Leucine/valine residues direct oxygenation of linoleic acid by (10R)- and (8R)-dioxygenases: Expression and site-directed mutagenesis of (10R)-dioxygenase with epoxyalchohol synthase activity

Journal of Biological Chemistry

Volumn 284, Issue 20, 2009, Pages 13755-13765

  Garscha, Ulrike ^a   Oliw, Ernst H ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERGILLUS FUMIGATUS; CYCLOOXYGENASE; DIOXYGENASE; DIOXYGENASES; INSECT CELLS; LINOLEIC ACID; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; SITE DIRECTED MUTAGENESIS; STEREOSPECIFICITY; SYNTHASE;

ACIDS; AMINO ACIDS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; CHROMATOGRAPHIC ANALYSIS; ENZYMES; ISOMERS; LADDER NETWORKS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MUTAGENESIS; NANOCAPSULES; OLEIC ACID; OXYGENATION; PORPHYRINS;

OXYGENATORS;

10 DIOXYGENASE; 10 HYDROPEROXY 8,12 OCTADECADIENOIC ACID; 7,8 LINOLEATE DIOL SYNTHASE; 8 DIOXYGENASE; 8 HYDROPEROXYLINOLEIC ACID; ALANINE; EPOXYALCOHOL SYNTHASE; FATTY ACID; LEUCINE; LINOLEIC ACID; PHENYLALANINE; PROSTAGLANDIN SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG; VALINE; 8-HYDROPEROXYLINOLEIC ACID; FUNGAL PROTEIN; HYDROPEROXIDE ISOMERASE; ISOMERASE; LIGASE; RECOMBINANT PROTEIN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; ASPERGILLUS FUMIGATUS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME MECHANISM; ENZYME SPECIFICITY; FATTY ACID SYNTHESIS; FUNGUS; GAEUMANNOMYCES GRAMINIS; ISOMER; LIQUID CHROMATOGRAPHY; MUTATION; NONHUMAN; OXYGENATION; PRIORITY JOURNAL; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; SITE DIRECTED MUTAGENESIS; STEREOSPECIFICITY; TANDEM MASS SPECTROMETRY; ANIMAL; BIOSYNTHESIS; CELL LINE; CHEMISTRY; ENZYMOLOGY; GENE EXPRESSION; GENETICS; INSECT; ISOLATION AND PURIFICATION; METABOLISM;

ASPERGILLUS FUMIGATUS; HEXAPODA;

ANIMALS; ASPERGILLUS FUMIGATUS; CELL LINE; FUNGAL PROTEINS; GENE EXPRESSION; INSECTS; INTRAMOLECULAR OXIDOREDUCTASES; LEUCINE; LIGASES; LINOLEIC ACID; LINOLEIC ACIDS; MUTAGENESIS, SITE-DIRECTED; RECOMBINANT PROTEINS; VALINE;

EID: 67649405066     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M808665200     Document Type: Article

References (45)

