Synthetic modification of the Escherichia coli chromosome: Enhancing the biocatalytic conversion of glucose into aromatic chemicals

Journal of the American Chemical Society

Volumn 118, Issue 24, 1996, Pages 5605-5614

  Snell, K D ^a,b   Draths, K M ^a   Frost, J W ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATROLACTIC ACID; PHENYLALANINE;

ARTICLE; CATALYSIS; DNA MODIFICATION; ENZYME ACTIVITY; ESCHERICHIA COLI; MUTATION;

EID: 0030017232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9538041     Document Type: Article

References (80)

1. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
2. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
3. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
4. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
5. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
6. For relevant reviews of biosynthesis of aromatics, see: (a) Campbell, M. M.; Sainsbury, M.; Searle, P. A. Synthesis 1993, 179. (b) Haslam, E. Shikimic Acid: Metabolism and Metabolites; Wiley: New York, 1993. (c) Dewick, P. M. Nat. Prod. Rep. 1992, 9, 153. (d) Bentley, R. Crit. Rev. Biochem. Mol. Biol. 1990, 25, 307. (e) The Shikimate Pathway; Conn, E. E., Ed.; Plenum: New York, 1986. (f) Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds; Wiley: New York, 1980.
7. (a) Cobbett, C. S.; Morrison, S.; Pittard, J. J. Bacteriol. 1984, 157, 303.
8. (b) Garner, C. C.; Herrmann, K. M. J. Biol. Chem, 1985, 260, 3820.
9. (c) Cobbett, C. S.; Delbridge, M. L. J. Bacteriol. 1987, 169, 2500.
10. (d) Ogino, T.; Garner, C.; Markley, J. L.; Herrmann, K. M. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 5828.
11. (e) Weaver, L. M.; Herrmann, K. M. J. Bacteriol. 1990, 172, 6581.
12. (a) Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1990, 112, 1657.
13. (b) Draths, K. M.; Pompliano, D. L.; Conley, D. L.; Frost, J. W.; Berry, A.; Disbrow, G. L.; Staversky, R. J.; Lievense, J. J. Am. Chem. Soc. 1992, 114, 3956.
14. (c) Frost, J. W. U.S. Patent 5 168056, 1992.
15. (d) Draths, K. M. Ph.D. Thesis, Stanford University, July 1991.
16. (a) Patnaik, R.; Liao, J. C. Appl. Environ. Microbiol. 1994, 60, 3903.
17. (b) Patnaik, R.; Spitzer, R. G.; Liao, J. C. Biotechnol. Bioeng. 1995, 46, 361.
18. (a) Miller, J. E.; Backman, K. C.; O'Connor, M. J.; Hatch, R. T. J. Ind. Microbiol. 1987, 2, 143.
19. (b) Backman, K. C. U. S. Patent 5 169 768, 1992.
20. (a) Dell, K. A.; Frost, J. W. J. Am. Chem. Soc. 1993, 115, 11581.
21. (b) Dell, K. A. Ph.D. Thesis. Purdue University, December 1993.
22. Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1990, 112, 9630.
23. (a) Matsui, K.; Miwa, K.; Sano, K. U.S. Patent 5017 481, 1991.
24. (b) Tribe, D. E. U.S. Patent 4 681 852, 1987.
25. (a) Pittard, A. J. In Esrherichia coli and Salmonella typhimurium; Neidhardt, F. C., Ed.; American Society for Microbiology: Washington, DC, 1987; Vol. 1. p 368.
26. (b) Herrmann, K. M. In Amino Acids: Biosynthesis and Genetic Regulation; Herrmann, K. M., Somerville, R. L., Eds.; Addison-Wesley: Reading, 1983; p 301.
27. Mascarenhas, D.; Ashworth, D. J.; Cher, C. S. Appl. Environ. Microbiol. 1991, 57, 2995.
28. Shultz, J.; Hermodson, M. A.; Garner, C. C.; Herrmann, K. M. J. Biol. Chem. 1984, 259, 9655.
29. (a) Sprenger, G. A. J. Bacteriol. 1992, 174, 1707.
30. (b) Sprenger, G. A. Biochim. Biophys. Acta 1993, 1216, 307.
31. Berlyn, M. B.; Giles, N. H. J. Bacteriol. 1969, 99, 222.
32. (a) DeFeyter, R. C.; Pittard, J. J. Bacteriol. 1986, 165, 331.
33. (b) DeFeyter, R. C.; Davidson, B. E.; Pittard, J. J. Bacteriol. 1986, 165, 233.
34. (c) DeFeyter, R. C.; Pittard, J. J. Bacteriol. 1986, 165, 226.
