Perspectives of biotechnological production of L-tyrosine and its applications

Applied Microbiology and Biotechnology

Volumn 77, Issue 4, 2007, Pages 751-762

  Lütke Eversloh, Tina ^a,b   Santos, Christine Nicole S ^a   Stephanopoulos, Gregory ^a  

^a Massachusetts Institute of Technology   (United States)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Aromatic amino acids; Corynebacterium glutamicum; Escherichia coli; Metabolic engineering; Tyrosine; Tyrosine phenol lyase

Indexed keywords

AROMATIC COMPOUNDS; BIOCATALYSTS; BIOMASS; BIOTECHNOLOGY; ESCHERICHIA COLI; METABOLITES;

AROMATIC AMINO ACIDS; BIOMASS FEEDSTOCKS; CORYNEBACTERIUM GLUTAMICUM; METABOLIC ENGINEERING; TYROSINE; TYROSINE PHENOL LYASE;

AMINO ACIDS;

CARBIDOPA; LEVODOPA; PHENOL; PROTEIN HYDROLYSATE; SERINE; TYROSINE; TYROSINE PHENOL LYASE;

AMINO ACID; BACTERIUM; BIOENGINEERING; BIOTECHNOLOGY; METABOLISM;

AMINO ACID SYNTHESIS; ARTHROBACTER GLOBIFORMIS; BACTERIAL STRAIN; BIOCATALYST; BIOENGINEERING; BIOMASS; BIOTECHNOLOGICAL PROCEDURES; BIOTECHNOLOGICAL PRODUCTION; CATALYSIS; CHEMICAL REACTION; CITROBACTER FREUNDII; CORYNEBACTERIUM GLUTAMICUM; DIET SUPPLEMENTATION; DRUG MANUFACTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GENETIC MANIPULATION; HUMAN; KLEBSIELLA AEROGENES; NONHUMAN; PANTOEA AGGLOMERANS; PARKINSON DISEASE; PHENYLKETONURIA; PSEUDOMONAS AERUGINOSA; RECOMBINANT DNA TECHNOLOGY; RHODOCOCCUS ERYTHROPOLIS; SHORT SURVEY;

AMINO ACIDS; BACTERIA; BACTERIAL PHYSIOLOGY; BIOTECHNOLOGY; GENETIC ENGINEERING; TYROSINE; TYROSINE PHENOL-LYASE;

BACTERIA (MICROORGANISMS); CORYNEBACTERIUM GLUTAMICUM; ESCHERICHIA COLI;

EID: 36349029157     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-007-1243-y     Document Type: Short Survey

References (107)

