Comparative functional characterization of a novel benzoate hydroxylase cytochrome P450 of Fusarium oxysporum

Enzyme and Microbial Technology

Volumn 70, Issue , 2015, Pages 58-65

  Durairaj, Pradeepraj ^a   Jung, Eunok ^b   Park, Hyun Ho ^a   Kim, Byung Gee ^b   Yun, Hyungdon ^c  

^a Yeungnam University   (South Korea)

^b Seoul National University   (South Korea)

^c Konkuk University   (South Korea)

Author keywords

Benzoate hydroxylase; CDNA gene cloning; Cytochrome P450; Cytochrome P450 reductase; Heterologous expression; Saccharomyces cerevisiae

Indexed keywords

CLONE CELLS; EFFICIENCY; HYDROXYLATION; YEAST;

CYTOCHROME P450; CYTOCHROME P450 REDUCTASE; GENE CLONING; HETEROLOGOUS EXPRESSION; HYDROXYLASES;

BENZOIC ACID;

3 METHOXYBENZOIC ACID; BENZOIC ACID; CYP53A19 PROTEIN; CYTOCHROME P450 REDUCTASE; GENOMIC DNA; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; BENZOATE 1,2-DIOXYGENASE; CYTOCHROME P450; FUNGAL PROTEIN; OXYGENASE; RECOMBINANT PROTEIN;

ARTICLE; CATALYSIS; DEMETHYLATION; ENZYME ACTIVITY; ENZYME SPECIFICITY; FUSARIUM OXYSPORUM; HETEROLOGOUS EXPRESSION; HYDROXYLATION; MICROSOME; NONHUMAN; AMINO ACID SEQUENCE; BIOTECHNOLOGY; CANDIDA ALBICANS; ENZYMOLOGY; FUNGAL GENE; FUSARIUM; GENETICS; METABOLISM; MOLECULAR GENETICS; OXIDATION REDUCTION REACTION; PHYLOGENY; SACCHAROMYCES CEREVISIAE; SEQUENCE HOMOLOGY;

CANDIDA ALBICANS; FUSARIUM OXYSPORUM; SACCHAROMYCES CEREVISIAE;

AMINO ACID SEQUENCE; BIOTECHNOLOGY; CANDIDA ALBICANS; CYTOCHROME P-450 ENZYME SYSTEM; FUNGAL PROTEINS; FUSARIUM; GENES, FUNGAL; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; OXYGENASES; PHYLOGENY; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 84921314946     PISSN: 01410229     EISSN: 18790909     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2014.12.013     Document Type: Article

References (30)

