The catabolism of phenylacetic acid and other related molecules in pseudomonas putida U

Pseudomonas

Volumn 5, Issue , 2007, Pages 147-192

  Luengo, José M ^a   Arias, Sagrario ^a   Arcos, Mario ^a   Olivera, Elías R ^a  

^a UNIVERSITY OF LEÓN   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880926632     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4020-6097-7_6     Document Type: Chapter

References (129)

1. Abe-Yoshizumi, R., Kamei, U., Yamada, A., Kimura, M., and Ichihara, S., 2004, The evolution of the phenylacetic acid degradation pathway in bacteria. Biosci. Biotechnol. Biochem., 68:746-748.
2. Abraham, G., Gallardo., A., San Román, J., Olivera, E. R., Jodrá, R., García, B., Miñambres, B., García, J.L., and Luengo, J.M., 2001, Microbial synthesis of poly(β- hydroxyalkanoates) bearing phenyl groups from Pseudomonas putida: chemical structure and characterization. Biomacromolecules, 2:562-567.
3. Alexander, M., 1981, Biodegradation of chemicals of environmental concern. Science, 221:132-138.
4. Altenschmidt, U., and Fuchs, G., 1992, Novel aerobic 2-aminobenzoate metabolism. Purification and characterization of 2-aminobenzoate-CoA ligase, location of the gene on a 8-kbp plasmid, and cloning and sequencing of the gene from a denitrifying Pseudomonas sp. Eur. J. Biochem., 205:721-727.
5. Altenschmidt, U., Oswald, B., Steiner, E., Hermann, H., and Fuchs, G., 1993, New aerobic benzoate oxidation pathway via benzoyl-coenzyme A and 3-hydroxybenzoyl-coenzyme A in a denitrifying Pseudomonas sp. J. Bacteriol., 175:4851-4858.
6. Anders, A., Kaetzke, A., Kämpfer, P., Ludwig, W., and Fuchs, G., 1995, Taxonomic position of aromatic degrading denitrifying pseudomonas strains K172 and KB740 and their description as new members of the genera Thauera, T. aromatica sp. nov., and Azoarcus, A. evansii sp., nov., respectively, members of the beta subclass of Proteobacteria. Int. J. Syst. Bacteriol., 45:327-333.
7. Anderson, J.J., and Dagley, S., 1980, Catabolism of aromatic acids in Trichosporon cutaneum. J. Bacteriol., 141:534-543.
8. Arias-Barrau, E., Sandoval, A., Naharro, G., Olivera, E.R., and Luengo, J.M., 2005, A two-component hydroxylase involved in the assimilation of 3-hydroxyphenylacetate in Pseudomonas putida. J. Biol. Chem., 280:26435-26447.
9. Arias-Barrau, E., Olivera, E.R., Luengo, J.M., Fernández, C., Galán, B., García, J.L., Díaz, E., and Miñambres, B., 2004, The homogentisate pathway: A central catabolic pathway involved in the degradation of L-phenylalanine, L-tyrosine and 3-hydroxyphenylacetate in Pseudomonas putida. J. Bacteriol., 186:5062-5077.
10. Arunachalam, U., Massey, V., and Vaidyanathan, C.S., 1992, p-Hydroxyphenylacetate- 3-hydroxylase. A two-protein component enzyme. J. Biol. Chem., 267:25848-25855.
11. Auburger, G., and Winter, J., 1992, Purification and characterization of benzoyl-CoA ligase from a syntrophic, benzoate-degrading, anaerobic mixed culture. Appl. Microbiol. Biotechnol., 37:789-795.
12. Baev, N., Schultze, M., Barlier, I., Cam Ha, D., Virelizier, H., Kondorosi, E., and Kondorosi, A., 1992, Rhizobium nodM and nodN genes are common nod genes: nodM encodes functions for efficiency of Nod signal production and bacteroid maturation. J. Bacteriol., 174:7555-7565.
13. Bartolomé-Martín, D., Martínez-García, E., Mascaraque, V., Rubio, J., Perea, J., and Alonso, S., 2004, Characterization of a second functional gene cluster for the catabolism of phenylacetic acid in Pseudomonas sp. strain Y2. Gene, 341:167-179.
