Estriol bound and ligand-free structures of sterol 14α-demethylase

Structure

Volumn 12, Issue 11, 2004, Pages 1937-1945

  Podust, Larissa M ^a   Yermalitskaya, Liudmila V ^a   Lepesheva, Galina I ^a   Podust, Vladimir N ^b   Dalmasso, Enrique A ^b   Waterman, Michael R ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b CIPHERGEN BIOSYSTEMS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; ESTRIOL; STEROL 14ALPHA DEMETHYLASE;

ARTICLE; CANDIDA ALBICANS; CONFORMATION; CONTROLLED STUDY; DYNAMICS; GENE MUTATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN STRUCTURE; YEAST;

AMINO ACID SEQUENCE; CYTOCHROME P-450 ENZYME SYSTEM; ESTRIOL; LIGANDS; MODELS, MOLECULAR; MOLECULAR PROBES; MOLECULAR SEQUENCE DATA; OXIDOREDUCTASES; PROTEIN CONFORMATION; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY;

CANDIDA; CANDIDA ALBICANS; EUKARYOTA;

EID: 7944237907     PISSN: 09692126     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.str.2004.08.009     Document Type: Article

References (36)

1. Aoyama Y., Noshiro M., Gotoh O., Imaoka S., Funae Y., Kurosawa N., Horiuchi T., Yoshida Y. Sterol 14-demethylase P450 (P45014DM*) is one of the most ancient and conserved P450 species. J. Biochem. (Tokyo). 119:1996;926-933
2. Aoyama Y., Horiuchi T., Gotoh O., Noshiro M., Yoshida Y. CYP51-like gene of Micobacterium tuberculosis actually encodes a P450 similar to eukaryotic CYP51. J. Biochem. (Tokyo). 124:1998;694-696
3. Bellamine A., Mangla A.T., Nes W.D., Waterman M.R. Characterization and catalytic properties of the sterol 14alpha-demethylase from Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. USA. 96:1999;8937-8942
4. Bird C.W., Lynch J.M., Pirt F.J., Reid W.W. Steroids and squalene in Methylococcus capsulatus grown on methane. Nature. 230:1971;473-474
5. Bode H.B., Zeggel B., Silakowski B., Wenzel S.C., Reichenbach H., Muller R. Steroid biosynthesis in prokaryotes. identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca Mol. Microbiol. 47:2003;471-481
6. Brennan P.J., Nikaido H. The envelope of Mycobacteria. Annu. Rev. Biochem. 64:1995;29-63
7. Brunger A.T., Adams P.D., Clore G.M., Delano W.L., Gros P., Grosse-Kunstleve R.W., Jiang J.-S., Kuszewski J., Nilges M., Pannu N.S. Crystallography and NMR system. a new software suite for macromolecular structure determination Acta Crystallogr. D Biol. Crystallogr. 54:1998;905-921
8. Gollapudy R., Ajmani S., Kulkarni S.A. Modeling and interactions of Aspergillus fumigatus lanosterol 14-[alpha] demethylase 'A' with azole antifungals*1. Bioorg. Med. Chem. 12:2004;2937-2950
9. Gottesman M.E., Hendrickson W.A. Protein folding and unfolding by Escherichia coli chaperones and chaperonins. Curr. Opin. Microbiol. 3:2000;197-202
10. Gupta A.K., Tomas E. New antifungal agents. Dermatol. Clin. 21:2003;565-576
11. Houry W.A., Frishman D., Eckerskorn C., Lottspeich F., Hartl F.U. Identification of in vivo substrates of the chaperonin GroEL. Nature. 402:1999;147-154
12. Jackson C.J., Lamb D.C., Marczylo T.H., Warrilow A.G.S., Manning N.J., Lowe D.J., Kelly D.E., Kelly S.L. A novel sterol 14alpha-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. J. Biol. Chem. 277:2002;46959-46965
13. Jones T.A., Zou J.Y., Cowan S.W., Kjeldgaard M. Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr. A. 47:1991;110-119
14. Kohl W., Gloe A., Reichenbach H. Steroids from the myxobacterium Nannocystis exedens. J. Gen. Microbiol. 129:1983;1629-1635
15. Koltin Y., Hitchcock C.A. The search for new triazole antifungal agents. Curr. Opin. Chem. Biol. 1:1997;176-182
16. Laskowski R.A., MacArthur M.W., Moss D.S., Thornton J.M. Procheck. a program to check the stereochemical quality of protein structures J. Appl. Crystallogr. 26:1993;283-291
17. Lepesheva G.I., Podust L.M., Bellamine A., Waterman M.R. Folding requirements are different between sterol 14alpha-demethylase (CYP51) from Mycobacterium tuberculosis and human or fungal orthologs. J. Biol. Chem. 276:2001;28413-28420
