Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli

Applied and Environmental Microbiology

Volumn 73, Issue 12, 2007, Pages 3877-3886

  Leonard, Effendi ^a   Lim, Kok Hong ^a   Saw, Phan Nee ^a   Koffas, Mattheos A G ^a  

^a the State University of New York   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONUNDRUM; FLAVANONES; GENOTYPE; PHOTORHABDUS LUMINESCENS; RECOMBINANT METABOLITES;

AROMATIC COMPOUNDS; BIOSYNTHESIS; ENZYME KINETICS; ESCHERICHIA COLI; METABOLISM; MOLECULAR BIOLOGY;

METABOLITES;

ACETIC ACID; ACETYL COENZYME A CARBOXYLASE; BIOTIN LIGASE; ERIODICTYOL; FLAVANONE DERIVATIVE; FLAVONOID; LIGASE; MALONYL COENZYME A; NARINGENIN; PINOCEMBRINE; UNCLASSIFIED DRUG;

BACTERIUM; BIOENGINEERING; ENZYME; METABOLISM; PIGMENT; RECOMBINATION;

AMINO TERMINAL SEQUENCE; ARTICLE; BACTERIAL METABOLISM; CARBOXY TERMINAL SEQUENCE; ENZYME ACTIVITY; ESCHERICHIA COLI; GENOTYPE; MACROMOLECULE; METABOLIC ENGINEERING; NONHUMAN; PHOTORHABDUS LUMINESCENS; PROMOTER REGION; PROTEIN EXPRESSION; SYNTHESIS;

ACETYL-COA CARBOXYLASE; CARBON-NITROGEN LIGASES; DNA PRIMERS; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; FLAVONOIDS; GENE EXPRESSION REGULATION, BACTERIAL; GENOTYPE; MALONYL COENZYME A; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR STRUCTURE; PROTEIN ENGINEERING; REPRESSOR PROTEINS; TRANSCRIPTION FACTORS;

ESCHERICHIA COLI; PHOTORHABDUS LUMINESCENS;

EID: 34250849659     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.00200-07     Document Type: Article

References (45)