14. Blakley, E.R., Halvorson, H., and Kurz, W., 1967, The microbial production and some characteristics of ?-carboxymethyl semialdehyde. Can. J. Microbiol., 13:159-165.
15. Blakley, E.R., Kurz, W., Halvorson, H., and Simpson, F.J., 1967, The metabolism of phenylacetic acid by a Pseudomonas. Can. J. Microbiol., 13:147-157.
16. Cases, I., and De Lorenzo, V., 2005, Genetically modified organisms for the environment: Stories of success and failure and what we have learned from them. Int. Microbiol., 8:213-222.
17. Dagley, S., 1971, Catabolism of aromatic compounds by microorganisms. Adv. Microbiol. Physiol., 6:1-46.
18. Dagley, S., 1986, Biochemistry of aromatic hydrocarbon degradation in Pseudomonas, pp. 527-556. In I.C. Gunsalus, J.R. Sokatch, and L.N. Orston (eds.), The Bacteria, Vol. 10. Academic Press, New York.
19. Dagley, S., 1981, New perspectives in aromatic catabolism, pp. 181-186. In T. Leisinger, A.M. Cook, R. Hütter and J. Nüesch (eds.), Degradation of Xenobiotics and Recalcitrant Compounds. Academic Press, New York.
20. de Lorenzo, V., and Timmis, K.N., 1994, Analysis and construction of stable phenotypes in gram-negative bacteria with Tn5 and Tn10-derived minitransposons. Methods Enzymol., 235:386-405.
21. Demain, A.L., 1992, Microbial secondary metabolism: A new theoretical frontier for academia, a new opportunity for industry. Ciba Found. Symp., 171:3-16.
22. Díaz, E., 2004, Bacterial degradation of aromatic pollutants: A paradigm of metabolic versatility. Int. Microbiol., 7:173-180.
23. Díaz, E., Ferrández, A., Prieto, M.A., and García, J.L., 2001, Biodegradation of aromatic compounds in E. coli. Microbiol. Mol. Biol. Rev., 65:523-569.
24. Dolfing, J., Zeyer, P., Binder-Eicher, P., and Schwarzenbach, R.P., 1990, Isolation and characterization of a bacterium that mineralizes toluene in the absence of molecular oxygen. Arch. Microbiol., 155:256-262.
25. Evans, W.C., 1977, Biochemistry of the bacterial catabolism of aromatic compounds in anaerobic environment. Nature, 270:17-22.
26. Evans, W.C., and Fuchs, G., 1988, Anaerobic degradation of aromatic compounds. Annu. Rev. Microbiol., 42:289-317.
27. Eyers, L., George, I., Schuler, L., Stenuit, B., Agathos, S.N., and El Fantroussi, S., 2004, Environmental genomics: exploring the unmined richness of microbes to degrade xenobiotics. Appl. Microbiol. Biotechnol., 66:123-130.
28. Fernández, C., 2005, Avances en la Caracterización del Catabolismo del ácido Fenilacético en Escherichia coli. Tesis Doctoral. Universidad Complutense de Madrid.
29. Fernández-Cañón, J.M., Reglero, A., Martínez-Blanco, H., and Luengo, J.M., 1989, I. Uptake of phenylacetic acid by Penicillium chrysogenum Wis 54-1255. A critical regulatory point in the biosynthesis of benzylpenicillin. J. Antibiotics, 42:1398-1409.
30. Fernández-Cañón, J.M., and Luengo, J.M., 1997, The phenylacetic acid uptake system of Aspergillus nidulans is under a creA-independent model of catabolic repression which seems to be mediated by acetyl-CoA. J. Antibiotics, 50:45-52.
31. Fernández-Valverde, M., Reglero, A., Martínez-Blanco, H., and Luengo, J.M., 1993, Purification of Pseudomonas putida acyl coenzyme A ligase active with a range of aliphatic and aromatic substrates. Appl. Environ. Microbiol., 59:1149-1154.
