Biocatalytic conversion of avermectin into 4″-oxo-avermectin: Discovery, characterization, heterologous expression and specificity improvement of the cytochrome P450 enzyme

Biochemical Society Transactions

Volumn 34, Issue 6, 2006, Pages 1236-1240

  Molnar I ^a,d   Jungmann, V ^b   Stege, J ^c   Trefzer, A ^c,e   Pachlatko, J P ^b  

^a SYNGENTA BIOTECHNOLOGY INC   (United States)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

^c DIVERSA CORPORATION   (United States)

^d Environmental Research Laboratory   (United States)

^e INVITROGEN CORPORATION   (United States)

Author keywords

Avermectin; Biocatalysis; Cytochrome P450 mono oxygenase; Emamectin benzoate; Ferredoxin; Gene reassembly

Indexed keywords

4 OXO AVERMECTIN; AVERMECTIN; CYTOCHROME P450; EMAMECTIN BENZOATE; FERREDOXIN; FERREDOXIN NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCTASE; INSECTICIDE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; 4'' OXO AVERMECTIN; 4''-OXO-AVERMECTIN; DRUG DERIVATIVE; IVERMECTIN; SOLVENT;

BIOTRANSFORMATION; CATALYSIS; CONFERENCE PAPER; CONTROLLED STUDY; ELECTRON TRANSPORT; ENZYME KINETICS; ENZYME METABOLISM; ENZYME SPECIFICITY; ESCHERICHIA COLI; GENE IDENTIFICATION; GENE SEQUENCE; HIGH THROUGHPUT SCREENING; MOLECULAR CLONING; NONHUMAN; PRIORITY JOURNAL; PROMOTER REGION; PROTEIN EXPRESSION; PSEUDOMONAS PUTIDA; STREPTOMYCES COELICOLOR; STREPTOMYCES LIVIDANS; ARTICLE; GENETICS; KINETICS; METABOLISM;

ESCHERICHIA COLI; PSEUDOMONAS PUTIDA; STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCES LIVIDANS;

BIOTRANSFORMATION; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; ELECTRON TRANSPORT; IVERMECTIN; KINETICS; SOLVENTS;

EID: 34248655164     PISSN: 03005127     EISSN: None     Source Type: Journal    
DOI: 10.1042/BST0341236     Document Type: Conference Paper

References (35)

