyme Microbiol. Technol. 31:2002;804.
20. Huisman G.W., Gray D. Curr. Opin. Biotechnol. 13:2002;352.
21. Schmid A., Hollmann F., Park J.B., Bühler B. Curr. Opin. Biotechnol. 13:2002;359.
22. Rozzell J.D. Bioorg. Med. Chem. 7:1999;2253.
23. Schiraldi C., De Rosa M. Trends Biotechnol. 20:2002;515.
24. van den Burg B. Curr. Opin. Microbiol. 6:2003;213.
25. M.T. Madigan, B.L. Marrs, Sci. Am. (April 1997) 66.
26. Salanitro J.P. Adv. Agron. 72:2001;53.
27. Arp D.J. Microbiology. 145:1999;1173.
28. Smits T.H.M., Balada S.B., Witholt B., van Beilen J.B. J. Bacteriol. 184:2002;1733.
29. Gallo M., Bertrand J.C., Roche B., Azoulay E. Biochim. Biophys. Acta. 296:1973;624.
30. Brenda: The Comprehensive Enzyme Information System. http://www.brenda. uni-koeln.de.
31. Murrell J.C., Gilbert B., McDonald I.R. Arch. Microbiol. 173:2000;325.
32. Nguyen H.T., Elliot S.J., Yip J.H., Chan S.L. J. Biol. Chem. 273:1998;7957.
33. Murrell J.C., McDonald I.R., Gilbert B. Trends Microbiol. 8:2000;221.
34. Elliot S.J., Zhu M., Tso L., Nguyen H.T., Yip J.H., Chan S.I. J. Am. Chem. Soc. 119:1997;9949.
35. Green J., Dalton H. J. Biol. Chem. 264:1989;17698.
36. Choi D.W., Kunz R.C., Boyd E.S., Semrau J.D., Antholine W.E., Han J.I., Zahn J.A., Boyd J.M., de la Mora A.M., DiSpirito A.A. J. Bacteriol. 185:2003;5755.
37. Basu P., Katterle B., Andersson K.K., Dalton H. Biochem. J. 369:2003;417.
38. Fox B.G., Froland W.A., Dege J.E., Lipscombs J.D. J. Biol. Chem. 264:1989;10023.
39. Shanklin J., Achim C., Schmid H., Fox B.G., Münck E. Proc. Natl. Acad. Sci. USA. 94:1997;2981.
40. Schmid A., Sonnleitner B., Witholt B. Biotechnol. Bioeng. 60:1998;10.
41. Ratajczak A., Geißdörfer W., Hillen W. J. Bacteriol. 180:1998;5822.
42. Whyte L.G., Smits T.H.M., Labbé D., Witholt B., Greer C.W., van Beilen J.B. Appl. Environ. Microbiol. 68:2002;5933.
43. Tani A., Ishige T., Sakai Y., Kato N. J. Bacteriol. 183:2001;1819.
44. Marin N.N., Yuste L., Rojo F. J. Bacteriol. 185:2003;3232.
45. Leahy J.G., Batchelor P.J., Morcomb S.M. FEMS Microbiol. Rev. 27:2003;449.
46. Shanklin J., Whittle E., Fox B.G. Biochemistry. 33:1994;12787.
47. Shanklin J., Whittle E. FEBS Lett. 545:2003;188.
48. van Beilen J.B., Wubbolts M.G., Witholt B. Biodegradation. 5:1994;161.