32. Ferrández, A., García, J.L., and Díaz, E., 2000, Transcriptional regulation of the divergent PhAc catabolic operons for phenylacetic acid degradation. J. Biol. Chem., 275:12214-12222.
33. Ferrández, A., Miñambres, B., García, B., Olivera, E.R., Luengo, J.M., García, J.L., and Díaz, E., 1998, Catabolism of phenylacetic acid in Escherichia coli. Characterization of a new aerobic hybrid pathway. J. Biol. Chem., 273:25974-25986.
34. Ferrández, A., Prieto, M.A., García J.L., and Díaz, E., 1997, Molecular characterization of PadA, a phenylacetaldehyde dehydrogenase from Escherichia coli. FEBS Lett., 406:23-27.
35. Fewson, C.A., 1988, Microbial metabolism of mandelate a microcosm of diversity. FEMS Microbiol. Rev., 54:85-110.
36. Fuchs, G., Mohamed, M.E., Altenschmidt, U., Koch, J., Lack, A., Brackmann, R., Lochmeyer, C., and Oswald, B., 1994, Biochemistry of anaerobic degradation of aromatic compounds, pp. 513-553. In C. Ratledge (ed.), Biochemistry of Microbial Degradation. Kluwer Academic Press, Dordrecht.
37. Gagné, F., Blaise, C., and André, C., 2006, Occurrence of pharmaceutical products in a municipal effluent and toxicity to rainbow trout (Oncorhynchus mykiss) hepatocytes. Ecotox. Environ. Saf., 143:179-186.
38. Galán, B., García, J.L., and Prieto, M.A., 2004, The PaaX repressor, a link between penicillin G acylase and the phenylacetyl-Coenzyme A catabolon of Escherichia coli W. J. Bacteriol., 186:2215-2220.
39. Galvao, T.C., Mohn, W.W., and de Lorenzo, V., 2005, Exploring the microbial biodegradation and biotransformation gene pool. Trends Biotechnol., 23:497-506.
40. García, B., Olivera, E.R., Miñambres, B., Carnicero, D., Muñiz, C., Naharro, G., and Luengo, J.M., 2000, Phenylacetyl-coenzyme A is the true inducer of the phenylacetic acid catabolism pathway in Pseudomonas putida U. Appl. Environ. Microbiol., 66:4575-4578.
41. García, B., Olivera, E.R., Miñambres, B., Fernández-Valverde, M., Cañedo, L.M., Prieto, M.A., García, J.L., Martínez, M., and Luengo, J.M., 1999, Novel biodegradable aromatic plastics from a bacterial source. Genetic and biochemical studies on a route of the phenylacetyl-CoA catabolon. J. Biol. Chem., 274:29228-29241.
42. Geissler, J.F., Harwood, C.S., and Gibson, J., 1988, Purification and properties of benzoate- coenzyme A ligase, a Rhodopseudomonas palustris enzyme involved in the anaerobic degradation of benzoate. J. Bacteriol., 170:1709-1714.
43. Gibson, J., Geissler, J.F., and Harwood, C.S., 1990, Benzoate-coenzyme A ligase from Rhodopseudomonas palustris. Methods Enzymol., 188:154-159.
44. Gibson, D.T., and Subramanian, V., 1984, Microbial degradation of aromatic hydrocarbons, pp. 181-252. In D.T. Gibson (ed.), Microbial Degradation of Organic Compounds. Marcel Dekker, New York.
45. Gulick, A.M., Starai, V.J., Horswill, A.R., Homick, K.M., and Scalante-Semerena, J.C., 2003, The 1.75 Å crystal structure of acetyl-CoA synthetase bound to adenosine-5′- propylphosphate and coenzyme A. Biochemistry, 42:2866-2873.
46. Harayama, S., Kok, M., and Neidle, E.L., 1992, Functional and evolutionary relationship among diverse oxygenases. Annu. Rev. Microbiol., 46:565-601.
47. Harayama, S., and Timmis, K.N., 1989, Catabolism of aromatic hydrocarbons by Pseudomonas, pp. 151-174. In D. Hopwood and K. Chater, (eds.), Genetic of Bacterial Diversity. Academic Press, London.
