Phenylalanine 353 is a primary determinant for the positional specificity of mammalian 15-lipoxygenases

Journal of Molecular Biology

Volumn 264, Issue 5, 1996, Pages 1145-1153

  Borngräber, Sabine ^a   Kuban, Ralf Jürgen ^a   Anton, Monika ^a   Kühn, Hartmut ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

Atherosclerosis; Eicosanoids; Enzyme substrate interaction; Lipid peroxidation; Protein modeling

Indexed keywords

ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONIC ACID; CHIMERIC PROTEIN; PHENYLALANINE;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; RABBIT; RETICULOCYTE; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION;

EID: 0030596087     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1006/jmbi.1996.0702     Document Type: Article

References (31)

1. 2 torsional terms. J. Am. Chem. Soc. 99, 8127-8133.
2. Aqel, N. M., Ball, R. Y., Waldman, H. & Mitchinson, M. J. (1984). Monocytic origin of foam cells in human atherosclerotic plaques. Atherosclerosis, 53, 265-271.
3. Belkner, J., Wiesner, R., Rathmann, J., Barnett, J., Sigal, E. & Kühn, H. (1993). Oxygenation of lipoproteins by mammalian lipoxygenases. Eur J. Biochem. 213, 251-261.
4. Boyington, J. C., Gaffney, B. J. & Amzel, L. M. (1993). The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science, 260, 1482-1486.
5. Chen, X. S. & Funk, C. D. (1993). Structure-function properties of human platelet 12-lipoxygenase: chimeric enzyme and in vitro mutagenesis studies. FASEB J. 7, 694-701.
6. Chen, X. S., Kurre, U., Jenkins, N. A., Copeland, N. G. & Funk, C. D. (1994). cDNA cloning, expression, mutagenesis of C-terminal isoleucine, genomic structure, and chromosomal localizations of murine 12-lipoxygenases. J. Biol. Chem. 269, 13979-13987.
7. DeMarzo, N., Sloane, D. L., Dicharry, S., Highland, E. & Sigal, E. (1992). Cloning and expression of an airway epithelial 12-lipoxygenase. Am. J. Physiol. 262, L198-L207.
8. Fleming, J., Thiele, B. J., Chester, J., O'Prey, J., Janetzki, S., Aitken, A., Anton, I. A., Rapoport, S. M. & Harrison, P. R. (1989). The complete sequence of the rabbit erythroid cell-specific 15-lipoxygenase mRNA: comparison of the predicted amino acid sequence of the erythrocyte lipoxygenase with other lipoxygenases. Gene, 79, 181-188.
9. Folcik, V. A., Nivararisty, R. A., Krajewski, L. P. & Cathcart, M. K. (1995). Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques. J. Clin. Invest. 96, 504-510.
10. Freire-Moar, J., Alavi-Nassab, A., Ng, M., Mulkins, M. & Sigal, E. (1995). Cloning and characterization of a murine macrophage lipoxygenase. Biochim. Biophys. Acta, 1254, 112-116.
11. Funk, C. D., Furci, L. & FitzGerald, G. A. (1990). Molecular cloning, primary structure, and expression of the human platelet/erythroleukemia cell 12-lipoxygenase. Proc. Natl Acad. Sci. USA, 87, 5638-5642.
12. Hada, T., Hagiya, H., Suzuki, H., Arakawa, T., Nakamura, M., Matsuda, S., Yoshimoto, T., Yamamoto, S., Azekawa, T., Morita, Y., Ishimura, K. & Kim, H. Y. (1994). Arachidonate 12-lipoxygenase of rat pineal glands: catalytic properties and primary structure deduced from its cDNA. Biochim. Biophys. Acta, 1211, 221-228.
13. Hamberg, M. & Samuelsson, B. (1967). On the specificity of the oxygenation of unsaturated fatty acids catalyzed by soybean lipoxidase. J. Biol. Chem. 242, 5329-5335.
14. Horton, R. M. & Pease, L. R. (1991). Recombination and mutagenesis of DNA sequences using PCR. In Directed Mutagenesis (McPherson, M. J., ed.), pp. 217-247, Oxford University Press, New York.
