Engineering Escherichia coli for production of functionalized terpenoids using plant P450s

Nature Chemical Biology

Volumn 3, Issue 5, 2007, Pages 274-277

  Chang, Michelle C Y ^a   Eachus, Rachel A ^a   Trieu, William ^a   Ro, Dae Kyun ^a   Keasling, Jay D ^a,b,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b University of California   (United States)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYCADINENE; AMORPHADIENE; ARTEMISINIC ACID; ARTEMISININ; CYTOCHROME P450; DRUG METABOLITE; GOSSYPOL; NATURAL PRODUCT; PACLITAXEL; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOENGINEERING; CONTROLLED STUDY; DRUG INDUSTRY; DRUG ISOLATION; DRUG MANUFACTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; HOST; IN VIVO STUDY; MASS SPECTROMETRY; NONHUMAN; PLANT; PRIORITY JOURNAL; PROTEIN SYNTHESIS; TITRIMETRY;

ESCHERICHIA COLI;

EID: 34247182988     PISSN: 15524450     EISSN: 15524469     Source Type: Journal    
DOI: 10.1038/nchembio875     Document Type: Article

References (29)

1. Conolly, J.D. & Hill, R.A. Dictionary of Terpenoids (Chapman & Hall, London, 1991).
2. Durst, F. & Nelson, D.R. Diversity and evolution of plant P450 and P450-reductases. Drug Metabol. Drug Interact. 12, 189-206 (1995).
3. Schuler, M.A. & Werck-Reichhart, D. Functional genomics of P450s. Annu. Rev. Plant Biol. 54, 629-667 (2003).
4. Chau, M., Jennewein, S., Walker, K. & Croteau, R. Taxol biosynthesis: molecular cloning and characterization of a cytochrome P450 taxoid 7β-hydroxylase. Chem. Biol. 11, 663-672 (2004).
5. Ortiz de Montellano, P. Cytochrome P450: Structure, Mechanism, and Biochemistry (Springer, New York, 2004).
6. Sono, M., Roach, M.P., Coulter, E.D. & Dawson, J.H. Heme-containing oxygenases. Chem. Rev. 96, 2841-2887 (1996).
7. Wuts, P.G.M. Semisynthesis of taxol. Curr. Opin. Drug Discov. Devel. 1, 329-337 (1998).
8. Roth, R.J. & Acton, N. A simple conversion of artemisinic acid into artemisinin. J. Nat. Prod. 52, 1183-1185 (1989).
9. Wittstock, U. & Halkier, B.A. Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L- phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate. J. Biol. Chem. 275, 14659-14666 (2000).
10. Hansen, C.H. et al. Cytochrome P450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. J. Biol. Chem. 276, 24790-24796 (2001).
11. Naur, P. et al. CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime. Arch. Biochem. Biophys. 409, 235-241 (2003).
12. Haudenschild, C., Schalk, M., Karp, F. & Croteau, R. Functional expression of regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha spp.) in Escherichia coli and Saccharomyces cerevisiae. Arch. Biochem. Biophys. 379, 127-136 (2000).
13. Bertea, C.M., Schalk, M., Karp, F., Maffei, M. & Croteau, R. Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. Arch. Biochem. Biophys. 390, 279-286 (2001).
14. Schroder, G. et al. Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase. FEBS Lett. 458, 97-102 (1999).
15. Irmler, S. et al. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 24, 797-804 (2000).
16. Leonard, E., Yan, Y. & Mattheos, M.A.G. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng. 8, 172-181 (2006).
17. Carter, O.A., Peters, R.J. & Croteau, R. Monoterpene biosynthesis pathway construction in Escherichia coli. Phytochemistry 64, 425-433 (2003).
18. Martin, V.J., Pitera, D.J., Withers, S.T., Newman, J.D. & Keasling, J.D. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat. Biotechnol. 21, 796-802 (2003).
19. Newman, J.D. et al. High-level production of amorpha-4,11-diene in a two-phase partitioning bioreactor of metabolically engineered Escherichia coli. Biotechnol. Bioeng. 95, 684-691 (2006).
20. Luo, P., Wang, Y.-H., Wang, G.-D., Essenberg, M. & Chen, X.-Y. Molecular cloning and functional identification of (+)-δ-cadinene-8- hydroxylase, a cytochrome P450 monooxygenase (CYP706B1) of cotton sesquiterpene biosynthesis. Plant J. 28, 95-104 (2001).
21. Ro, D.K. et al. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440, 940-943 (2006).
22. Sutter, T.R., Sanglard, D. & Loper, J.C. Isolation and characterization of the alkane-inducible NADPH-cytochrome P-450 oxidoreductase gene from Candida tropicalis. Identification of invariant residues within similar amino acid sequences of divergent flavoproteins. J. Biol. Chem. 265, 16428-16436 (1990).
23. Chen, X.Y., Chen, Y., Heinstein, P. & Davisson, V.J. Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis. Arch. Biochem. Biophys. 324, 255-266 (1995).
24. Craft, D.L., Madduri, K.M., Eshoo, M. & Wilson, C.R. Identification and characterization of the CYP52 family of Candida tropicalis ATCC 20336, important for the conversion of fatty acids and alkanes to α,ω-dicarboxylic acids. Appl. Environ. Microbiol. 69, 5983-5991 (2003).
25. Barnes, H.J., Arlotto, M.P. & Waterman, M.R. Expression and enzymatic activity of recombinant cytochrome P450 17-́-hydroxylase in Escherichia coli. Proc. Natl. Acad. Sci. USA 88, 5597-5601 (1991).
26. Schafmeister, C.E., Miercke, L.J.W. & Stroud, R.M. Structure at 2.5 A° of a designed peptide that maintains solubility of membrane proteins. Science 262, 734-738 (1993).
27. Sueyoshi, T., Park, L.J., Moore, R., Juvonen, R.O. & Negishi, M. Molecular engineering of microsomal P450 2́-4 to a stable, water-soluble enzyme. Arch. Biochem. Biophys. 322, 265-271 (1995).
28. Schoch, G.A., Attias, R., Belghazi, M., Dansette, P.M. & Werck-Reichhart, D. Engineering of a water-soluble plant cytochrome P450, CYP73A1, and NMR-based orientation of natural and alternate substrates in the active site. Plant Physiol. 133, 1198-1208 (2003).
29. Roosild, T.P. et al. NMR structure of Mistic, a membrane-integrating protein for membrane protein expression. Science 307, 1317-1321 (2005).