1. Adelberg EA (1958) Selection of bacterial mutants which excrete antagonists of antimetabolites. J Bacteriol 76:326
2. Bailey JE (1991) Towards a science of metabolic engineering. Science 252:1668-1674
3. Bailey JE, Sburlati A, Hatzimanikatis V, Lee K, Renner WA, Tsai PS (1996) Inverse metabolic engineering: a strategy for directed genetic engineering of useful phenotypes. Biotechnol Bioeng 52:109-121
4. Barnett HM (1935) Method of preparing leucine. US Patent no. US 2,009,868
5. Bell AA, Wheeler MH (1986) Biosynthesis and functions of fungal melanins. Annu Rev Phytopathol 24:411-451
6. Berry A (1996) Improving production of aromatic compounds in Escherichia coli by metabolic engineering. Trends Biotechnol 14:250-256
7. Bongaerts J, Krämer M, Müller U, Raeven L, Wubbolts M (2001) Metabolic engineering for microbial production of aromatic amino acids and derived compounds. Metab Eng 3:289-300
8. Bonuccelli U, Del Dotto P (2006) New pharmacologic horizons in the treatment of Parkinson disease. Neurology 67:S30-S38
9. Breuer M, Ditrich K, Habicher T, Hauer B, Keßeler M, Stürmer R, Zelinski T (2004) Industrial methods for the production of optically active intermediates. Angew Chem Int Ed 43:788-824
10. Burkovski A, Krämer R (2002) Bacterial amino acid transport proteins: occurrence, functions, and significance for biotechnological applications. Appl Microbiol Biotechnol 58:265-274
11. Cabrera-Valladares N, Martínez A, Pinero S, Lagunas-Muñoz VH, Tinoco R, de Anda R, Vazquez-Duhalt R, Bolívar F, Gosset G (2006) Expression of the melA gene from Rhizobium etli CFN42 in Escherichia coli and characterization of the encoded tyrosinase. Enzyme Microb Technol 38:772-779
12. Cardinal EV (1953) Separation of tyrosine and cystine. US Patent no. US 2,650,242
13. Chandran SS, Yi J, Draths KM, von Daeniken R, Weber W, Frost JW (2003) Phosphoenolpyruvate availability and the biosynthesis of shikimic acid. Biotechnol Prog 19:808-814
14. Chen S, Vincent S, Wilson DB, Ganem B (2003) Mapping of chorismate mutase and prephenate dehydrogenase domains in the Escherichia coli T-protein. Eur J Biochem 270:757-763
15. Cohen GN, Adelberg EA (1958) Kinetics of incorporation of p-fluorophenylalanine by a mutant of Escherichia coli resistant to this analogue. J Bacteriol 76:328-330
16. Deijen JB, Orlebeke JF (1994) Effect of tyrosine on cognitive function and blood pressure under stress. Brain Res Bull 33:319-23
17. Dell KA, Frost JW (1993) Identification and removal of impediments to biocatalytic synthesis of aromatics from D-glucose: rate-limiting enzymes in the common pathway of aromatic amino acid biosynthesis. J Am Chem Soc 115:11581-11589
18. della-Cioppa G, Garger SJ, Sverlow GG, Turpen TH, Grill LK (1990) Melanin production in Escherichia coli from a cloned tyrosinase gene. Biotechnology 8:634-638
19. Dewick PM (1998) The biosynthesis of shikimate metabolites. Nat Prod Rep 15:17-58
20. Doroshenko V, Airich L, Vitushkina M, Kolokolova A, Livshits V, Mashko S (2007) YddG from Escherichia coli promotes export of aromatic amino acids. FEMS Microbiol Lett 275:312-318
21. Dosselaere F, Vanderleyden J (2001) A metabolic node in action: chorismate-utilizing enzymes in microorganisms. Crit Rev Microbiol 27:75-131
22. Enei H, Matsui H, Yamashita K, Okumura S, Yamada H (1972a) Distribution of tyrosine phenol lyase in microorganisms. Agric Biol Chem 36:1861-1868
23. Enei H, Nakazawa H, Matsui H, Okumura S, Yamada H (1972b) Enzymatic preparation of L-tyrosine or 3,4-dihydroxyphenyl-L-alanine from pyruvate, ammonia and phenol or pyrocatechol. FEBS Lett 21:39-41
