Engineering of artificial plant cytochrome P450 enzymes for synthesis of isoflavones by Escherichia coli

Applied and Environmental Microbiology

Volumn 73, Issue 22, 2007, Pages 7246-7251

  Leonard, Effendi ^a   Koffas, Mattheos A G ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTIFICIAL ISOFLAVONE SYNTHASIS; CHIMERA; EUKARYOTIC HOSTS; PLANT ESTROGEN;

ESCHERICHIA COLI; HORMONES; PLANTS (BOTANY); PROTEINS;

ENZYME ACTIVITY;

CYTOCHROME P450; ESTROGEN; ISOFLAVONE DERIVATIVE; ISOFLAVONE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

COLIFORM BACTERIUM; ENZYME; ESTROGENIC COMPOUND; GENE EXPRESSION; GENETIC ENGINEERING; LABORATORY METHOD; ORGANIC COMPOUND; PROKARYOTE;

ARTICLE; BACTERIAL MEMBRANE; BACTERIAL STRAIN; CATALYSIS; CHIMERA; DEVICE; ENZYME ACTIVITY; ENZYME ENGINEERING; ESCHERICHIA COLI; GENETIC ENGINEERING; MOLECULAR RECOGNITION; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTEIN ASSEMBLY; PROTEIN EXPRESSION;

AMINO ACID SEQUENCE; BASE SEQUENCE; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; GENETIC ENGINEERING; ISOFLAVONES; MODELS, GENETIC; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OXYGENASES; PLANT PROTEINS; RECOMBINANT FUSION PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; SEQUENCE HOMOLOGY, NUCLEIC ACID;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; EUKARYOTA; PROKARYOTA;

EID: 36649037393     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.01411-07     Document Type: Article

References (32)

