Microbial degradation of phenol and phenolic derivatives

Engineering in Life Sciences

Volumn 13, Issue 1, 2013, Pages 76-87

  Krastanov, Albert ^a   Alexieva, Zlatka ^b   Yemendzhiev, Husein ^c  

^a UNIVERSITY OF FOOD TECHNOLOGIES   (Bulgaria)

^b INSTITUTE OF MICROBIOLOGY   (Bulgaria)

^c ASSEN ZLATAROV UNIVERSITY   (Bulgaria)

Author keywords

Bioremediation; Degradation of phenol and phenolic derivatives; Mathematical modeling; Microbial biodegradation dynamics; Microbial species

Indexed keywords

ANTIFUNGAL AGENTS; BROAD APPLICATION; CANDIDA TROPICALIS; DEGRADATION POTENTIAL; ENVIRONMENTAL BIOTECHNOLOGY; ENVIRONMENTAL POLLUTANTS; ENZYME SYSTEMS; INDUSTRIAL EFFLUENT; MICROBIAL BIODEGRADATION; MICROBIAL DEGRADATION; MICROBIAL SPECIES; PHENOLIC COMPOUNDS; PHENOLIC DERIVATIVE; TOXIC COMPOUNDS; TRICHOSPORON;

BACTERIA; BIODEGRADATION; BIOREMEDIATION; BIOTECHNOLOGY; DYNAMICS; MATHEMATICAL MODELS; MICROBIOLOGY; SEWAGE;

PHENOLS;

AROMATIC COMPOUND; CATECHOL DIOXYGENASE; CIS, CIS MUCONATE CYCLASE; OXYGENASE; PHENOL; PHENOL DERIVATIVE; PHENOL HYDROXYLASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

BACTERIUM; BIODEGRADATION; BIOTECHNOLOGY; ENVIRONMENTAL FATE; MICROBIAL ACTIVITY; NUMERICAL MODEL; OPTIMIZATION; PHENOL; PHENOLIC COMPOUND; YEAST;

ACINETOBACTER; ALCALIGENES; ASPERGILLUS; BACILLUS; BURKHOLDERIA; CANDIDA; CANDIDA ALBICANS; CANDIDA TROPICALIS; COPRINUS; ENVIRONMENTAL IMPACT; FUSARIUM; GEOTRICHUM; MATHEMATICAL MODEL; MICROBIAL DEGRADATION; MICROBIAL METABOLISM; MOLECULAR DYNAMICS; NONHUMAN; PENICILLIUM; PHANEROCHAETE; PICHIA; PLEUROTUS; PSEUDOMONAS; REVIEW; RHODOCOCCUS; TRICHOSPORON; TRICHOSPORON CUTANEUM; YARROWIA;

BACTERIA (MICROORGANISMS); CANDIDA TROPICALIS; FUNGI; PSEUDOMONAS; TRICHOSPORON CUTANEUM;

EID: 84872396065     PISSN: 16180240     EISSN: 16182863     Source Type: Journal    
DOI: 10.1002/elsc.201100227     Document Type: Review

References (127)