48. Harayama, S., and Timmis, K.N., 1992, Aerobic degradation of aromatic hydrocarbons by bacteria, pp. 99-156. In H. Sigel and A. Sigel (eds.), Degradation of Environmental Pollutants by Microorganisms and Their Metalloenzymes. Metal Ions in Biological Systems, Vol. 28. Marcel Dekker, New York.
49. Harwood, C.S., and Gibson, J., 1988, Anaerobic and aerobic metabolism of diverse aromatic compounds by the photosynthetic bacterium Rhod opseudomonas palustris. Appl. Environ. Microbiol., 54:712-717.
50. Harwood, C.S., and Parales, R.E., 1996, The β-ketoadipate pathway and the biology of self-identity. Annu. Rev. Microbiol., 50:553-590.
51. Heider, J., and Fuchs, G., 1997, Anaerobic metabolism of aromatic compounds. Eur. J. Biochem., 243:577-596.
52. He, X.-Y., Deng, H., and Yang, S.-Y., 1997, Importance of the gamma-carboxyl group of glutamate-462 of the large alpha-subunit for the catalytic function and the stability of the multienzyme complex of fatty acid oxidation from Escherichia coli. Biochemistry, 36:261-268.
53. Hess, A., Zarda, B., Hahn, D., Häner, A., Stax, D., Höhener, P., and Zeyer, J., 1997, In situ analysis of denitrifying toluene- And m-xylene-degrading bacteria in a diesel fuelcontaminated laboratory aquifer column. Appl. Environ. Microbiol., 63:2136-2141.
54. Ismail, W., Mohamed, M.E., Wanner, B.L., Datsenko, K.A., Eisenreich, W., Rohdich, F., Bacher, A., and Fuchs, G., 2003, Functional genomics by NMR spectroscopy. Phenylacetate catabolism in Escherichia coli. Eur. J. Biochem., 270:3047-3054.
55. Jenner, A.M., Rafter, M., and Halliwell, B., 2005, Human fecal water content phenolics: The extent of colonic exposure to aromatic compounds. Free Radic. Biol. Med., 38:763-772.
56. Jiménez, J.J., Miñambres, B., García, J.L., and Díaz, E., 2002, Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440. Environ. Microbiol., 4:824-841.
57. Jogl, G., and Tong, L., 2004, Crystal structure of yeast acetyl-coenzyme A synthetase in complex with AMP. Biochemistry, 43:1425-1431.
58. Keith, L.H., and Teillard, W.A., 1979, Prioritary pollutants I- A perspective view. Environ. Sci. Tecnol., 13:416-423.
59. Kreusch, A., Neubuser, A., Schiltz, E., Weckesser, J., and Schulz, G.E., 1994, Structure of the membrane channel porin from Rhodopseudomonas blastica at 2.0 Å resolution. Protein Sci., 3:58-63.
60. Kaschabek, S.R., Kuhn, B., Müller, D., Schmidt, E., and Reineke, W., 2002, Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: Purification and characterization of 3-oxoadipate:succinyl-CoA thiolas . J. Bacteriol., 184:207-215.
61. Löffler, F., Müller, R., and Lingens, F., 1992, Purification and properties of 4-halobenzoate- coenzyme A ligase from Pseudomonas sp. CBS3. Biol. Chem. Hoppe-Seyler, 373:1001-1007.
62. Long, M.T., Bartholomew, B.A., Smith, M.J., Trudgill, P.W., and Hopper, D.J., 1997, Enzymology of oxidation of tropic acid to phenylacetic acid in metabolism of atropine by Pseudomonas sp. strain AT3. J. Bacteriol., 179:1044-1050.
63. Lovley, D.R., Woodward, J.C., and Chapelle, F.H., 1994, Stimulated anoxic biodegradation of aromatic hydrocarbons using Fe(III) ligands. Nature, 370:128-131.
64. Luengo, J.M., 1998, Enzymatic synthesis of penicillins, pp. 239-274. In D. Barton, K. Nakanishi, and O. Meth-Cohn (eds.), Amino Acids, Peptides, Porphyrins, and Alkaloids. Comprehensive Natural Products Chemistry, Vol. 4. Pergamon, Amsterdam.
