Styrene biosynthesis from glucose by engineered E. coli

Metabolic Engineering

Volumn 13, Issue 5, 2011, Pages 544-554

  McKenna, Rebekah ^a   Nielsen, David R ^a  

^a Arizona State University   (United States)

Author keywords

Aromatic; Cinnamic acid; E. coli; L Phenylalanine; Phenylalanine ammonia lyase; Styrene

Indexed keywords

AROMATIC; CINNAMIC ACIDS; E. COLI; L-PHENYLALANINE; PHENYLALANINE AMMONIA-LYASE;

AMINO ACIDS; AMMONIA; AROMATIC POLYMERS; BIOCHEMISTRY; ESCHERICHIA COLI; GLUCOSE; YEAST;

STYRENE;

CINNAMATE DECARBOXYLASE; GLUCOSE; ISOENZYME; PHENYLALANINE; PHENYLALANINE AMMONIA LYASE; STYRENE; TYROSINE; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; BACILLUS SUBTILIS; BACTERIUM CULTURE; ENZYME ACTIVITY; ESCHERICHIA COLI; METABOLIC ENGINEERING; NONHUMAN; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE;

ALDOSE-KETOSE ISOMERASES; ARABIDOPSIS; CARBOXY-LYASES; ESCHERICHIA COLI; GENE EXPRESSION; GLUCOSE; ORGANISMS, GENETICALLY MODIFIED; PHENYLALANINE; SACCHAROMYCES CEREVISIAE; STYRENE;

ARABIDOPSIS THALIANA; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; SACCHAROMYCES CEREVISIAE;

EID: 84857281676     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2011.06.005     Document Type: Article

References (58)