49. Bosetti A., van Beilen J.B., Preusting H., Lageveen R.G., Witholt B. Enzyme Microbiol. Technol. 14:1992;702.
50. Rothen S.A., Sauer M., Sonnleitner B., Witholt B. Biotechnol. Bioeng. 58:1998;356.
51. Appel D., Lutz-Wahl S., Fischer P., Schwaneberg U., Schmid R.D. J. Biotechnol. 88:2001;167.
52. Stevenson J.A., Westlake A.C.G., Whittock C., Wong L.L. J. Am. Chem. Soc. 118:1996;12846.
53. Zimmer T., Ohkuma M., Ohta A., Takagi M., Schunck W.H. Biochem. Biophys. Res. Commun. 224:1996;784.
54. Zimmer T., Iida T., Schunck W.H., Yoshida Y., Ohta A., Takagi M. Biochem. Biophys. Res. Commun. 251:1998;244.
55. Yadav J.S., Loper J.C. Gene. 226:1999;139.
56. Sono M., Roach M.P., Coulter E.D., Dawson J.H. Chem. Rev. 96:1996;2841.
57. Hill F.F., Venn I., Lukas K.L. Appl. Microbiol. Biotechnol. 24:1986;168.
58. S. Picataggio, T. Rohrer, L.D. Eirich, US Patent 5,648,247 (1997), Henkel Corporation.
59. Craft D.L., Madduri K.M., Eshoo M., Wilson C.R. Appl. Environ. Microbiol. 69:2003;5983.
60. Eschenfeldt W.H., Zhang Y., Samaha H., Stols L., Eirich L.D., Wilson C.R., Donnelly M.I. Appl. Environ. Microbiol. 69:2003;5992.
61. Picataggio S., Rohrer T., Deanda K., Lanning D., Reynolds R., Mielenz J., Eirich L.D. Biotechnology. 10:1992;894.
62. Peters M.W., Meinhold P., Glieder A., Arnold F.H. J. Am. Chem. Soc. 125:2003;13442.
63. Glieder A., Farinas E.T., Arnold F.H. Nat. Biotechnol. 20:2002;1135.
64. Wallar B.J., Lipscomb J.D. Chem. Rev. 96:1996;2625.
65. Baik M.H., Newcomb M., Friesner R.A., Lippard S.J. Chem. Rev. 103:2003;2385.
66. Tshuva E.Y., Lippard S.J. Chem. Rev. 104:2004;987.
67. Liu Y., Nesheim J.C., Lee S.K., Lipscomb J.D. J. Biol. Chem. 270:1995;24662.
68. Lee S.K., Lipscomb J.D. Biochemistry. 38:1999;4423.
69. Brazeau B.J., Lipscomb J.D. Biochemistry. 39:2000;13503.
70. Lee S.K., Nesheim J.C., Lipscomb J.D. J. Biol. Chem. 268:1993;21569.
71. Liu K.E., Valentine A.M., Wang D.L., Huynh B.H., Edmondson D.E., Salifoglou A., Lippard S.J. J. Am. Chem. Soc. 117:1995;10174.
72. Lee S.K., Fox B.G., Froland W.A., Lipscomb J.D., Munck E. J. Am. Chem. Soc. 115:1993;6450.
73. Shu L., Nesheim J.C., Kauffmann K., Münck E., Lipscomb J.D., Que L. Jr. Science. 275:1997;515.
74. Kim K., Lippard S.J. J. Am. Chem. Soc. 118:1996;4914.
75. Dawson J.H. Science. 240:1988;433.
76. Nesheim J.C., Lipscomb J.D. Biochemistry. 35:1996;10240.
77. Lipscomb J.D., Que L. J. Biol. Inorg. Chem. 3:1998;331.
78. Whittington D.A., Valentine A.M., Lippard S.J. J. Biol. Inorg. Chem. 3:1998;307.
79. Deeth R.J., Dalton H. J. Biol. Inorg. Chem. 3:1998;302.
80. Choi S.Y., Eaton P.E., Kopp D.A., Lippard S.J., Newcomb M., Shen R. J. Am. Chem. Soc. 121:1999;12198.
81. Valentine A.M., Stahl S.S., Lippard S.J. J. Am. Chem. Soc. 121:1999;3876.
82. Fox B.G., Borneman J.G., Wackett L.P., Lipscomb J.D. Biochemistry. 29:1990;6419.
83. Jin Y., Lipscomb J.D. J. Biol. Inorg. Chem. 6:2001;717.
84. Valentine A.M., Wilkinson B., Liu K.E., Komarpanicucci S., Priestley N.D., Williams P.G., Morimoto H., Floss H.G., Lippard S.J. J. Am. Chem. Soc. 119:1997;1818.