24. Enei H, Matsui H, Nakazawa H, Okumura S (1973a) Synthesis of L-tyrosine or 3,4-dihydroxyphenyl-L-alanine from DL-serine and phenol or pyrocathechol. Agric Biol Chem 37:493-499
25. Enei H, Nakazawa H, Okumura S, Yamada H (1973b) Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. 5. Synthesis of L-tyrosine or 3,4-dihydroxyphenyl-L-alanine from pyruvic acid, ammonia and phenol or pyrocatechol. Agric Biol Chem 37:725-735
26. Fazel AM, Jensen RA (1979) Obligatory biosynthesis of L-tyrosine via pretyrosine branchlet in coryneform bacteria. J Bacteriol 138:805-815
27. Fazel AM, Jensen RA (1980) Arogenate (pretyrosine) is an obligatory intermediate of L-tyrosine biosynthesis: confirmation in a microbial mutant. Proc Natl Acad Sci USA 77:1270-1273
28. Flores N, Xiao J, Berry A, Bolivar F, Valle F (1996) Pathway engineering for the production of aromatic compounds in Escherichia coli. Nat Biotechnol 14:620-623
29. Frost JW, Draths KM (1995) Biocatalytic synthesis of aromatics from D-glucose: renewable microbial sources of aromatic compounds. Annu Rev Mircobiol 49:557-579
30. Frost JW, Snell KD, Frost KM (1998) Deblocking the common pathway of aromatic amino acid synthesis. US Patent no. US 5,776,736
31. Fukui S, Ikeda S, Fujimura M, Yamada H, Kumagai H (1975a) Comparative studies on properties of tryptophanase and tyrosine phenol-lyase immobilized directly on Sepharose or by use of Sepharose-bound pyridoxal 5′-phosphate. Eur J Biochem 51:155-164
32. Fukui S, Ikeda S, Fujimura M, Yamada H, Kumagai H (1975b) Production of L-tryptophan, L-tyrosine and their analogs by use of immobilized tryptophanase and immobilized beta-tyrosinase. Eur J Appl Microbiol 1:25-39
33. Garner CC, Herrmann KM (1985) Operator mutations of the Escherichia coli aroF gene. J Biol Chem 260:3820-3825
34. Gerth TD, Mann RW, Ayres JR (1999) Dietary supplement composition. US Patent no. US 5,925,377
35. Giovannini M, Verduci E, Salvatici E, Fiori L, Riva E (2007) Phenylketonuria: dietary and therapeutic challenges. J Inherit Metab Dis 30:145-152
36. Hagino H, Nakayama K (1973a) L-tyrosine production by analog-resistant prototrophic mutants of glutamic acid producing bacteria. Agric Biol Chem 37:2007-2011
37. Hagino H, Nakayama K (1973b) L-tyrosine production by analog-resistant mutants derived from a phenylalanine auxotroph of Corynebacterium glutamicum. Agric Biol Chem 37:2013-2023
38. Hagino H, Yoshida H, Kato F, Arai Y, Katsumata R, Nakayama K (1973) L-tyrosine production by polyauxotrophic mutants of Corynebacterium glutamicum. Agric Biol Chem 37:2001-2005
39. Hagino H, Nakayama K, Yoshida H (1974) Process for the production of L-tyrosine. US Patent no. US 3,787,287
40. Hatti-Kaul R, Törnvall U, Gustafsson L, Börjesson P (2007) Industrial biotechnology for the production of bio-based chemicals-a cradle-to-grave perspective. Trends Biotechnol 25:119-124
41. Herrmann KM (1995) The shikimate pathway: early steps in the biosynthesis of aromatic compounds. Plant Cell 7:907-919
42. Herrmann KM, Weaver LM (1999) The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 50:473-503
43. Hermann BG, Patel M (2007) Today's and tomorrow's bio-based bulk chemicals from white biotechnology. Appl Biochem Biotechnol 136:361-388
44. Ikeda M (2003) Amino acid production processes. In: Scheper T, Faurie R, Thommel J (eds) Advances in biochemical engineering/biotechnology, vol. 79. Springer, Berlin, pp 1-35
45. Ikeda M (2006) Towards bacterial strains overproducing L-tryptophan and other aromatics by metabolic engineering. Appl Microbiol Biotechnol 69:615-626