1. Alper H., Moxley J., Nevoigt E., Fink G.R., Stephanopoulos G. Engineering yeast transcription machinery for improved ethanol tolerance and production. Science 2006, 314:1565-1568.
2. Alper H., Stephanopoulos G. Global transcription machinery engineering: a new approach for improving cellular phenotype. Metabolic Engineering 2007, 9:258-267.
3. Babushok V.I., Linstrom P.J., Reed J.J., Zenkevich I.G., Brown R.L., Mallard W.G., Stein S.E. Development of a database of gas chromatographic retention properties of organic compounds. Journal of Chromatography A. 2007, 1157:414-421.
4. Baez-Viveros J.L., Osuna J., Hernandez-Chavez G., Soberon X., Bolivar F., Gosset G. Metabolic engineering and protein directed evolution increase the yield of l-phenylalanine synthesized from glucose in Escherichia coli. Biotechnology and Bioengineering 2004, 87:516-524.
5. Bonomo J., Warnecke T., Hume P., Marizcurrena A., Gill R.T. A comparative study of metabolic engineering anti-metabolite tolerance in Escherichia coli. Metabolic Engineering. 2006, 8:227-239.
6. Boudet A.M. Evolution and current status of research in phenolic compounds. Phytochemistry 2007, 68:2722-2735.
7. Clark G. Phenethyl alcohol. Perfumer Flavor 1990, 15:37-44.
8. Clausen M., Lamb C.J., Megnet R., Doerner P.W. PAD1 encodes phenylacrylic acid decarboxylase which confers resistance to cinnamic acid in Saccharomyces cerevisiae. Gene 1994, 142:107-112.
9. Cochrane F.C., Davin L.B., Lewis N.G. The Arabidopsis phenylalanine ammonia lyase gene family: kinetic characterization of the four PAL isoforms. Phytochemistry 2004, 65:1557-1564.
10. Cui J.D., Jia S.R., Sun A.Y. Influence of amino acids, organic solvents and surfactants for phenylalanine ammonia lyase activity in recombinant Escherichia coli. Letters in Applied Microbiology 2008, 46:631-635.
11. DoE, Steam system opportunity assessment for the pulp and paper, chemical manufacturing, and petroleum refining industries. In: Energy, O. o. E. E. a. R. E. U. S. D. o. (Ed.), 2002.
12. Fernandez X., Lizzani-Cuvelier L., Loiseau A.M., Perichet C., Delbecque C., Arnaudo J.F. Chemical composition of the essential oils from Turkish and Honduras Styrax. Flavour and Fragrance Journal 2005, 20:70-73.
13. Fischer C.R., Klein-Marcuschamer D., Stephanopoulos G. Selection and optimization of microbial hosts for biofuels production. Metabolic Engineering 2008, 10:295-304.
14. Flores N., Xiao J., Berry A., Bolivar F., Valle F. Pathway engineering for the production of aromatic compounds in Escherichia coli. Nature Biotechnology 1996, 14:620-623.
15. Gilbert H.J., Clarke I.N., Gibson R.K., Stephenson J.R., Tully M. Molecular-cloning of the phenylalanine ammonia-lyase gene from rhodosporidium-toruloides in Escherichia-coli K-12. Journal of Bacteriology 1985, 161:314-320.
16. Gilbert H.J., Stephenson J.R., Tully M. Control of synthesis of functional messenger-rna coding for phenylalanine ammonia-lyase from rhodosporidium-toruloides. Journal of Bacteriology 1983, 153:1147-1154.
17. Gilbert H.J., Tully M. Synthesis and degradation of phenylalanine ammonia-lyase of rhodosporidium-toruloides. Journal of Bacteriology 1982, 150:498-505.
18. Gosset G., Yong-Xiao J., Berry A. A direct comparison of approaches for increasing carbon flow to aromatic biosynthesis in Escherichia coli. Journal of Industrial Microbiology 1996, 17:47-52.
19. Gyamerah M., Glover J. Production of ethanol by continuous fermentation and liquid-liquid extraction. Journal of Chemical Technology and Biotechnology 1996, 66:145-152.
20. Heipieper H.J., Weber F.J., Sikkema J., Keweloh H., de Bont J.A.M. Mechanisms of resistance of whole cells to toxic organic solvents. Trends in Biotechnology 1994, 12:409-415.
21. Jain A.N., Khan T.R., Daugulis A.J. Bioproduction of benzaldehyde in a solid-liquid two-phase partitioning bioreactor using Pichia pastoris. Biotechnology Letters 2010, 32:1649-1654.
22. Jiang H., Wood K.V., Morgan J.A. Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae. Applied and Environmental Microbiology 2005, 71:2962-2969.
23. Jones D.H. Phenylalanine ammonia-lyase: regulation of its induction, and its role in plant development. Phytochemistry 1984, 23:1349-1359.
24. Keasling J.D. Synthetic biology for synthetic chemistry. ACS Chemical Biology 2008, 3:64-76.
25. Khan T.R., Daugulis A.J. Application of solid-liquid TPPBs to the production of l-phenylacetylcarbinol from benzaldehyde using Candida utilis. Biotechnology and Bioengineering 2010, 107:633-641.
26. Larsson S., Nilvebrant N.O., Jonsson L.J. Effect of overexpression of Saccharomyces cerevisiae Pad1p on the resistance to phenylacrylic acids and lignocellulose hydrolysates under aerobic and oxygen-limited conditions. Applied Microbiology and Biotechnology 2001, 57:167-174.
27. Loser C., Schroder A., Deponte S., Bley T. Balancing the ethanol formation in continuous bioreactors with ethanol stripping. Engineering in Life Sciences 2005, 5:325-332.
28. Lütke-Eversloh T., Stephanopoulos G. Combinatorial pathway analysis for improved l-tyrosine production in Escherichia coli: identification of enzymatic bottlenecks by systematic gene overexpression. Metabolic Engineering 2008, 10:69-77.
29. Malinowski J.J. Two-phase partitioning bioreactors in fermentation technology. Biotechnology Advances 2001, 19:525-538.