1. Daiyasu, H., and Toh, H. (2000) J. Mol. Evol. 51, 433-445
2. Su, C., and Oliw, E. H. (1996) J. Biol. Chem. 271, 14112-14118
3. Garscha, U., Jerneren, F., Chung, D., Keller, N. P., Hamberg, M., and Oliw, E. H. (2007) J. Biol. Chem. 282, 34707-34718
4. Tsitsigiannis, D. I., and Keller, N. P. (2006) Mol. Microbiol. 59, 882-892
5. Tsitsigiannis, D. I., Zarnowski, R., and Keller, N. P. (2004) J. Biol. Chem. 279, 11344-11353
6. Dagenais, T. R., Chung, D., Giles, S. S., Hull, C. M., Andes, D., and Keller, N. P. (2008) Infect. Immun. 76, 3214-3220
7. Hamberg, M., Ponce de Leon, I., Rodriguez, M. J., and Castresana, C. (2005) Biochem. Biophys. Res. Commun. 338, 169-174
8. Hörnsten, L., Su, C., Osbourn, A. E., Garosi, P., Hellman, U., Wernstedt, C., and Oliw, E. H. (1999) J. Biol. Chem. 274, 28219-28224
9. Tsitsigiannis, D. I., Bok, J. W., Andes, D., Nielsen, K. F., Frisvad, J. C., and Keller, N. P. (2005) Infect. Immun. 73, 4548-4559
10. Malkowski, M. G., Ginell, S. L., Smith, W. L., and Garavito, R. M. (2000) Science 289, 1933-1937
11. Malkowski, M. G., Thuresson, E. D., Lakkides, K. M., Rieke, C. J., Micielli, R., Smith, W. L., and Garavito, R. M. (2001) J. Biol. Chem. 276, 37547-37555
12. Kiefer, J. R., Pawlitz, J. L., Moreland, K. T., Stegeman, R. A., Hood, W. F., Gierse, J. K., Stevens, A. M., Goodwin, D. C., Rowlinson, S. W., Marnett, L. J., Stallings, W. C., and Kurumbail, R. G. (2000) Nature 405, 97-101
13. Marnett, L. J., Rowlinson, S. W., Goodwin, D. C., Kalgutkar, A. S., and Lanzo, C. A. (1999) J. Biol. Chem. 274, 22903-22906
14. Kurumbail, R. G., Stevens, A. M., Gierse, J. K., McDonald, J. J., Stegeman, R. A., Pak, J. Y., Gildehaus, D., Miyashiro, J. M., Penning, T. D., Seibert, K., Isakson, P. C., and Stallings, W. C. (1996) Nature 384, 644-648
15. Smith, W. L., DeWitt, D. L., and Garavito, R. M. (2000) Annu. Rev. Biochem. 69, 145-182
16. Tsai, A., Hsi, L. C., Kulmacz, R. J., Palmer, G., and Smith, W. L. (1994) J. Biol. Chem. 269, 5085-5091
17. Koeduka, T., Matsui, K., Akakabe, Y., and Kajiwara, T. (2002) J. Biol. Chem. 277, 22648-22655
18. Garscha, U., and Oliw, E. H. (2008) FEBS Lett. 582, 3547-3551
19. Koszelak-Rosenblum, M., Krol, A. C., Simmons, D. M., Goulah, C. C., Wroblewski, L., and Malkowski, M. G. (2008) J. Biol. Chem. 283, 24962-24971
20. Garavito, R. M., Malkowski, M. G., and DeWitt, D. L. (2002) Prostaglandins Other Lipid Mediat. 68-69, 129-152
21. Cristea, M., Osbourn, A. E., and Oliw, E. H. (2003) Lipids 38, 1275-1280
22. Schneider, C., Boeglin, W. E., Prusakiewicz, J. J., Rowlinson, S. W., Marnett, L. J., Samel, N., and Brash, A. R. (2002) J. Biol. Chem. 277, 478-485
23. Thuresson, E. D., Lakkides, K. M., and Smith, W. L. (2000) J. Biol. Chem. 275, 8501-8507
24. Valmsen, K., Boeglin, W. E., Jarving, I., Schneider, C., Varvas, K., Brash, A. R., and Samel, N. (2004) Eur. J. Biochem. 271, 3533-3538
25. Harman, C. A., Rieke, C. J., Garavito, R. M., and Smith, W. L. (2004) J. Biol. Chem. 279, 42929-42935
26. Garscha, U., and Oliw, E. (2008) Biochem. Biophys. Res. Commun. 373, 579-583
27. Liu, J., Seibold, S. A., Rieke, C. J., Song, I., Cukier, R. I., and Smith, W. L. (2007) J. Biol. Chem. 282, 18233-18244
28. Garscha, U., and Oliw, E. H. (2007) Anal. Biochem. 367, 238-246
29. Oliw, E. H. (1983) J. Chromatogr. 275, 245-259
30. Cristea, M., and Oliw, E. H. (2007) J. Lipid Res. 48, 890-903
31. Cristea, M., Engström, Å., Su, C., Hörnsten, L., and Oliw, E. H. (2005) Arch. Biochem. Biophys. 434, 201-211
32. Oliw, E. H., Garscha, U., Nilsson, T., and Cristea, M. (2006) Anal. Biochem. 354, 111-12
33. Brash, A. R., Boeglin, W. E., Capdevila, J. H., Yeola, S., and Blair, I. A. (1995) Arch. Biochem. Biophys. 321, 485-492
34. Tsitsigiannis, D. I., and Keller, N. P. (2007) Trends Microbiol. 15, 109-118
35. Noverr, M. C., Toews, G. B., and Huffnagle, G. B. (2002) Infect. Immun. 70, 400-402
36. Milne, G. L., Yin, H., and Morrow, J. D. (2008) J. Biol. Chem. 283, 15533-15537
37. Schneider, C., and Brash, A. R. (2000) J. Biol. Chem. 275, 4743-4746
38. Thuresson, E. D., Lakkides, K. M., Rieke, C. J., Sun, Y., Wingerd, B. A., Micielli, R., Mulichak, A. M., Malkowski, M. G., Garavito, R. M., and Smith, W. L. (2001) J. Biol. Chem. 276, 10347-10357
39. Tsitsigiannis, D. I., Kowieski, T. M., Zarnowski, R., and Keller, N. P. (2004) Eukaryot. Cell 3, 1398-1411
40. Akakabe, Y., Matsui, K., and Kajiwara, T. (2005) Biosci. Biotechnol. Biochem. 69, 1539-1544
41. Wurzenberger, M., and Grosch, W. (1984) Biochim. Biophys. Res. Commun. 794, 18-24
42. Nemcovic, M., Jakubikova, L., Viden, I., and Farkas, V. (2008) FEMS Microbiol. Lett. 284, 231-236
43. Jones, D. T. (1999) J. Mol. Biol. 292, 195-202
44. Bylund, J., Ericsson, J., and Oliw, E. H. (1998) Anal. Biochem. 265, 55-68
45. Murphy, R. C., Barkley, R. M., Zemski Berry, K., Hankin, J., Harrison, K., Johnson, C., Krank, J., McAnoy, A., Uhlson, C., and Zarini, S. (2005) Anal. Biochem. 346, 1-42