46. Ikeda M, Katsumata R (1992) Metabolic engineering to produce tyrosine or phenylalanine in a tryptophan-producing Corynebacterium glutamicum strain. Appl Environ Microbiol 58:781-785
47. Ikeda M, Katsumata R (1994) Transport of aromatic amino acids and its influence on overproduction of the amino acids in Corynebacterium glutamicum. J Ferment Bioeng 78:420-425
48. Ikeda M, Okamoto K, Katsumata R (1999) Cloning of the transketolase gene and the effect of its dosage on aromatic amino acid production in Corynebacterium glutamicum. Appl Microbiol Biotechnol 51:201-206
49. Ito H, Sakurai S, Tanaka T, Sato K, Enei H (1990a) Genetic breeding of L-tyrosine producer from Brevibacterium lactofermentum. Agric Biol Chem 54:699-705
50. Ito H, Sato K, Enei H, Hirose Y (1990b) Improvement in microbial production of L-tyrosine by gene dosage effect of aroL gene encoding shikimate kinase. Agric Biol Chem 54:823-824
51. Katsumata R, Ikeda M (1993) Process for producing L-tryptophan, L-tyrosine or L-phenylalanine. European patent EP 0600463B1
52. Kim JH, Song JJ, Kim BG, Sung MH, Lee SG (2004) Enhanced stability of tyrosine phenol-lyase from Symbiobacterium toebii by DNA shuffling. J Microbiol Biotechnol 14:153-157
53. Kim DY, Rha E, Choi SL, Song JJ, Hong SP, Sung MH, Lee SG (2007) Development of bioreactor system for L-tyrosine synthesis using thermostable tyrosine phenol-lyase. J Microbiol Biotechnol 17:116-122
54. Koffas M, del Cardayre S (2005) Evolutionary metabolic engineering. Metab Eng 7:1-3
55. Krämer R (1994) Secretion of amino acids by bacteria: physiology and mechanism. FEMS Microbiol Rev 13:75-94
56. Krämer M, Bongaerts J, Bovenberg R, Kremer S, Müller U, Orf S, Wubbolts M, Raeven L (2003) Metabolic engineering for microbial production of shikimic acid. Metab Eng 5:277-283
57. Kumagai H, Yamada H, Matsui H, Ohkishi H, Ogata K (1970) Tyrosine phenol lyase. I. Purification, crystallization, and properties. J Biol Chem 245:1767-72
58. Kyowa Hakko Kogyo (2006) Kyowa Hakko develops world's first commercial production method for L-tyrosine based on fermentation; successful mass production of L-tyrosine from non-animal sources. Press release, September 26, 2006
59. Lee TK, Hsiao HY (1986) Synthesis of L-tyrosine by a coupled reaction of serine hydroxymethyl-transferase and beta-tyrosinase. Enzyme Microb Technol 8:523-526
60. Leuchtenberger W (1996) Amino acids-technical production and use. In: Rehm H-J, Reed G, Pühler A, Stadler P (eds) Biotechnology. Products of primary metabolism, vol. 6. 2nd edn. VCH, Weinheim, pp 465-502
61. Leuchtenberger W, Huthmacher K, Drauz K (2005) Biotechnological production of amino acids and derivatives: current status and prospects. Appl Microbiol Biotechnol 69:1-8
62. Lloyd-George I, Chang TMS (1993) Free and microencapsulated Erwinia herbicola for the production of tyrosine. Biomater Artif Cells Immobil Biotechnol 21:323-33
63. Lloyd-George I, Chang TMS (1995) Characterization of free and alginate-polylysine-alginate microencapsulated Erwinia herbicola for the conversion of ammonia, pyruvate, and phenol into L-tyrosine. Biotechnol Bioeng 48:706-714
64. Lütke-Eversloh T, Stephanopoulos G (2005) Feedback inhibition of chorismate mutase/prephenate dehydrogenase (TyrA) of Escherichia coli: generation and characterization of tyrosine-insensitive mutants. Appl Environ Microbiol 71:7224-7228
65. Lütke-Eversloh T, Stephanopoulos G (2007a) L-Tyrosine production by deregulated strains of Escherichia coli. Appl Microbiol Biotechnol 75:103-110