65. Luengo, J.M., Arias, S., Sandoval, A., Arias-Barrau, E., Arcos, M., Naharro, G., and Olivera, E.R., 2004, From aromatics to bioplastics: The phenylacetyl-CoA catabolon as a model of catabolic convergence, pp. 257-292. In A. Gayathri (ed.), Recent Research Developments in Biophysic and Biochemistry, Vol 4. Research Signpost, Kerala, India.
66. Luengo, J.M., García, J.L., and Olivera, E.R., 2001, The phenylacetyl-CoA catabolon: A complex catabolic unit with broad biotechnological applications. Mol. Microbiol., 39:1434-1442.
67. Luengo, J.M., García, B., Sandoval, A., Arias-Barrau, E., Arias, S., Bermejo, F., and Olivera, E.R., 2004, The phenylacetyl-CoA catabolon. Genetic, biochemical and biotechnological approaches, pp. 91-129. In J.L. Barredo (ed.), Microbial Processes and Products. Methods in Biotechnology, Vol. 18. Humana Press, Inc. Totowa, NJ.
68. Luengo, J.M., García, B., Sandoval, A., Naharro, G., and Olivera, E.R., 2003, Bioplastics from microorganisms. Curr. Opin. Microbiol., 6:251-260.
69. Martínez-Blanco, H., Reglero, A., and Luengo, J.M., 1990, Carbon catabolite regulation of phenylacetyl-CoA ligase from P. putida. Biochem. Biophys. Res. Commun., 167:891-897.
70. Martínez-Blanco, H., Reglero, A., Rodríguez-Aparicio, L.B., and Luengo, J.M., 1990, Purification and biochemical characterization of phenylacetyl-CoA ligase from Pseudomonas putida. A specific enzyme for the catabolism of phenylacetic acid. J. Biol. Chem., 265:7084-7090.
71. Meyer, J.E., Hofnung, M., and Schulz, G.E., 1997, Structure of maltoporin from Salmonella typhimurium ligated with a nitrophenyl-maltosa. J. Mol. Biol., 266:761-775.
72. Miñambres, B., Martínez-Blanco, H., Olivera, E.R., García, B., Díez, B., Barredo, J.L., Moreno, M.A., Schleissner, C., Salto, F., and Luengo, J.M., 1996, Molecular cloning and expression in different microbes of the DNA encoding Pseudomonas putida U phenylacetyl-CoA ligase. Use of this gene to improve the rate of benzylpenicillin biosynthesis in Penicillium chrysogenum. J. Biol. Chem., 271:33531-33538.
73. Mohamed, M.E., 2000, Biochemical and molecular characterization of phenylacetate- CoA ligase, an enzyme catalyzing the first step in aerobic metabolism of phenylacetic acid in Azoarcus evansii. J. Bacteriol., 182:286-294.
74. Mohamed, M.E., and Fuchs, G., 1993, Purification and characterization of phenylacetate- coenzyme A ligase from a denitrifying Pseudomonas sp., an enzyme involved in the anaerobic degradation of phenylacetate. Arch. Microbiol., 159:554-562.
75. Mohamed, M.E., Ismail, W., Heider, J., and Fuchs, G., 2002, Aerobic metabolism of phenylacetic acids in Azoarcus evansii. Arch. Microbiol., 178:180-192.
76. Navarro-Llorens, J.M., Patrauchan, M.A., Stewart, G.R., Davies, J.E., Eltis, L.D., and Mohn, W.W., 2005, Phenylacetate catabolism in Rhodococcus sp. strain RHA1: A central pathway for the degradation of aromatic compounds. J. Bacteriol., 187:4497-4504.
77. Nikaido, H., 1992, Porins and specific channels of bacterial outer membranes. Mol. Microbiol., 6:435-442.
78. Nogales, J., Macchi, R., Franchi, F., Barzaghi, D., Fernández, C., García, J.L., Bertoni, G., and Díaz, E., 2006, Characterization of the last step of the aerobic phenylacetic acid degradation pathway (submitted).