85. Brazeau B.J., Austin R.N., Tarr C., Groves J.T., Lipscomb J.D. J. Am. Chem. Soc. 123:2001;11831.
86. P.R. Ortiz de Montellano (Ed.), Cytochrome P-450: Structure, Mechanisms and Biochemistry, 2nd ed., Plenum Press, New York, 1995.
87. Guengerich F.P. Chem. Res. Toxicol. 3:1990;363.
88. F.P. Guengerich, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450: Structure, Mechanism, Biochemistry, Plenum Press, New York, 1995.
89. Abel S.M., Back D.J. J. Steroid Biochem. Mol. Biol. 46:1993;827.
90. Waxman D.J., Attisano C., Guengerich F.P., Lapenson D.P. Arch. Biochem. Biophys. 263:1988;424.
91. Kerlan V., Dreano Y., Bercovici J.P., Beaune P.H., Floch H.H., Berthou F. Biochem. Pharmacol. 3:1992;1745.
92. Yamazaki H., Shimada T. Arch. Biochem. Biophys. 346:1997;161.
93. Lewis D.F.V., Watson E., Lake B.G. Mutat. Res. 410:1998;242.
94. H.G. Muller, W.H. Schunck, E. Kargel, in: H. Rein, K. Ruckpaul (Ed.), Frontiers of Biotransformation, vol. 4, Taylor & Francis, London, 1991.
95. Hjelmeland L.M., Aronow L., Trudell J.R. Biochem. Biophys. Res. Commun. 76:1977;541.
96. White R.E., Miller J.P., Favreau L.V., Bhattacharyaa A. J. Am. Chem. Soc. 108:1986;6024.
97. Newcomb M., Shen R., Choi S.Y., Toy P.H., Hollenberg P.F., Vaz A.D.N., Coon M.J. J. Am. Chem. Soc. 122:2000;2677.
98. Duetz W.A., van Beilen J.B., Witholt B. Curr. Opin. Biotechnol. 12:2001;419.
99. Maeng J.H., Sakai Y., Tani Y., Kato N. J. Bacteriol. 178:1996;3695.
100. Hamamura N., Yeager C.M., Aro D.J. Appl. Environ. Microbiol. 67:2001;4992.
101. Sluis M.K., Sayavedra-Soto L.A., Arp D.J. Microbiology. 148:2002;3617.
102. Cheng Q., Thomas S.M., Rouviere P. Appl. Microbiol. Biotechnol. 58:2002;704.
103. Jayaraman A., Yarmush M.L., Roth C.M. Ind. Eng. Chem. Res. 41:2002;441.
104. Farinas E.T., Butler T., Arnold F.H. Curr. Opin. Biotechnol. 12:2001;545.
105. Cirini P.C., Arnold F.H. Curr. Opin. Chem. Biol. 6:2002;130.
106. Smith T.J., Slade S.E., Burton N.P., Murrell J.C., Dalton H. Appl. Environ. Microbiol. 68:2002;5265.
107. Urlacher V., Schmid R.D. Curr. Opin. Biotechnol. 13:2002;557.
108. Zhao H., van der Donk W.A. Curr. Opin. Biotechnol. 14:2003;583.
109. Tishkov V.I., Galkin A.G., Fedorchuk V.V., Savitsky P.A., Rojkova A.M., Gieren H., Kula M.R. Biotechnol. Bioeng. 64:1999;187.
110. Mertens R., Greiner L., van den Ban E.C.D., Haaker H.B.C.M., Liese A. J. Mol. Catal. B: Enzym. 24-25:2003;39.
111. Mathys R.G., Schmid A., Witholt B. Biotechnol. Bioeng. 64:1999;459.