66. Lütke-Eversloh T, Stephanopoulos G (2007b) Combinatorial pathway analysis for improved L-tyrosine production in Escherichia coli: identification of enzymatic bottlenecks by systematic aromatic amino acid biosynthesis gene overexpression. Metab Eng (submitted)
67. Lütke-Eversloh T, Stephanopoulos G (2007c) A semi-quantitative high-throughput screening method for microbial L-tyrosine production in microtiter plates. J Ind Microbiol Biotechnol, DOI 10.1007/s10295-007-0257-x
68. Mark AM (1939) Isolation of leucine and tyrosine from corn gluten. US Patent no. US 2,178,210
69. Nagasawa T, Utagawa T, Goto J, Kim CJ, Tani Y, Kumagai H, Yamada H (1981) Syntheses of L-tyrosine-related amino acids by tyrosine phenol-lyase of Citrobacter intermedius. Eur J Biochem 117:33-40
70. Neri DF, Wiegmann D, Stanny RR, Shappell SA, McCardie A, McKay DL (1995) The effects of tyrosine on cognitive performance during extended wakefulness. Aviat Space Environ Med 66:313-319
71. O'Brien C, Mahoney C, Tharion WJ, Sils IV, Castellani JW (2007) Dietary tyrosine benefits cognitive and psychomotor performance during body cooling. Physiol Behav 90:301-7
72. Oldiges M, Kunze M, Degenring D, Sprenger GA, Takors R (2004) Stimulation, monitoring, and analysis of pathway dynamics by metabolic profiling in the aromatic amino acid pathway. Biotechnol Prog 20:1623-1633
73. Olson MM, Templeton LJ, Suh W, Youderian P, Sariaslani FS, Gatenby AA, Van Dyk TK (2007) Production of tyrosine from sucrose or glucose achieved by rapid genetic changes to phenylalanine-producing Escherichia coli strains. Appl Microbiol Biotechnol 74:1031-1040
74. Para G, Lucciardi P, Baratti J (1985) Synthesis of L-tyrosine by immobilized Escherichia intermedia cells. Appl Microbiol Biotechnol 21:273-279
75. Patnaik R, Liao JC (1994) Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield. Appl Environ Microbiol 60:3903-3908
76. Patnaik R, Spitzer RG, Liao JC (1995) Pathway engineering for production of aromatics in Escherichia coli: confirmation of stoichiometric analysis by independent modulation of AroG, TktA and Pps activities. Biotech Bioeng 46:361-370
77. Phillips RS, Ravichandran K, Vontersch RL (1989) Synthesis of L-tyrosine from phenol and S-(ortho-nitrophenyl)-L-cysteine catalyzed by tyrosine phenol-lyase. Enzyme Microb Technol 11:80-83
78. Pittard J (1996) Biosynthesis of aromatic amino acids. In: Neidhardt FC (ed) Escherichia coli and Salmonella typhimurium: cellular and molecular biology, vol. 1. American Society of Microbiology, Washington, DC, pp 458-484
79. Pittard J, Camakaris H, Yang J (2005) The TyrR regulon. Mol Microbiol 55:16-26
80. Pohnert G, Zhang S, Husain A, Wilson DB, Ganem B (1999) Regulation of phenylalanine biosynthesis. Studies on the mechanism of phenylalanine binding and feedback inhibition in the Escherichia coli P-protein. Biochemistry 38:12212-12217
81. Polen T, Krämer M, Bongaerts J, Wubbolts M, Wendisch VF (2005) The global gene expression response of Escherichia coli to L-phenylalanine. J Biotechnol 115:221-237
82. Qi WW, Sariaslani S, Tang XS (2002). Methods for the production of tyrosine, cinnamic acid and para-hydroxycinnamic acid. World Patent no. WO 02/090523
83. Qi WW, Vannelli T, Breinig S, Ben-Bassat A, Gatenby AA, Haynie SL, Sariaslani FS (2007) Functional expression of prokaryotic and eukaryotic genes in Escherichia coli for conversion of glucose to p-hydroxystyrene. Metab Eng 9:268-76
84. Rajput A, Rajput AH (2006) Parkinson's disease management strategies. Expert Rev Neurother 6:91-99