1. Akashi, T., T. Aoki, and S. Ayabe. 1999. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol. 121: 821-828.
2. Alper, H., K. Miyaoku, and G. Stephanopoulos. 2005. Construction of lycopene-overproducing E. coli strains by combining systematic and combinatorial gene knockout targets. Nat. Biotechnol. 23:612-616.
3. Altaras, N. E., and D. C. Cameron. 1999. Metabolic engineering of a 1,2-propanediol pathway in Escherichia coli. Appl. Environ. Microbiol. 65:1180-1185.
4. Barnes, H. J., M. P. Arlotto, and M. R. Waterman. 1991. Expression and enzymatic activity of recombinant cytochrome P450 17 alpha-hydroxylase in Escherichia coli. Proc. Natl. Acad. Sci. USA 88:5597-5601.
5. Burbulis, I. E., and B. Winkel-Shirley. 1999. Interactions among enzymes of the Arabidopsis flavonoid biosynthetic pathway. Proc. Natl. Acad. Sci. USA 96:12929-12934.
6. Carter, O. A., R. J. Peters, and R. Croteau. 2003. Monoterpene biosynthesis pathway construction in Escherichia coli. Phytochemistry 64:425-433.
7. Causey, T. B., S. Zhou, K. T. Shanmugam, and L. O. Ingram. 2003. Engineering the metabolism of Escherichia coli W3110 for the conversion of sugar to redox-neutral and oxidized products: homoacetate production. Proc. Natl. Acad. Sci. USA 100:825-832.
8. Chang, M. C., and J. D. Keasling. 2006. Production of isoprenoid pharmaceuticals by engineered microbes. Nat. Chem. Biol. 2:674-681.
9. Chemler, J. A., Y. Yan, E. Leonard, and M. A. Koffas. 2007. Combinatorial mutasynthesis of flavonoid analogues from acrylic acids in microorganisms. Org. Lett. 9:1855-1858.
10. Draths, K. M., D. R. Knop, and J. W. Frost. 1999. Shikimic acid and quinic acid: replacing isolation from plant sources with recombinant microbial biocatalysis. J. Am. Chem. Soc. 121:1603-1604.
11. Halkier, B. A., H. L. Nielsen, B. Koch, and B. L. Moller. 1995. Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli. Arch. Biochem. Biophys. 322:369-377.
12. Hotze, M., G. Schroder, and J. Schroder. 1995. Cinnamate 4-hydroxylase from Catharanthus roseus, and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli. FEBS Lett. 374:345-350.
13. Huang, Q., C. A. Roessner, R. Croteau, and A. I. Scott. 2001. Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorg. Med. Chem. 9:2237-2242.
14. Joo, H., Z. Lin, and F. H. Arnold. 1999. Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature 399:670-673.
15. Jung, W., O. Yu, S. M. Lau, D. P. O'Keefe, J. Odell, G. Fader, and B. McGonigle. 2000. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat. Biotechnol. 18:208-212.
16. Koepp, A. E., M. Hezari, J. Zajicek, B. S. Vogel, R. E. LaFever, N. G. Lewis, and R. Croteau. 1995. Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in Pacific yew. J. Biol. Chem. 270:8686-8690.
17. Leonard, E., K. H. Lim, P. N. Saw, and M. A. Koffas. 2007. Engineering central metabolic pathways for high-level fiavonoid production in Escherichia coli. Appl. Environ. Microbiol. 73:3877-3886.
18. Leonard, E., Y. Yan, and M. A. Koffas. 2006. Functional expression of a P450 fiavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng. 8:172-181.
19. Leonard, E., Y. Yan, K. H. Lim, and M. A. Koffas. 2005. Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 71:8241-8248.
20. Liu, C. J., J. W. Blount, C. L. Steele, and R. A. Dixon. 2002. Bottlenecks for metabolic engineering of isoflavone glycoconjugates in Arabidopsis. Proc. Natl. Acad. Sci. USA 99:14578-14583.
21. Martin, V. J. J., D. J. Pitera, S. T. Withers, J. D. Newman, and J. D. Keasling. 2003. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat. Biotechnol. 21:796-802.
22. Miura, Y., and A. J. Fulco. 1974. (ω-2) hydroxylation of fatty acids by a soluble system from Bacillus megaterium. J. Biol. Chem. 249:1880-1888.
23. Nielsen, J. S., and B. L. Moller. 2000. Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima. Plant Physiol. 122:1311-1321.
24. Otey, C. R., M. Landwehr, J. B. Endelman, K. Hiraga, J. D. Bloom, and F. H. Arnold. 2006. Structure-guided recombination creates an artificial family of cytochromes P450. PLoS Biol. 4:e112.
25. Paterson, I., and E. A. Anderson. 2005. Chemistry. The renaissance of natural products as drug candidates. Science 310:451-453.
26. Pfeifer, B. A., S. J. Admiraal, H. Gramajo, D. E. Cane, and C. Khosla. 2001. Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli. Science 291:1790-1792.
27. Sevrioukova, I. F., H. Li, H. Zhang, J. A. Peterson, and T. L. Poulos. 1999. Structure of a cytochrome P450-redox partner electron-transfer complex. Proc. Natl. Acad. Sci. USA 96:1863-1868.
28. Steele, C. L., M. Gyzen, D. Qutob, and R. A. Dixon. 1999. Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean. Arch. Biochem. Biophys. 367:146-150.
29. Williams, P. A., J. Cosme, V. Sridhar, E. F. Johnson, and D. E. McRee. 2000. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol. Cell 5:121-131.
30. Williams, P. A., J. Cosme, V. Sridhar, E. F. Johnson, and D. E. McRee. 2000. Microsomal cytochrome P450 2C5: comparison to microbial P450s and unique features. J. Inorg. Biochem. 81:183-190.
31. Yamazaki, S., K. Sato, K. Suhara, M. Sakaguchi, K. Mihara, and T. Omura. 1993. Importance of the proline-rich region following signal-anchor sequence in the formation of correct conformation of microsomal cytochrome P-450s. J. Biochem. (Tokyo) 114:652-657.
32. Yu, O., J. Shi, A. O. Hession, C. A. Maxwell, B. McGonigle, and J. T. Odell. 2003. Metabolic engineering to increase isoflavone biosynthesis in soybean seed. Phytochemistty 63:753-763.