18. Lepesheva G.I., Nes W.D., Zhou W., Hill G.C., Waterman M.R. CYP51 from Trypanosoma brucei is obtusifoliol-specific. Biochemistry. 43:2004;10789-10799
19. Marichal P., Koymans L., Willemsens S., Bellens D., Verhasselt P., Luyten W., Borgers M., Ramaekers F.C.S., Odds F.C., Bossche H.V. Contribution of mutations in the cytochrome P450 14α-demethylase (Erg11p, Cyp51p) to azole resistance in Candida albicans. Microbiol. 145:1999;2701-2713
20. Morschhauser J. The genetic basis of fluconazole resistance development in Candida albicans. Biochim. Biophys. Acta. 1587:2002;240-248
21. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J. Biol. Chem. 239:1964;2379-2385
22. Otwinowski Z., Minor W. Processing of x-ray diffraction data collected in oscillation mode. Methods Enzymol. 276:1997;307-326
23. Ourisson G., Nakatani Y. The terpenoid theory of the origin of cellular life. the evolution of terpenoids to cholesterol Chem. Biol. 1:1994;11-23
24. Park S.Y., Yamane K., Adachi S., Shiro Y., Weiss K.E., Maves S.A., Sligar S.G. Thermophilic cytochrome P450 (CYP119) from Sulfolobus solfataricus. high resolution structure and functional properties J. Inorg. Biochem. 91:2002;491-501
25. Pearson A., Budin M., Brocks J.J. Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus. Proc. Natl. Acad. Sci. USA. 100:2003;15352-15357
26. Podust L.M., Poulos T.L., Waterman M.R. Crystal structure of cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Proc. Natl. Acad. Sci. USA. 98:2001;3068-3073. a
27. Podust L.M., Stojan J., Poulos T.L., Waterman M.R. Substrate recognition sites in 14alpha-sterol demethylase from comparative analysis of amino acid sequences and X-ray structure of Mycobacterium tuberculosis CYP51. J. Inorg. Biochem. 87:2001;227-235. b
28. Podust L.M., Kim Y., Arase M., Neely B.A., Beck B.J., Bach H., Sherman D.H., Lamb D.C., Kelly S.L., Waterman M.R. The 1.92-A structure of Streptomyces coelicolor A3(2) CYP154C1. A new monooxygenase that functionalizes macrolide ring systems. J. Biol. Chem. 278:2003;12214-12221
29. Schouten S., Bowman J.P., Rijpstra W.I., Sinninghe Damste J.S. Sterols in a psychrophilic methanotroph, Methylosphaera hansonii. FEMS Microbiol. Lett. 186:2000;193-195
30. Scott E.E., He Y.A., Wester M.R., White M.A., Chin C.C., Halpert J.R., Johnson E.F., Stout C.D. An open conformation of mammalian cytochrome P450 2B4 at 1.6-A resolution. Proc. Natl. Acad. Sci. USA. 100:2003;13196-13201
31. Scott E.E., White M.A., He Y.A., Johnson E.F., Stout C.D., Halpert J.R. Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl) imidazole at 1.9-A resolution. insight into the range of P450 conformations and the coordination of redox partner binding J. Biol. Chem. 279:2004;27294-27301
32. Sheehan D.J., Hitchcoch C.A., Sibley C.M. Current and emerging azole antifungal agents. Clin. Microbiol. Rev. 12:1999;40-79
33. Sheldrick G.M. Phase annealing in SHELX-90. direct methods for larger structures Acta Crystallogr. A46:1990;467-473
34. Xiao L., Madison V., Chau A.S., Loebenberg D., Palermo R.E., McNicholas P.M. Three-dimensional models of wild-type and mutated forms of cytochrome P450 14alpha-sterol demethylases from Aspergillus fumigatus and Candida albicans provide insights into posaconazole binding. Antimicrob. Agents Chemother. 48:2004;568-574
35. Yano J.K., Koo L.S., Schuller D.J., Li H., Ortiz de Montellano P.R., Poulos T.L. Crystal structure of a thermophilic cytochrome P450 from the archaeon Sulfolobus solfataricus. J. Biol. Chem. 275:2000;31086-31092
36. Zerbe K., Pylypenko O., Vitali F., Zhang W., Rouset S., Heck M., Vrijbloed J.W., Bischoff D., Bister B., Sussmuth R.D., et al. Crystal structure of OxyB, a cytochrome P450 implicated in an oxidative phenol coupling reaction during vancomycin biosynthesis. J. Biol. Chem. 277:2002;47476-47485