79. Olivera, E.R., Carnicero, D., García, B., Miñambres, B., Moreno, M.A., Cañedo, L., Dirusso, C.C., Naharro, G., and Luengo, J.M., 2001, Two different pathways are involved in the β-oxidation of n-alkanoic acids in Pseudomonas putida U: genetic studies and biotechnological applications. Mol. Microbiol., 39:863-874.
80. Olivera, E.R., Carnicero, D., Jodra, R., Miñambres, B., García, B., Abraham, G.A., Gallardo, A., San Román, J., García, J.L., Naharro, G., and Luengo, J.M., 2001, Genetically engineered Pseudomonas: A factory of new bioplastics with broad applications. Environ. Microbiol., 3:612-618.
81. Olivera, E.R., Miñambres, B., García, B., Muñiz, C., Moreno, M.A., Ferrández, A., Díaz, E., García, J.L., and Luengo, J.M., 1998, Molecular characterization of the phenylacetic acid catabolic pathway in Pseudomonas putida U: The phenylacetyl-CoA catabolon. Proc. Natl Acad. Sci. USA, 95:6419-6424.
82. Olivera, E.R., Reglero, A., Martínez-Blanco, H., Fernández-Medarde, A., Moreno, M.A., and Luengo, J.M., 1994, Catabolism of aromatics in Pseudomonas putida U: Formal evidence that phenylacetic acid and 4-hydroxyphenylacetic acid are catabolized by two different pathways. Eur. J. Biochem., 221:375-381.
83. Paetsh, P.R., and Grewnshaw, A.J., 1993, 2-Phenyletylamine-induced changes in catecholamine receptor density: implications for antidepressant drug action. Neurochem. Res., 18:1015-1022.
84. Panke, S., de Lorenzo, V., Kaiser, A., Witholt, B., and Wubbolts, M.G., 1999, Engineering of a stable whole-cell biocatalyst capable of (S)-styrene oxide formation for continous two-liquid-phase applications. Appl. Environ. Microbiol., 65:5619-5623.
85. Parales R.E., and Haddock, J.D., 2004, Biocatalytic degradation of pollutants. Curr. Opin. Biotechnol., 15:374-379.
86. Paul, D., Pandey, G., Pandey, J., and Jain, R.K., 2005, Accessing microbial diversity for bioremediation and environmental restoration. Trends Biotechnol., 23:135-142.
87. Peso-Santos, T., Bartolomé-Martín, D., Fernández, C., Alonso, S., García, J.L., Díaz, E., Shingler, V., and Perera, J., 2006, Co-regulation through phenylacetyl-CoA responsive PaaX integrates control of the upper and lower pathways for catabolism of styrene by Pseudomonas sp. strain Y2. J. Bacteriol., 188:4812-4821.
88. Pieper, D.H., Martins dos Santos, V.A., and Golyshin, P.N., 2004, Genomic and mechanistic insights into the biodegradation of organic pollutants. Curr. Opin. Biotechnol., 15:215-24.
89. Poolea, A.J., and Cord-Ruwischb, R., 2004, Treatment of strong flow wool scouring effluent by biological emulsion destabilisation. Water Res., 38:1419-1426.
90. Prieto, M.A., Galán, B., Torres, B., Ferrández, A., Fernández, C., Miñambres, B., García, J.L., and Díaz, E., 2004, Aromatic metabolism versus carbon availability: The regulatory network that controls catabolism of less-preferred carbon sources in Escherichia coli. FEMS Microbiol. Rev., 28:503-518.
91. Pye, V.E., Tingey, A.P., Robson, R.L., and Moody, P.C., 2004, The structure and mechanism of serine acetyltransferase from E. coli. J. Biol. Chem., 279:40729-40736.
92. Rabus, R., Nordhaus, R., Ludwig, W., and Widdel, F., 1993, Complete oxidation of toluene under strictly anaerobic conditions by a new sulphate-reducing bacterium. Appl. Environ. Microbiol., 59:1444-1451.