1. Sikkema, J., De Bont, J., Poolman, B., Mechanisms of membane toxicity of hydrocarbons. Microbiol. Rev. 1995, 59, 201-222.
2. Aggelis, G., Ehaliotis, C., Nerud, F., Stoychev, I. et al., Evaluation of white-rot fungi for detoxification and decolorization of effluents from green olive debittering process. Appl. Microbiol. Biotechnol. 2002, 59, 353-360.
3. Field, J. A., Lettinga, G., Treatment and detoxification of aqueous spruce bark extracts by Aspergillus niger. Water Sci. Technol. 1991, 24, 127-137.
4. Mahadewswamy, M., Mall, I. D., Prasad, B., Mishra, I. M., Removal of phenol by adsorption of coal fly ash and activated carbon. Pollut. Res. 1997, 16, 107-175.
5. Agency for Toxic Substances and Disease Registry (ATSOR), 1989.
6. Fedorak, P. M., Hrudey, S. E., Anaerobic degradation of phenolic compounds with application to treatment of industrial waste waters, Wise, D. L. (Ed.), Biotreatment Systems, CRC, Boca Raton 1988, pp. 170-212.
7. Calabrese, E. J., Kenyon, E. M., Calabrese, E. J. (Ed.), Air Toxics and Risk Assessments, Lewis Publishers, Inc., Chelsea, Michigan 1991.
8. Drinking Water Directive 80/778/EEC, Commission of the European Communities, 1980.
9. Ministry Ordinance No. 15, Ministry of Health and Welfare, Tokyo, Japan, 2000.
10. U.S. EPA Current National Recommended Water Quality Criteria. (accessed Aug 23, 2007).
11. Ajay, K. J., Vinod, K. G., Shubhi, J., Suhas, M., Removal of chlorophenols using industrial wastes. Environ. Sci. Technol. 2004, 38, 1195-1200.
12. Busca, G., Berardinelli, S., Resini, C., Arrighi, L., Technologies for the removal of phenol from fluid streams: a short review of recent developments. J. Hazard. Mater. 2008, 160, 265-288.
13. Chan, W. C., Fu, T. P., Adsorption/ion-exchange behavior between a water-insoluble cationic starch and 2-chlorophenol in aqueous solutions. J. Appl. Polym. Sci. 1998, 67, 1085-1092.
14. Danis, T. G., Albanis, T. A., Petrakis, D. E., Pomonis, P. I., Removal of chlorinated phenols from aqueous solutions by adsorption on alumina pillared clays and mesoporous alumina aluminum phosphates. Water Res. 1998, 32, 295-302.
15. Gonchaouk, V. V., Kucheruk, D. D., Kochkoden, V. M., Badekha, V. P., Removal of organic substances from aqueous solutions by reagent enhanced reverse osmosis. Desalination 2002, 143, 45-51.
16. Jain, A. K., Gupta, V. K., Jain, S., Removal of chlorophenols using industrial wastes. Environ. Sci. Technol. 2004, 38, 1195-1200.
17. Mokrini, A., Ousse, D., Esplugas, S., Oxidation of aromatic compounds with UV radiation/ozone/hydrogen peroxide. Water Sci. Technol. 1997, 35, 95-102.
18. Reardon, K., Mosteller, D., Rogers, J., Biodegradation kinetics of benzene, toluene and phenol as single and mixed substrates for Pseudomonas putida. Biotechnol. Bioeng. 2000, 69, 385-400.
19. Klein, J. A., Lee, D. D., Biological treatment of aqueous wastes from usual conversion processes. Biotechnol. Bioeng. 1978, 8, 379-390.
20. Talley, J. W., Sleeper, P. M., Roadblock to the implementation of biotreatment strategies, Bajpai, R. K., Zappi, M. E. (Eds.), Annuals of New York Academic of Sciences, Wiley, New York 1997, pp.17-29.
21. Thavasi, R., Jayalakshmi, S., Bioremediation potential of hydrocarbonoclastic bacteria in Cuddalore harbour waters (India). Res. J. Chem. Environ. 2003, 7, 17-22.
22. Alexander, M., Lustigman, B. K., Effect of chemical structure on microbial degradation of substituted benzenes. J. Agric. Food. Chem. 1986, 14, 410-417.
23. Topalova, Y., Ribarova, I., Kozuharov, D., Dimkov, R. et al., Structural/functional changes in activated sludge in PCP-and ONP-biodegradation technologies. Biotechnol. Biotec. Eq. 2007, 21, 28-33.
24. Watanabe, K., Yamamoto, S., Hino, S., Harayama, S., Population dynamics of phenol degrading bacteria in activated sludge determined by gyrB-targeted quantitative PCR. Appl. Environ. Microbiol. 1998, 64, 1203-1209.
25. Kahru, A., Maloverjan, A., Sillak, H., Pollumaa, L., The toxicity and fate of phenolic pollutants in the contaminated soils associated with the oil-shaleindustry. Environ. Sci. Pollut. Res. 2002, 1, 27-33.
26. Schie, P. M., Young, L. Y., Biodegradation of phenol: mechanisms and applications. Biorem. J. 2000, 4, 1-18.
27. Hinteregger, C. R., Leinter, M., Loidl, A., Streichshier, F., Degradation of phenol and phenolic compounds by Pseudomonas EKII. Appl. Microbiol. Biotechnol. 1992, 37, 252-295.
28. Kwon, K. H., Yeom, S. H., Optimal microbial adaptation routes for the rapid degradation of high concentration of phenol. Bioproc. Biosys. Eng. 2009, 32, 435-442.