35. Løbner-Olesen, A.; Marinus, M. G. J. Bacteriol. 1992, 174, 525.
36. Ely, B.; Pittard, J. J. Bacteriol. 1979, 138, 933.
37. Muday, G. K.; Johnson, D. I.; Somerville, R. L.; Herrmann, K. M. J. Bacteriol. 1991, 173, 3930.
38. Duncan, K.; Coggins, J. R. Biochem. J. 1986, 234, 49.
39. (a) deBoer, H. A.; Comstock, L.; Yasser, M. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 21.
40. (b) Amann, E.; Brosius, J.; Ptashne, M. Gene 1983, 25, 167.
41. (a) Mullis, K. B.; Faloona, F. A. Methods Enzymol. 1987, 155, 335.
42. (b) Erlich, H. Polymerase Chain Reaction; Cold Spring Harbor: Plainview, NY, 1989.
43. Duncan, K.; Lewendon, A.; Coggins, J. R. FEBS Lett. 1984, 170, 59.
44. (a) White, P. J.; Millar, G.; Coggins, J. R. Biochem. J. 1988, 251, 313.
45. (b) Charles, I. G.; Lamb, H. K.; Pickard, D.; Dougan, G.; Hawkins, A. R. J. Gen. Microbiol. 1990, 136, 353.
46. Millar, G.; Coggins, J. R. FEBS Lett. 1986, 200, 11.
47. Bartolomé, B.; Jubele, Y.; Martinez, E.; de la Cruz, F. Gene 1991, 102, 75.
48. Short, J. M.; Fernandez, J. M.; Sorge, J. A.; Huse, W. D. Nucleic Acids. Res. 1988, 16, 7583.
49. Pillard, J.; Wallace, B. J. J. Bacteriol. 1966, 91, 1494.
50. Lerner, C. G.; Inouye, M. Nucleic Acids Res. 1990, 18, 4631.
51. Davis, B. D. Science 1953, 118, 251.
52. Hamilton, C. M.; Aldea, M.; Washburn, B. K.; Babitzke, P.; Kushner, S. R. J. Bacteriol. 1989, 171, 4617.
53. Rex, J. H.; Aronson, B. D.; Somerville, R. L. J. Bacteriol. 1991, 173, 5944.
54. Ohta, K.; Beall, D. S.; Mejia, J. P.; Shanmugam, K. T.; Ingram, L. O. Appl. Environ. Microbiol. 1991, 57, 893.
55. Boocock, M. R.; Coggins, J. R. FEBS Lett. 1983, 154, 127.
56. (a) Addadi, L.; Jaffe, E. K.; Knowles, J. R. Biochemistry 1983, 22, 4494.
57. (b) Copley, S. D.; Knowles, J. R. J. Am. Chem. Soc. 1987, 109, 5008.
58. Weiss, U.; Gilvarg, C.; Mingioli, E. S.; Davis, B. D. Science 1954, 119, 774.
59. Kim, M-J.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 2959.
60. Frost, J. W.; Lievense, J. New J. Chem. 1994, 18, 341.
61. Hirschbein, B. L.; Mazenod, F. P.; Whitesides, G. M. J. Org. Chem. 1982, 47, 3765.
62. Frost, J. W.; Knowles, J. R. Biochemistry 1984, 23, 4465.
63. Reimer, L. M.; Conley, D. L.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1986, 108, 8010.
64. (a) Knowles, P. F.; Levin, J. G.; Sprinson, D. B. Methods Enzymol. 1971, 17A, 360.
65. (b) Levin, J. G.; Sprinson, D. B. J. Biol. Chem. 1964, 239, 1142.
66. Miller, J. H. Experiments in Molecular Genetics; Cold Spring Harbor Laboratory: Plainview, NY, 1972.
67. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A Laboratory Manual; Cold Spring Harbor Laboratory: Plainview, NY, 1990.
68. Millar, G.; Anton, I. A.; Mousdale, D. M.; White, P. J.; Coggins, J. R. Biochem. Soc. Trans. 1986, 14, 262.
69. Frost, J. W.; Bender, J. L.; Kadonaga, J. T.; Knowles, J. R. Biochemistry 1984, 23, 4470.
70. Oka, A.; Sugisaki, H.; Takanami, M. J. Mol. Biol. 1981, 147, 217.
71. Amann, E.; Ochs, B.; Abel, K.-J. Gene 1988, 69, 301.
72. Russell, D. R.; Bennett, G. N. Gene 1982, 20, 231.
73. Tsang, T.; Copeland, V.; Bowden, G. T. Biotechniques 1991, 10, 330.
74. Balbas, P; Soberon, X.; Merino, E.; Zurita, M.; Lomeli, H.; Valle, F.; Flores, N.; Bolivar, F. Gene 1986, 50, 3.
75. Silhavy, T. J.; Berman, M. L.; Enquist, L. W. Experiments with Gene Fusions; Cold Spring Harbor Laboratory: Plainview, NY, 1984.
76. Feinberg, A. P; Vogelstein, B. Anal Biochem. 1983, 132, 6.
77. Bradford, M. M. Anal. Biochem. 1976, 72, 248.
78. Gollub, E.; Zalkin, H.; Sprinson, D. B. Methods Enzymol. 1971, 17A, 349.
79. DeFeyter, R. Methods Enzymol. 1987, 142, 355.
80. Morell, H; Clark, M. J.; Knowles, P. F.; Sprinson, D. B. J. Biol. Chem. 1967, 242, 82.