30. Moffitt M.C., Louie G.V., Bowman M.E., Pence J., Noel J.P., Moore B.S. Discovery of two cyanobacterial phenylalanine ammonia lyases: kinetic and structural characterization. Biochemistry 2007, 46:1004-1012.
31. Moffitt M.C., Louie G.V., Bowman M.E., Pence J., Noel J.P., Moore B.S. Discovery of two cyanobacterial phenylalanine ammonia lyases:{medium shade} kinetic and structural characterization. Biochemistry 2007, 46:1004-1012.
32. Mukai N., Masaki K., Fujii T., Kawamukai M., Iefuji H. PAD1 and FDC1 are essential for the decarboxylation of phenylacrylic acids in Saccharomyces cerevisiae. Journal of Bioscience and Bioengineering 2010, 109:564-569.
33. Nicolaou S.A., Gaida S.M., Papoutsakis E.T. A comparative view of metabolite and substrate stress and tolerance in microbial bioprocessing: from biofuels and chemicals, to biocatalysis and bioremediation. Metabolic Engineering 2010, 12:307-331.
34. Nielsen D.R., Amarasiriwardena G.S., Prather K.L.J. Predicting the adsorption of second generation biofuels by polymeric resins with applications for in situ product recovery (ISPR). Bioresource Technology 2010, 101:2762-2769.
35. Nielsen D.R., Leonard E., Yoon S.H., Tseng H.C., Yuan C., Prather K.L. Engineering alternative butanol production platforms in heterologous bacteria. Metabolic Engineering 2009.
36. Nielsen D.R., Prather K.J. In situ product recovery of n-butanol using polymeric resins. Biotechnology and Bioengineering 2009, 102:811-821.
37. Pagot Y., Belin J.M., Husson F., Spinnler H.E. Metabolism of phenylalanine and biosynthesis of styrene in Penicillium camemberti. Journal of Dairy Research 2007, 74:180-185.
38. Qi W.W., Vannelli T., Breinig S., Ben-Bassat A., Gatenby A.A., Haynie S.L., Sariaslani F.S. Functional expression of prokaryotic and eukaryotic genes in Escherichia coli for conversion of glucose to p-hydroxystyrene. Metabolic Engineering 2007, 9:268-276.
39. Ramos J.L., Duque E., Gallegos M.-T., Godoy P., Ramos-González M.I., Rojas A., Terán W., Segura A. Mechanisms of solvent tolerance in gram-negative bacteria. Annual Review of Microbiology 2002, 56:743-768.
40. Reyes L.H., Almario M.P., Kao K.C. Genomic library screens for genes involved in n-butanol tolerance in Escherichia coli. PLoS ONE 2011, 6:e17678.
41. Santos, C.N.S., Koffas, M., Stephanopoulos, G., 2011. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metabolic Engineering 13, 392-400.
42. SRI Styrene 2010, Access Intelligence LLC Inc.
43. Tatarko M., Romeo T. Disruption of a global regulatory gene to enhance central carbon flux into phenylalanine biosynthesis in Escherichia coli. Current Microbiology 2001, 43:26-32.
44. Tran N.P., Gury J., Dartois V., Nguyen T.K.C., Seraut H., Barthelmebs L., Gervais P., Cavin J.-F. Phenolic acid-mediated regulation of the padC gene, encoding the phenolic acid decarboxylase of Bacillus subtilis. Journal of Bacteriology 2008, 190:3213-3224.
45. Vane L.M. A review of pervaporation for product recovery from biomass fermentation processes. Journal of Chemical Technology and Biotechnology 2005, 80:603-629.
46. Vannelli T., Wei Qi, W., Sweigard J., Gatenby A.A., Sariaslani F.S. Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metabolic Engineering 2007, 9:142-151.
47. Vannelli T., Xue Z.X., Breinig S., Qi W.W., Sariaslani F.S. Functional expression in Escherichia coli of the tyrosine-inducible tyrosine ammonia-lyase enzyme from yeast Trichosporon cutaneum for production of p-hydroxycinnamic acid. Enzyme and Microbial Technology 2007, 41:413-422.
48. Verhoef S., Ruijssenaars H.J., de Bont J.A., Wery J. Bioproduction of p-hydroxybenzoate from renewable feedstock by solvent-tolerant Pseudomonas putida S12. Journal of Biotechnology 2007, 132:49-56.
49. Verhoef S., Wierckx N., Westerhof R.G., de Winde J.H., Ruijssenaars H.J. Bioproduction of p-hydroxystyrene from glucose by the solvent-tolerant bacterium Pseudomonas putida S12 in a two-phase water-decanol fermentation. Applied and Environmental Microbiology 2009, 75:931-936.
50. Weber F.J., Ooijkaas L.P., Schemen R.M., Hartmans S., de Bont J.A. Adaptation of Pseudomonas putida S12 to high concentrations of styrene and other organic solvents. Applied and Environmental Microbiology 1993, 59:3502-3504.
51. Weilnhammer C., Blass E. Continuous fermentation with product recovery by in-situ extraction. Chemical Engineering & Technology 1994, 17:365-373.
52. Wierckx N.J., Ballerstedt H., de Bont J.A., Wery J. Engineering of solvent-tolerant Pseudomonas putida S12 for bioproduction of phenol from glucose. Applied and Environmental Microbiology 2005, 71:8221-8227.
53. Wu, C., Koylinski, T., Bozik, J., 1981. Preparation of styrene from ethylbenzene US Patent 4,255,599.
54. Xiang L.K., Moore B.S. Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene. Journal of Biological Chemistry 2002, 277:32505-32509.
55. Xiang L.K., Moore B.S. Biochemical characterization of a prokaryotic phenylalanine ammonia lyase. Journal of Bacteriology 2005, 187:4286-4289.
56. Xiang L.K., Moore B.S. Biochemical characterization of a prokaryotic phenylalanine ammonia lyase (187, pg4286, 2005). Journal of Bacteriology 2006, 188:5331.
57. Yang C.L.Y.a.H.C. Henry's Law Constant for Compound in Water 1992, Gulf Publishing Company, Houston.
58. Young M.R., Towers G.H.N., Neish A.C. Taxonomic distribution of ammonia-lyases for l-phenylalanine and l-tyrosine in relation to lignification. Canadian Journal of Botany 1966, 44:341.