Modeling the interfacial interactions between CrtS and CrtR from xanthophyllomyces dendrorhous, a P450 system involved in astaxanthin production

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 35, 2012, Pages 8640-8647

  Alcaíno, Jennifer ^a   Fuentealba, Matías ^b   Cabrera, Ricardo ^b   Baeza, Marcelo ^a   Cifuentes, Víctor ^a  

^a Centro de Biotecnologia   (Chile)

^b UNIVERSITY OF CHILE   (Chile)

Author keywords

astaxanthin synthase; cytochrome P450 reductase; FMN binding domain; protein complex modeling; Xanthophyllomyces dendrorhous

Indexed keywords

CYTOCHROME P450 REDUCTASE; FMN-BINDING DOMAIN; PROTEIN COMPLEXES; SYNTHASES; XANTHOPHYLLOMYCES DENDRORHOUS;

MAMMALS; MOLECULAR DYNAMICS;

YEAST;

ASTAXANTHIN; BETA CAROTENE; CYTOCHROME P450; FLAVINE MONONUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; XANTHOPHYLL;

ARTICLE; BASIDIOMYCETES; BINDING SITE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; GENETICS; METABOLISM; PROTEIN SECONDARY STRUCTURE;

BASIDIOMYCOTA; BETA CAROTENE; BINDING SITES; CYTOCHROME P-450 ENZYME SYSTEM; FLAVIN MONONUCLEOTIDE; MODELS, MOLECULAR; NADPH-FERRIHEMOPROTEIN REDUCTASE; PROTEIN STRUCTURE, SECONDARY; XANTHOPHYLLS;

MAMMALIA; SACCHAROMYCES CEREVISIAE; XANTHOPHYLLOMYCES; XANTHOPHYLLOMYCES DENDRORHOUS;

EID: 84865842002     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302287f     Document Type: Article

References (30)

1. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids. Vol. 3: Biosynthesis and Metabolism; Birkhäuser: Basel, Switzerland, 1998.
2. Walker, L. A.; Wang, T.; Xin, H.; Dolde, D. Supplementation of laying-hen feed with palm tocos and algae astaxanthin for egg yolk nutrient enrichment J. Agric. Food Chem. 2012, 60, 1989-1999
3. Kim, Y. J.; Kim, Y. A.; Yokozawa, T. Protection against oxidative stress, inflammation, and apoptosis of high-glucose-exposed proximal tubular epithelial cells by astaxanthin J. Agric. Food Chem. 2009, 57, 8793-8797
4. Higuera-Ciapara, I.; Felix-Valenzuela, L.; Goycoolea, F. M. Astaxanthin: a review of its chemistry and applications Crit. Rev. Food Sci. Nutr. 2006, 46, 185-196
5. álvarez, V.; Rodríguez-Sáiz, M.; de la Fuente, J. L.; Gudiña, E. J.; Godio, R. P.; Martín, J. F.; Barredo, J. L. The crtS gene of Xanthophyllomyces dendrorhous encodes a novel cytochrome-P450 hydroxylase involved in the conversion of β-carotene into astaxanthin and other xanthophylls Fungal Genet. Biol. 2006, 43, 261-272
6. Ojima, K.; Breitenbach, J.; Visser, H.; Setoguchi, Y.; Tabata, K.; Hoshino, T.; van den Berg, J.; Sandmann, G. Cloning of the astaxanthin synthase gene from Xanthophyllomyces dendrorhous (Phaffia rhodozyma) and its assignment as a β-carotene 3-hydroxylase/4-ketolase Mol. Genet. Genomics 2006, 275, 148-158 (Pubitemid 43228131)
7. van den Brink, H.; van Gorcom, R. F. M.; van den Hondel, C. A.; Punt, P. J. Cytochrome P450 enzyme systems in fungi Fungal Genet. Biol. 1998, 23, 1-17 (Pubitemid 28403134)
8. Alcaíno, J.; Barahona, S.; Carmona, M.; Lozano, C.; Marcoleta, A.; Niklitschek, M.; Sepúlveda, D.; Baeza, M.; Cifuentes, V. Cloning of the cytochrome p450 reductase (crtR) gene and its involvement in the astaxanthin biosynthesis of Xanthophyllomyces dendrorhous BMC Microbiol. 2008, 8, 169
9. Ukibe, K.; Hashida, K.; Yoshida, N.; Takagi, H. Metabolic engineering of Saccharomyces cerevisiae for astaxanthin production and oxidative stress tolerance Appl. Environ. Microbiol. 2009, 75, 7205-7211
10. Sevrioukova, I. F.; Li, H.; Zhang, H.; Peterson, J. A.; Poulos, T. L. Structure of a cytochrome P450-redox partner electron-transfer complex Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1863
11. Hamdane, D.; Xia, C.; Im, S. C.; Zhang, H.; Kim, J. J.; Waskell, L. Structure and function of an NADPH-cytochrome P450 oxidoreductase in an open conformation capable of reducing cytochrome P450 J. Biol. Chem. 2009, 284, 11374-11384
12. Kimmich, N.; Das, A.; Sevrioukova, I.; Meharenna, Y.; Sligar, S. G.; Poulos, T. L. Electron transfer between cytochrome P450cin and its FMN-containing redox partner, cindoxin J. Biol. Chem. 2007, 282, 27006-27011 (Pubitemid 47501928)
13. Cojocaru, V.; Balali-Mood, K.; Sansom, M. S. P.; Wade, R. C. Structure and dynamics of the membrane-bound cytochrome P450 2C9 PLoS Comput. Biol. 2011, 7, e1002152
14. Larkin, M. A.; Blackshields, G.; Brown, N. P.; Chenna, R.; McGettigan, P. A.; McWilliam, H.; Valentin, F.; Wallace, I. M.; Wilm, A.; Lopez, R. Clustal W and Clustal X version 2.0. Bioinformatics 2007, 23, 2947-2948.
15. Sali, A.; Blundell, T. L. Comparative protein modelling by satisfaction of spatial restraints J. Mol. Biol. 1993, 234, 779-815 (Pubitemid 24007801)
16. Sippl, M. J. Recognition of errors in three-dimensional structures of proteins Proteins 1993, 17, 355-362 (Pubitemid 23358545)
17. Eisenberg, D.; Lüthy, R.; Bowie, J. U. VERIFY3D: Assessment of protein models with three-dimensional profiles Methods Enzymol. 1997, 277, 396-404
18. Jones, D. T. Protein secondary structure prediction based on position-specific scoring matrices 1 J. Mol. Biol. 1999, 292, 195-202 (Pubitemid 29435759)
19. Humphrey, W.; Dalke, A.; Schulten, K. VMD: visual molecular dynamics J. Mol. Graph. 1996, 14, 33-38 (Pubitemid 26152973)
20. Phillips, J. C.; Braun, R.; Wang, W.; Gumbart, J.; Tajkhorshid, E.; Villa, E.; Chipot, C.; Skeel, R. D.; Kale, L.; Schulten, K. Scalable molecular dynamics with NAMD J. Comput. Chem. 2005, 26, 1781-1802 (Pubitemid 43078511)
21. MacKerell, A. D.; Bashford, D.; Bellott, M.; Dunbrack, R. L.; Evanseck, J. D.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S.; Joseph-McCarthy, D.; Kuchnir, L.; Kuczera, K.; Lau, F. T. K.; Mattos, C.; Michnick, S.; Ngo, T.; Nguyen, D. T.; Prodhom, B.; Reiher, W. E.; Roux, B.; Schlenkrich, M.; Smith, J. C.; Stote, R.; Straub, J.; Watanabe, M.; Wiorkiewicz-Kuczera, J.; Yin, D.; Karplus, M. All-atom empirical potential for molecular modeling and dynamics studies of proteins J. Phys. Chem. B 1998, 102, 3586-3616 (Pubitemid 128576688)
22. Freddolino, P. L.; Dittrich, M.; Schulten, K. Dynamic switching mechanisms in LOV1 and LOV2 domains of plant phototropins Biophys. J. 2006, 91, 3630-3639 (Pubitemid 44788306)
23. Dolinsky, T. J.; Nielsen, J. E.; McCammon, J. A.; Baker, N. A. PDB2PQR: an automated pipeline for the setup of Poisson-Boltzmann electrostatics calculations Nucleic Acids Res. 2004, 32, W665-W667
24. Cole, C.; Barber, J. D.; Barton, G. J. The Jpred 3 secondary structure prediction server Nucleic Acids Res. 2008, 36, W197-W201
25. Altschul, S. F.; Gish, W.; Miller, W.; Myers, E. W.; Lipman, D. J. Basic local alignment search tool J. Mol. Biol. 1990, 215, 403-410
26. Lamb, D. C.; Kim, Y.; Yermalitskaya, L. V.; Yermalitsky, V. N.; Lepesheva, G. I.; Kelly, S. L.; Waterman, M. R.; Podust, L. M. A second FMN binding site in yeast NADPH-cytochrome P450 reductase suggests a mechanism of electron transfer by diflavin reductases Structure 2006, 14, 51-61 (Pubitemid 43350073)
27. Ellis, J.; Gutierrez, A.; Barsukov, I. L.; Huang, W. C.; Grossmann, J. G.; Roberts, G. C. K. Domain motion in cytochrome P450 Reductase J. Biol. Chem. 2009, 284, 36628
28. Laursen, T.; Jensen, K.; Møller, B. L. Conformational changes of the NADPH-dependent cytochrome P450 reductase in the course of electron transfer to cytochromes P450 Biochim. Biophys. Acta-Proteins Proteomics 2011, 1814, 132-138
29. Sirim, D.; Widmann, M.; Wagner, F.; Pleiss, J. Prediction and analysis of the modular structure of cytochrome P450 monooxygenases BMC Struct. Biol. 2010, 10, 34
30. Bridges, A.; Gruenke, L.; Chang, Y. T.; Vakser, I. A.; Loew, G.; Waskell, L. Identification of the binding site on cytochrome P450 2B4 for cytochrome b5 and cytochrome P450 reductase J. Biol. Chem. 1998, 273, 17036-17049 (Pubitemid 28311737)