1. Alper, H., Y. S. Jin, J. F. Moxley, and G. Stephanopoulos. 2005. Identifying gene targets for the metabolic engineering of lycopene biosynthesis in Escherichia coli. Metab. Eng. 7:155-164.
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. Balunas, M. J., and A. D. Kinghorn. 2005. Drug discovery from medicinal plants. Life Sci. 78:431-441.
4. Barker, D. F., and A. M. Campbell. 1980. Use of bio-lac fusion strains to study regulation of biotin biosynthesis in Escherichia coli. J. Bacteriol. 143: 789-800.
5. Burke, M. D., E. M. Berger, and S. L. Schreiber. 2004. A synthesis strategy yielding skeletally diverse small molecules combinatorially. J. Am. Chem. Soc. 126:14095-14104.
6. Butler, M. S. 2004. The role of natural product chemistry in drug discovery. J. Nat. Prod. 67:2141-2153.
7. Campbell, A., A. Del Campillo-Campbell, and R. Chang. 1972. A mutant of Escherichia coli that requires high concentrations of biotin. Proc. Natl. Acad. Sci. USA 69:676-680.
8. Campeau, E., and R. A. Gravel. 2001. Expression in Escherichia coli of N-and C-terminally deleted human holocarboxylase synthetase. Influence of the N-terminus on biotinylation and identification of a minimum functional protein. J. Biol. Chem. 276:12310-12316.
9. Chang, M. C., and J. D. Keasling. 2006. Production of isoprenoid pharmaceuticals by engineered microbes. Nat. Chem. Biol. 2:674-681.
10. Chapman-Smith, A., T. W. Morris, J. C. Wallace, and J. E. Cronan, Jr. 1999. Molecular recognition in a post-translational modification of exceptional specificity. Mutants of the biotinylated domain of acetyl-CoA carboxylase defective in recognition by biotin protein ligase. J. Biol. Chem. 274:1449-1457.
11. Chemler, J. A., Y. Yan, and M. A. Koffas. 2006. Biosynthesis of isoprenoids, polyunsaturated fatty acids and flavonoids in Saccharomyces cerevisiae. Microb. Cell Fact. 5:20.
12. Chin, Y. W., M. J. Balunas, H. B. Chai, and A. D. Kinghorn. 2006. Drug discovery from natural sources. AAPS J. 8:E239-E253.
13. Cirino, P. C., J. W. Chin, and L. O. Ingram. 2006. Engineering Escherichia coli for xylitol production from glucose-xylose mixtures. Biotechnol. Bioeng. 95:1167-1176.
14. Clarke, D. J., J. Coulson, R. Baillie, and D. J. Campopiano. 2003. Biotinylation in the hyperthermophile Aquifex aeolicus. Eur. J. Biochem. 270:1277-1287.
15. Cronan, J. E., Jr. 1988. Expression of the biotin biosynthetic operon of Escherichia coli is regulated by the rate of protein biotination. J. Biol. Chem. 263:10332-10336.
16. Davis, M. S., and J. E. Cronan, Jr. 2001. Inhibition of Escherichia coli acetyl coenzyme A carboxylase by acyl-acyl carrier protein. J. Bacteriol. 183:1499-1503.
17. Davis, M. S., J. Solbiati, and J. E. Cronan, Jr. 2000. Overproduction of acetyl-CoA carboxylase activity increases the rate of fatty acid biosynthesis in Escherichia coli. J. Biol. Chem. 275:28593-28598.
18. Demain, A. L. 2006. From natural products discovery to commercialization: a success story. J. Ind. Microbiol. Biotechnol. 33:486-495.
19. Eisenburg, M. A., B. Mee, O. Prakash, and M. R. Eisenburg. 1975. Properties of α-dehydrobiotin-resistant mutants of Escherichia coli K-12. J. Bacteriol. 122:66-72.
20. el-Mansi, E. M., and W. H. Holms. 1989. Control of carbon flux to acetate excretion during growth of Escherichia coli in batch and continuous cultures. J. Gen. Microbiol. 135:2875-2883.
21. Kirkpatrick, C., L. M. Maurer, N. E. Oyelakin, Y. N. Yoncheva, R. Maurer, and J. L. Slonczewski. 2001. Acetate and formate stress: opposite responses in the proteome of Escherichia coli. J. Bacteriol. 183:6466-6477.
22. Lee, W., T. K. Wood, and W. Chen. 2006. Engineering TCE-degrading rhizobacteria for heavy metal accumulation and enhanced TCE degradation. Biotechnol. Bioeng. 95:399-403.
23. Leonard, E., J. Chemler, K. H. Lim, and M. A. Koffas. 2006. Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli. Appl. Microbiol. Biotechnol. 70:85-91.
24. Leonard, E., Z. L. Fowler, and M. A. G. Koffas. 2007. Metabolic engineering, p. 301-359. In M. Al-Rubeai and M. Fusseneger (ed.), Systems biology, vol. 5. Springer, London, United Kingdom.
25. Leonard, E., Y. Yan, and M. A. Koffas. 2006. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng. 8:172-181.
26. 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.
27. Li, S. J., and J. E. Cronan, Jr. 1992. The gene encoding the biotin carboxylase subunit of Escherichia coli acetyl-CoA carboxylase. J. Biol. Chem. 267:855-863.
28. Li, S. J., and J. E. Cronan, Jr. 1992. The genes encoding the two carboxyltransferase subunits of Escherichia coli acetyl-CoA carboxylase. J. Biol. Chem. 267:16841-16847.
29. Li, S. J., and J. E. Cronan, Jr. 1993. Growth rate regulation of Escherichia coli acetyl coenzyme A carboxylase, which catalyzes the first committed step of lipid biosynthesis. J. Bacteriol. 175:332-340.
30. Lombardino, J. G., and J. A. Lowe III. 2004. The role of the medicinal chemist in drug discovery - then and now. Nat. Rev. Drug Discov. 3:853-862.
31. Luli, G. W., and W. R. Strohl. 1990. Comparison of growth, acetate production, and acetate inhibition of Escherichia coli strains in batch and fed-batch fermentations. Appl. Environ. Microbiol. 56:1004-1011.
32. Miyahisa, I., M. Kaneko, N. Funa, H. Kawasaki, H. Kojima, Y. Ohnishi, and S. Horinouchi. 2005. Efficient production of (2S)-fiavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Appl. Microbiol. Biotechnol. 68:498-504.
33. Paterson, I., and E. A. Anderson. 2005. Chemistry. The renaissance of natural products as drug candidates. Science 310:451-453.
34. Pruss, B. M., and A. J. Wolfe. 1994. Regulation of acetyl phosphate synthesis and degradation, and the control of flagellar expression in Escherichia coli. Mol. Microbiol. 12:973-984.
35. Reche, P. A., M. J. Howard, R. W. Broadhurst, and R. N. Perham. 2000. Heteronuclear NMR studies of the specificity of the post-translational modification of biotinyl domains by biotinyl protein ligase. FEBS Lett. 479:93-98.
36. Roe, A. J., D. McLaggan, I. Davidson, C. O'Byrne, and I. R. Booth. 1998. Perturbation of anion balance during inhibition of growth of Escherichia coli by weak acids. J. Bacteriol. 180:767-772.
37. Rui, L., L. Cao, W. Chen, K. F. Reardon, and T. K. Wood. 2004. Active site engineering of the epoxide hydrolase from Agrobacterium radiobacter AD1 to enhance aerobic mineralization of cis-1,2-dichloroethylene in cells expressing an evolved toluene ortho-monooxygenase. J. Biol. Chem. 279: 46810-46817.
38. Russell, J. B., and F. Diez-Gonzalez. 1998. The effects of fermentation acids on bacterial growth. Adv. Microb. Physiol. 39:205-234.
39. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
40. Stephanopoulos, G., and A. J. Sinskey. 1993. Metabolic engineering - methodologies and future prospects. Trends Biotechnol. 11:392-396.
41. Takamura, Y., and G. Nomura. 1988. Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12. J. Gen. Microbiol. 134:2249-2253.
42. Voigt, C. A., C. Martinez, Z. G. Wang, S. L. Mayo, and F. H. Arnold. 2002. Protein building blocks preserved by recombination. Nat. Struct. Biol. 9:553-558.
43. Weaver, L. H., K. Kwon, D. Beckett, and B. W. Matthews. 2001. Competing proteimprotein interactions are proposed to control the biological switch of the E coli biotin repressor. Protein Sci. 10:2618-2622.
44. Winkel-Shirley, B. 2001. Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol. 126:485-493.
45. Yan, Y. J., A. Kohli, and M. A. G. Koffas. 2005. Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 71:5610-5613.