85. Rohr FJ, Lobbregt D, Levy HL (1998) Tyrosine supplementation in the treatment of maternal phenylketonuria. Am J Clin Nutr 67:473-476
86. Roy A, Mukhopadhyay SK, Chatterjee SP (1997) Production of tyrosine by auxotrophic and analogue resistant mutants of Arthrobacter globiformis. J Sci Ind Res 56:727-733
87. Santos CNS, Stephanopoulos G (2007) Methods for identifying bacterial strains that produce L-tyrosine. US patent application no. 60/965,149
88. Sariaslani FS (2007) Development of a combined biological and chemical process for production of industrial aromatics from renewable resources. Annu Rev Microbiol 61:51-69
89. Snell KD, Draths KM, Frost JW (1996) Synthetic modification of the Escherichia coli chromosome: enhancing the biocatalytic conversion of glucose into aromatic chemicals. J Am Chem Soc 118:5605-5614
90. Sprenger GA (2007a) Aromatic amino acids. In: Wendisch VF (ed) Amino acid biosynthesis-pathways, regulation and metabolic engineering. Microbiology Monographs series, vol. 5. Springer, Berlin, pp 93-127 (Steinbüchel A, series editor)
91. Sprenger GA (2007b) From scratch to value: engineering Escherichia coli wild type cells to the production of L-phenylalanine and other fine chemicals derived from chorismate. Appl Microbiol Biotechnol 75:739-749
92. Steinmetzer W (1983) Process for recovering amino acids from protein hydrolysates. US Patent no. US 4,384,136
93. Stephanopoulos G, Sinskey AJ (1993) Metabolic engineering: issues and methodologies. Trends Biotechnol 11:392-396
94. Stephanopoulos G, Simpson TW (1997) Flux amplification in complex metabolic networks. Chem Eng Sci 52:2607-2627
95. Stephanopoulos G, Kelleher J (2001) How to make a superior cell. Science 292:2024-2026
96. Sugimoto S, Shiio I (1980) Purification and properties of bifunctional 3-deoxy-D-arabino-heptulosonate 7-phosphate synthasechorismate mutase component A from Brevibacterium flavum. J Biochem 87:881-890
97. Takai A, Nishi R, Joe Y, Ito H (2005) L-Tyrosine producing bacterium and a method for producing L-tyrosine. US Patent application no. 2005/0277179 A1
98. Tanaka K, Ohshima K, Tokoro Y, Okii M (1972) Preparation of L-tyrosine by fermentation. US Patent no. US 3,698,997
99. Tribe DE (1987) Novel microorganism and method. US Patent no. US 4,681,852
100. Tyo KE, Alper HS, Stephanopoulos GN (2007) Expanding the metabolic engineering toolbox: more options to engineer cells. Trends Biotechnol 25:132-137
101. Tysyachnaya IV, Yakovleva VI, Kupletskaya MB, Berezin IV (1979) Kinetic study of tyrosine synthesis in tyrosine phenol lyase reaction catalyzed by Citrobacter freundii cells. Biochemistry (Moscow) 44:1739-1744
102. van Spronsen FJ, van Rijn M, Bekhof J, Koch R, Smit PG (2001) Phenylketonuria: tyrosine supplementation in phenylalanine-restricted diets. Am J Clin Nutr 73:153-7
103. Vannelli T, Qi WW, Sweigard J, Gatenby AA, Sariaslani FS (2007) Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metab Engin 9:142-151
104. Vassel B (1956) Separation of tyrosine. US Patent no. US 2,738,366
105. Williams M (2005) Dietary supplements and sports performance: amino acids. J Int Soc Sports Nutr 2:63-67
106. Yamada H, Kumagai H, Kashima N, Torii H, Enei H, Okumura S (1972) Synthesis of L-tyrosine from pyruvate, ammonia and phenol by crystalline tyrosine phenol lyase. Biochem Biophys Res Commun 46:370-374
107. Yi J, Draths KM, Li K, Frost JW (2003) Altered glucose transport and shikimate product yields in Escherichia coli. Biotechnol Prog 19:1450-1459