93. Rabus, R., and Widdel, F., 1995, Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria. Arch. Microbiol., 163:96-103.
94. Ramos, J.L., González-Pérez, M.M., Caballero, A., and van Dillewijn, P., 2005, Bioremediation of polynitrated aromatic compounds: Plants and microbes put up a fight. Curr. Opin. Biotechnol., 516:275-281.
95. Ramos, J.L., and Timmis, K.N., 1987, Experimental evolution of catabolic pathways of bacteria. Microbiol. Sci., 4:228-237.
96. Rodríguez-Aparicio, L.B., Reglero, A., Martínez-Blanco, H., and Luengo, J.M., 1991, Fluorimetric determination of phenylacetyl-CoA ligase from Pseudomonas putida: A very sensitive assay for a new enzyme. Biochim. Biophys. Acta, 1073:431-433.
97. Rodríguez-Saiz, M., Barredo, J.L., Moreno, M.A., Fernández-Cañon, J.M., Peñalva, M.A., and Diez, B., Reduced function of a phenylacetate-oxidizing cytochrome p450 caused strong genetic improvement in early phylogeny of penicillin producing strains. J. Bacteriol., 183:5465-5471.
98. Rost, R., Haas, S., Hammer, E., Herrmann, H., and Burchhardt, G., 2002, Molecular analysis of aerobic phenylacetate degradation in Azoarcus evansii. Mol. Genet. Genomics, 267:656-663.
99. Saier, M.H. Jr., 2000, A functional-phylogenetic classification system for transmembrane solute transporters. Microbiol. Mol. Biol. Rev., 64:354-411.
100. Sariaslani, F.S., Harper, D.B., and Higgins, I.J., 1974, Microbial degradation of hydrocarbons. Catabolism of 1-phenylalkanes by Nocardia salmonicolor. Biochem. J., 140:31-45.
101. Sabelli, H., Fink, P., Fawcett, J., and Tom, C., 1996, Sustained antidepresant effect of PEA replacement. J. Neuropshychiatry Clin. Neurosci., 2:168-171.
102. Sandoval, A., Arias-Barrau, E., Bermejo, J., Cañedo, L., Naharro, G., Olivera, E.R., and Luengo, J.M., 2005, Production of 3-hydroxy-n-phenylalkanoic acids by a genetically engineered strain of Pseudomonas putida. Appl. Microbiol. Biotechnol., 67:97-105.
103. Schink, B., Brune, A., and Schnell, S., 1992, Anaerobic degradation of aromatic compounds, pp. 219-242. In G. Winkelmann (ed.), Microbial Degradation of Natural Products. VCH Weinheim, New York.
104. Schleissner, C., Olivera, E.R., Fernández-Valverde, M., and Luengo, J.M., 1994, Aerobic catabolism of phenylacetic acid in Pseudomonas putida U: biochemical characterization of a specific phenylacetic acid transport system and formal demonstration that phenylacetyl-coenzyme A is a catabolic intermediate. J. Bacteriol., 176:7667-7676.
105. Semple, K.T., and Cain, R.B., 1996, Biodegradation of phenols by the alga Ochromonas danica. Appl. Environ. Microbiol., 62:1256-1273.
106. Smith, M.R., 1990, The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation, 1:191-206.
107. Stanier, R.Y., and Orston, L.N., 1973, The β-ketoadipate pathway. Adv. Microb. Physiol., 9:89-151.
108. Steinebach, V., Benen, J.A., Bader, R., Postma, P.W., de Vries, S., and Duine, J.A., 1996, Cloning of the maoA gene that encodes aromatic amine oxidase of Escherichia coli W3350 and characterization of the overexpressed enzyme. Eur. J. Biochem., 237:584-591.
109. Sugino, H., Sasaki, M., Azakami, H., Yamashita, M., and Murooka, Y., 1992, A monoamine-regulated Klebsiella aerogenes operon containing the monoamine oxidase structural gene (maoA) and the maoC gene. J. Bacteriol., 174:2485-2492.
110. Sugumaran, M., and Vaidyanathan, C.S., 1979, Microsomal hydroxylation of phenylacetic acid by Aspergillus niger. FEMS Microbiol. Lett., 5:427-430.