1. Črešnar B., Petrič Š. Cytochrome P450 enzymes in the fungal kingdom. Biochim Biophys Acta (BBA) - Proteins Proteomics 2011, 1814(1):29-35.
2. Braun A., Geier M., Bühler B., Schmid A., Mauersberger S., Glieder A. Steroid biotransformations in biphasic systems with Yarrowia lipolytica expressing human liver cytochrome P450 genes. Microb Cell Fact 2012, 11:106.
3. Sono M., Roach M.P., Coulter E.D., Dawson J.H. Heme-containing oxygenases. Chem Rev 1996, 96(7):2841-2888.
4. Jennewein S., Park H., DeJong J.M., Long R.M., Bollon A.P., Croteau R.B. Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 oxygenases involved in Taxol biosynthesis. Biotechnol Bioeng 2005, 89(5):588-598.
5. Ma L.-J., Van Der Does H.C., Borkovich K.A., Coleman J.J., Daboussi M.-J., Di Pietro A., et al. Comparative genomics reveals mobile pathogenicity chromosomes in Fusarium. Nature 2010, 464(7287):367-373.
6. Lah L., Podobnik B., Novak M., Korošec B., Berne S., Vogelsang M., et al. The versatility of the fungal cytochrome P450 monooxygenase system is instrumental in xenobiotic detoxification. Mol Microbiol 2011, 81(5):1374-1389.
7. Podobnik B., Stojan J., Lah L., Krasevec N., Seliskar M., Rizner T.L., et al. CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds. J Med Chem 2008, 51(12):3480-3486.
8. Harwood C.S., Parales R.E. The β-ketoadipate pathway and the biology of self-identity. Ann Rev Microbiol 1996, 50(1):553-590.
9. Matsuzaki F., Wariishi H. Molecular characterization of cytochrome P450 catalyzing hydroxylation of benzoates from the white-rot fungus Phanerochaete chrysosporium. Biochem Biophys Res Commun 2005, 334(4):1184-1190.
10. Faber B.W., van Gorcom R.F., Duine J.A. Purification and characterization of benzoate-para-hydroxylase, a cytochrome P450 (CYP53A1), from Aspergillus niger. Arch Biochem Biophys 2001, 394(2):245-254.
11. Jawallapersand P., Mashele S.S., Kovačič L., Stojan J., Komel R., Pakala S.B., et al. Cytochrome P450 monooxygenase CYP53 family in fungi: comparative structural and evolutionary analysis and its role as a common alternative anti-fungal drug target. PLOS ONE 2014, 9(9):e107209.
12. Park J., Lee S., Choi J., Ahn K., Park B., Park J., et al. Fungal cytochrome P450 database. BMC Genomics 2008, 9(1):402.
13. Harju S., Fedosyuk H., Peterson K.R. Rapid isolation of yeast genomic DNA: Bust n' Grab. BMC Biotechnol 2004, 4(1):8.
14. Tan S.-L., Dossett M., Katze M. Cryopreserved yeast cells suitable for routine, small-scale transformations. Biotechniques 1998, 25(5):792.
15. Stansfield I., Kelly S.L. Purification and quantification of Saccharomyces cerevisiae cytochrome P450. Yeast protocols 1996, 355-366. Springer.
16. Yim S.-K., Yun C.-H., Ahn T., Jung H.-C., Pan J.-G. A continuous spectrophotometric assay for NADPH-cytochrome P450 reductase activity using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide. J Biochem Mol Biol 2005, 38(3):366-369.
17. Nelson D.R. The cytochrome p450 homepage. Hum Genomics 2009, 4(1):59.
18. Fraser J.A., Davis M.A., Hynes M.J. The genes gmdA, encoding an amidase, and bzuA, encoding a cytochrome P450, are required for benzamide utilization in Aspergillus nidulans. Fungal Genet Biol 2002, 35(2):135-146.
19. Fukuda H., Nakamura K., Sukita E., Ogawa T., Fujii T. Cytochrome P450rm from Rhodotorula minuta catalyzes 4-hydroxylation of benzoate. J Biochem 1996, 119(2):314-318.
20. Zöllner A., Buchheit D., Meyer M.R., Maurer H.H., Peters F.T., Bureik M. Production of human phase 1 and 2 metabolites by whole-cell biotransformation with recombinant microbes. Bioanalysis 2010, 2(7):1277-1290.
21. Murakami H., Yabusaki Y., Sakaki T., Shibata M., Ohkawa H. Expression of cloned yeast NADPH-cytochrome P450 reductase gene in Saccharomyces cerevisiae. J Biochem 1990, 108(5):859-865.
22. Renaud J., Peyronneau M., Urban P., Truan G., Cullin C., Pompon D., et al. Recombinant yeast in drug metabolism. Toxicology 1993, 82(1):39-52.
23. Nazir K.N.H., Ichinose H., Wariishi H. Molecular characterization and isolation of cytochrome P450 genes from the filamentous fungus Aspergillus oryzae. Arch Microbiol 2010, 192(5):395-408.
24. Park H.-G., Lim Y.-R., Eun C.-Y., Han S., Han J.-S., Cho K.S., et al. Candida albicans NADPH-P450 reductase: expression, purification, and characterization of recombinant protein. Biochem Biophys Res Commun 2010, 396(2):534-538.
25. Pompon D., Louerat B., Bronine A., Urban P. Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol 1996, 272(B):51-64.
26. Kraus P., Kutchan T.M. Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a CO phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc Natl Acad Sci 1995, 92(6):2071-2075.
27. Dietrich M., Grundmann L., Kurr K., Valinotto L., Saussele T., Schmid R.D., et al. Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. ChemBioChem 2005, 6(11):2014-2022.
28. Lah L., Kraševec N., Trontelj P., Komel R. High diversity and complex evolution of fungal cytochrome P450 reductase: cytochrome P450 systems. Fungal Genet Biol 2008, 45:446-458.
29. Park S.-H., Kang J.-Y., Kim D.-H., Ahn T., Yun C.-H. The flavin-containing reductase domain of cytochrome P450 BM3 acts as a surrogate for mammalian NADPH-P450 reductase. Biomol Ther 2012, 20(6):562.
30. Sevrioukova I.F., Poulos T.L. Structural biology of redox partner interactions in P450cam monooxygenase: a fresh look at an old system. Arch Biochem Biophys 2011, 507(1):66-74.