15. Kühn, H., Schewe, T. & Rapoport, S. M. (1986). The stereochemistry of the reaction of lipoxygenases and their metabolites. A proposed nomenclature for lipoxygenases and related enzymes. Advan. Enzymol. 58, 273-311.
16. Kühn, H., Sprecher, H. & Brash, A. R. (1990). On the singular or dual positional specificity of lipoxygenases. J. Biol. Chem. 265, 16300-16305.
17. Kühn, H., Thiele, B. J., Ostareck-Lederer, A., Stender, H., Suzuki, H., Yoshimoto, T. & Yamamoto, S. (1993). Bacterial expression, purification and partial characterization of recombinant rabbit reticulocyte 15-lipoxygenase. Biochim. Biophys. Acta, 1168, 73-78.
18. Kühn, H., Belkner, J., Zaiss, S., Fährenklemper, T. & Wohlfeil, S. (1994). Involvement of 15-lipoxygenase in early stages of atherogenesis. J. Exp. Med. 179, 1903-1911.
19. Lehmann, W. D. (1994). Regio- and stereochemistry of the dioxygenation reaction catalyzed by (S)-type lipoxygenases or by the cyclooxygenase activity of prostaglandin H synthases. Free Radic. Biol. Med. 16, 241-253.
20. Prigge, S. T., Boyington, J. C., Gaffney, B. J. & Amzel, L. M. (1996). Structure conservation in lipoxygenases: structural analysis of soybean lipoxygenase-1 and modeling of human lipoxygenases. Proteins: Struct. Funct. Genet. 24, 275-291.
21. Samuelsson, B. E., Dahlén, S. E., Lindgren, J. A., Rouzer, C. A. & Serhan, C. N. (1987). Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science, 237, 1171-1176.
22. Schewe, T., Rapoport, S. M. & Kühn, H. (1986). Enzymology and physiology of reticulocyte lipoxygenase. Comparison with other lipoxygenases. Advan. Enzymol. 58, 191-271.
23. Sigal, E., Craik, C. S., Highland, E., Grunberger, D., Costello, L. L., Dixon, R. A. F. & Nadel, J. A. (1988). Molecular cloning and primary structure of human 15-lipoxygenase. Biochem. Biophys. Res. Commun. 157, 457-464.
24. Sloane, D. L., Leung, R., Craik, C. S. & Sigal, E. (1991). A primary determinant for lipoxygenase positional specificity. Nature, 354, 149-152.
25. Sloane, D. L., Leung, R., Barnett, J., Craik, C. S. & Sigal, E. (1995). Conversion of human 15-lipoxygenase to an efficient 12-lipoxygenase: the side-chain geometry of amino acids 417 and 418 determines positional specificity. Protein Eng. 8, 275-282.
26. Suzuki, H., Kishimoto, K., Yoshimoto, T., Yamamoto, S., Kanai, F., Ebina, Y., Miyatake, A. & Tanabe, T. (1994). Site-directed mutagenesis studies on the iron-binding domain and the determinant for the substrate oxygenation site of porcine leukocyte arachidonate 12-lipoxygenase. Biochim. Biophys. Acta, 1210, 308-316.
27. Watanabe, T. & Haeggström, J. Z. (1993). Rat 12-lipoxygenase: mutations of amino acids implicated in the positional specificity of 15- and 12-lipoxygenases. Biochem. Biophys. Res. Commun. 192, 1023-1029.
28. Watanabe, T., Medina, J. F., Haeggström, J. Z., Radmark, O. & Samuelsson, B. (1993). Molecular cloning of a 12-lipoxygenase cDNA from rat brain. Eur. J. Biochem. 212, 605-612.
29. Yamamoto, S. (1992). Mammalian lipoxygenases: molecular structures and functions. Biochim. Biophys. Acta, 1128, 117-131.
30. Ylä-Herttuala, S., Rosenfeld, M. E., Parthasarathy, S., Glass, C. S., Sigal, E., Witztum, J. L. & Steinberg, D. (1991). Gene expression in macrophage-rich human atherosclerotic lesions. J. Clin. Invest. 87, 1146-1152.
31. Yoshimoto, T., Suzuki, H., Yamamoto, S., Takai, T., Yokoyama, C. & Tanabe, T. (1990). Cloning and sequence analysis of the cDNA for arachidonate 12-lipoxygenase of porcine leukocytes. Proc. Natl Acad. Sci. USA, 87, 2142-2146.