111. Takami, H., Nakasone, K., Ogasawara, N., Hirama, C., Nakamura, Y., Masui, N., Fuji, F., Takaki, Y., Inoue, A., and Horikoshi, K., 1999, Sequencing of three lambda clones from the genome of alkaliphilic Bacillus sp. Strain C-125. Extremophiles, 3:29-34.
112. Timmis, K.N., and Pieper, H.D., 1999, Bacteria designed for bioremediation. Trends Biotechnol., 17:201-204.
113. Tokunaga, T., Nishimura, R., and Akagi, M., 1984, Muscarinic cholinergic receptors in human gastric mucosa. Jpn. J. Surg., 14:122-126.
114. Trias, J., and Nikaido, H., 1990, Protein D2 channel of the Pseudomonas aeruginosa outer membrane has a binding site for the basic amino acids and peptides. J. Biol. Chem., 265:15680-15684.
115. van den Tweel, W.J.J., Smits, J.P., and Bont, J.A.M., 1988, Catabolism of DL-a-phenylhydracrylic, phenylacetic and 3- And 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp. Arch. Microbiol., 149:207-213.
116. Velasco, A., Alonso, S., García, J.L., Perera, J., and Díaz, E., 1998, Genetic and functional analysis of the styrene catabolic cluster of Pseudomonas sp. strain Y2. J. Bacteriol., 180:1063-1071.
117. Vermeij, P., Vinke, E., Keltjens, J.T., and van der Drift, C., 1995, Purification and properties of coenzyme F390 hydrolase from Methanobacterium thermoautotrophicum (strain Marburg). Eur. J. Biochem., 234:592-597.
118. Villemur, R., 1995, Coenzyme A ligases involved in anaerobic biodegradation of aromatic compounds. Can. J. Microbiol., 41:855-861.
119. Vitovski, S., 1993, Phenylacetate-coenzyme A ligase is induced during growth on phenylacetic acid in different bacteria of several genera. FEMS Microbiol. Lett., 108:1-6.
120. Wackett, L.P., and Bruce, N.C., 2000, Environmental biotechnology. Towards sustainability. Curr. Opin. Biotechnol., 11:229-231.
121. Wacckett, L.P., and Ellis, L.B.M., 1999, Predicting biodegradation. Environ. Microbiol., 1:119-124.
122. Ward, P.G., and O'Connor, K.E., 2005, Induction and quantification of phenylacyl- CoA ligase enzyme activities in Pseudomonas putida CA-3 grown on aromatic carboxylic acids. FEMS Microbiol. Lett., 251:227-232.
123. Warhurst, A.M., and Fewson, C.A., 1994, Microbial metabolism and biotransformation of styrene. J. Appl. Bacteriol., 77:597-606.
124. Watanabe, K., and Hamamura, N., 2003, Molecular and physiological approaches to understanding the ecology of pollutant degradation. Curr. Opin. Biotechnol., 14:289-295.
125. Wheelis, M.L., and Stanier, R.Y., 1970, The genetic control of dissimilatory pathways in Pseudomonas putida. Genetics, 66:245-266.
126. Yang, H., Wolff, E., Kim, M., Diep, A., and Miller, J.H., 2004, Identification of mutator genes and mutational pathways in Escherichia coli using a multicopy cloning approach. Mol. Microbiol., 53:283-295.
127. Yen, K.-M., and Serdar, C.M., 1988, Genetic of naphtalene catabolism in pseudomonads. Crit. Rev. Microbiol., 15:247-268.
128. Zhang, C., and Bennett, G.N., 2005, Biodegradation of xenobiotics by anaerobic bacteria. Appl. Microbiol. Biotechnol., 67:600-618.
129. Zhou, J., Fries, M.R., Chee-Sanford, J.C., and Tiedje, J.M., 1995, Phylogenetic analysis of a new group of denitrifiers capable of anaerobic growth on toluene and description of Azoarcus tolulyticus sp. nov. Int. J. Syst. Bacteriol., 45:500-506.