1. Schmid, A., Dordick, J.S., Hauer, B., Kiener, A., Wubbolts, M. and Witholt, B. (2001) Nature 409, 258-268
2. Adachi, O., Moonmangmee, D., Toyama, H., Yamada, M., Shinagawa, E. and Matsushita, K. (2003) Appl. Microbiol. Biotechnol. 60, 643-653
3. Morita, M. and Watanabe, Y. (1977) Agric. Biol. Chem. 41, 1535-1537
4. Drauz, K. and Waldmann, H. (1995) Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, vol. II, VCH, Weinheim, Germany
5. Waterman, M.R. and Johnson, E.F. (eds.) (1991) Methods in Enzymology, vol. 206, Academic Press, San Diego
6. Ortiz de Montellano, P.R. (1995) Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd edn, Plenum Press, New York
7. Walczak, R.J., Hines, J.V., Strohl, W.R. and Priestley, N.D. (2001) Org. Lett. 3, 2277-2279
8. Berrie, J.R., Williams, R.A. and Smith, K.E. (1999) J. Steroid Biochem. Mol. Biol. 71, 153-165
9. Taylor, M., Lamb, D.C., Cannell, R., Dawson, M. and Kelly, S.L. (1999) Biochem. Biophys. Res. Commun. 263, 838-842
10. Omer, C.A., Lenstra, R., Little, P.J., Dean, C., Tepperman, J.M., Leto, K.J., Romesser, J.A. and O'Keefe, D.P. (1990) J. Bacteriol. 172, 3335-3345
11. Dejonghe, W., Boon, N., Seghers, D., Top, E.M. and Verstraete, W. (2001) Environ. Microbiol. 3, 649-657
12. Cvetovich, R.J., Kelly, D.H., DiMichele, L.M., Shuman, R.F. and Grabowski, E.J.J. (1994) J. Org. Chem. 59, 7704-7708
13. Molnár, I., Hill, D.S., Zirkle, R., Hammer, P.E., Gross, F., Buckel, T.G., Jungmann, V., Pachlatko, J.P. and Ligon, J.M. (2005) Appl. Environ. Microbiol. 71, 6977-6985
14. Jungmann, V., Molnár, I., Hammer, P.E., Hill, D.S., Zirkle, R., Buckel, T.G., Buckel, D., Ligon, J.M. and Pachlatko, J.P. (2005) Appl. Environ. Microbiol. 71, 6968-6976
15. Lamb, D.C., Skaug, T., Song, H.L., Jackson, C.J., Podust, L.M., Waterman, M.R., Kell, D.B., Kelly, D.E. and Kelly, S.L. (2002) J. Biol. Chem. 277, 24000-24005
16. Bentley, S.D., Chater, K.F., Cerdeno-Tarraga, A.M., Challis, G.L., Thomson, N.R., James, K.D., Harris, D.E., Quail, M.A., Kieser, H., Harper, D. et al. (2002) Nature 417, 141-147
17. Ikeda, H., Ishikawa, J., Hanamoto, A., Shinose, M., Kikuchi, H., Shiba, T., Sakaki, Y., Hattori, M. and Omura, S. (2003) Nat. Biotechnol. 21, 526-531
18. Capdevila, J.H., Wei, S., Helvig, C., Falck, J.R., Belosludtsev, Y., Truan, G., Graham-Lorence, S.E. and Peterson, J.A. (1996) J. Biol. Chem. 271, 22663-22671
19. Shafiee, A. and Hutchinson, C.R. (1987) Biochemistry 26, 6204-6210
20. Andersen, J.F. and Hutchinson, C.R. (1992) J. Bacteriol. 174, 725-735
21. Taylor, M., Lamb, D.C., Cannell, R.J.P., Dawson, M.J. and Kelly, S.L. (2000) Biochem. Biophys. Res. Commun. 279, 708-711
22. Seelbach, K., Riebel, B., Hummel, W., Kula, M.R., Tishkov, V.I., Egorov, A.M., Wandrey, C. and Kragl, U. (1996) Tetrahedron Lett. 37, 1377-1380
23. Baik, S.H., Kang, C., Jeon, II, C. and Yun, S.E. (1999) Biotechnol. Tech. 13, 1-5
24. Bibb, M.J., Janssen, G.R. and Ward, J.M. (1985) Gene 38, E357-E368
25. Murakami, T., Holt, T.G. and Thompson, C.J. (1989) J. Bacteriol. 171, 1459-1466
26. Vieira, J. and Messing, J. (1991) Gene 100, 189-194
27. Panke, S., Meyer, A., Huber, C.M., Witholt, B. and Wubbolts, M.G. (1999) Appl. Environ. Microbiol. 65, 2324-2332
28. Leskiw, B.K., Lawlor, E.J., Fernandez-Abalos, J.M. and Chater, K.F. (1991) Proc. Natl. Acad. Sci. U.S.A. 88, 2461-2465
29. Leskiw, B.K., Bibb, M.J. and Chater, K.F. (1991) Mol. Microbiol. 5, 2861-2867
30. Ali, N., Herron, P.R., Evans, M.C. and Dyson, P.J. (2002) Microbiology 148, 381-390
31. Nelson, K.E., Weinel, C., Paulsen, I.T., Dodson, R.J., Hilbert, H., Martins dos Santos, V.A., Fouts, D.E., Gill, S.R., Pop, M., Holmes, M. et al. (2002) Environ. Microbiol. 4, 799-808
32. O'Keefe, D.P., Gibson, K.J., Emptage, M.H., Lenstra, R., Romesser, J.A., Litle, P.J. and Omer, C.A. (1991) Biochemistry 30, 447-455
33. Lei, L., Waterman, M.R., Fulco, A.J., Kelly, S.L. and Lamb, D.C. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 494-499
34. Sticht, H. (1999) Recent Res. Dev. Biochem. 1, 1-27
35. Weber, F.J., Ooijkaas, L.P., Schemen, R.M.W., Hartmans, S. and de Bont, J.A.M. (1993) Appl. Environ. Microbiol. 59, 3502-3504