29. Seker, S., Beyenal, H., Salih, B., Tomas, A., Multi-substrate growth kinetics of Pseudomonas putida for phenol removal. Appl. Microbiol. Biotechnol. 1997, 47, 610-614.
30. Farrell, A., Quilty, B., The enhancement of 2-chlorophenol degradation by a mixed microbial community when augmented with Pseudomonas putida CP1. Water Res. 2002, 36, 2443-2450.
31. Kargi, F., Eker, S., Kinetics of 2, 4-dichlorophenol degradation by Pseudomonas putida CP1 in batch culture. Int. Biodeterior. Biodegrad. 2004, 55, 25-28.
32. Kumar, A., Kumar, S., Biodegradation kinetics of phenol and catechol using Pseudomonas putida MTCC 1194. Biochem. Eng. J. 2005, 22, 151-159.
33. Shourian, M., Noghabi, K. A., Zahiri, H. S., Bagheri, T. et al., Efficient phenol degradation by a newly characterized Pseudomonas sp. SA01 isolated from pharmaceutical wastewaters. Desalination 2009, 246, 577-594.
34. Buswell, J. A., Metabolism of phenol and cresols by Bacillus stearothermophilus. J. Bacteriol. 1975, 124, 1077-1083.
35. Topalova, Y., Dimkov, R., Merdzhanov, D., Two steps for speeding up of phenol detoxication. Biotechnol. Biotec. Eq. 1995, 9, 55-59.
36. Muller, D., Schlomann, M., Reineke, W., Maleylacetate reductases in chloroaromatic-degrading bacteria using the modified ortho pathway: comparison of catalytic properties. J. Bacteriol. 1996, 178, 298-300.
37. Margesin, R., Fonteyne, P. A., Redl, B., Low-temperature biodegradation of high amounts of phenol by Rhodococcus spp. and basidiomycetous yeasts. Res. Microbiol. 2005, 156, 68-75.
38. Arutchelvan, A., Kanakasabai, V., Nagarajan, S., Muralikrishnan, V., Isolation and identification of novel high strength phenoldegrading bacterial strains from phenol formaldehyde resin manufacturing industrial wastewater. J. Hazard. Mater. 2005, 27, 238-243.
39. Kulkarni, M., Chaudhari, A., Microbial remediation of nitro-aromatic compounds: an overview. J. Environ. Manage. 2007, 85, 496-512.
40. Heitkamp, M. A., Camel, V., Reuter, T. J., Adams, W. J., Biodegradation of p-nitrophenol in an aqueous waste stream by immobilized bacteria. Appl. Environ. Microbiol. 1990, 56, 2967-2973.
41. Spain, J. C., Gibson, D. T., Pathway for biodegradation of p-nitrophenolin Moraxella sp. Appl. Environ. Microbiol. 1991, 32, 812-819.
42. Hanne, L., Kirk, L., Appel, S., Narayan, A. et al., Degradation and induction specificity in actinomycetes that degrade p-nitrophenol. Appl. Environ. Microbiol. 1993, 59, 3505-3508.
43. Galindez-Mayer, J., Ramon-Gallegos, J., Ruiz-Ordaz, N., Juarez-Ramirez, C. et al., Phenol and 4-chlorophenol biodegradation by yeast Candida tropicalis in a fluidized bed reactor. Biochem. Eng. J. 2008, 38, 147-157.
44. Kurtz, A. M., Crow, S. A., Transformation of chlororesorcinol by the hydrocarbonoclastic yeasts Candida maltosa, Candida tropicalis and Trichosporon oivide. Curr. Microbiol. 1997, 35, 165-168.
45. Kirkwood, A. E., Nalewajko, C., Fulthorpe, R. R., The effects of cyanobacterial exudateson bacterial growth and biodegradation of organic contaminants. Microb. Ecol. 2006, 51, 4-12.
46. Abdel-El-Haleem, D., Acinetobacter: environmental and biotechnological applications. Afr. J. Biotechnol. 2003, 2, 71-74.
47. Hao, O. J., Kim, M. H., Seagren, E. A., Kim, H., Kinetics of phenol and chlorophenol utilization by Acinotobacter species. Chemosphere 2002, 46, 797-807.
48. Mazzoli, R., Pessione, E., Giuffrida, M. G., Fattori, P. et al., Degradation of aromatic compounds by Acinetobacter radioresistens S13: growth characteristics on single substrates and mixtures. Arch. Microbiol. 2007, 188, 55-68.
49. Zhang, H., Luo, H., Kamagata, Y., Characterization of the phenol hydroxylase from Burkholderia kururiensis KP23 involved in trichloroethylene degradation by gene cloning and disruption. Microb. Environ. 2003, 18, 167-173.
50. O'Sullivan, L., Weightman, A., Jones, H., Marchbank, A. et al., Identifying the genetic basis of ecologically and biotechnologically useful functions of the bacterium Burkholderia vietnamiensis. Environ. Microbiol. 2007, 9, 1017-1034.
51. Cerniglia, C. E., Crow, S. A., Metabolism of aromatic hydrocarbons by yeast. Arch. Microbiol. 1981, 129, 9-13.
52. Katayama-Hirayama, K., Tobita, S., Hirayama, K., Biodegradation of phenol and monochlorophenols by yeast Rhodotorula glutinis. Water Sci. Technol. 1994, 30, 59-66.
53. Sampaio, J. P., Utilization of low molecular weight ligninrelated aromatic compounds for the selective isolation of yeasts: Rhodotorula vanillica, a new basidiomycetous yeast species. Syst. Appl. Microbiol. 1994, 17, 613-619.
54. Atagana, H. I., Biodegradation of phenol, o-cresol, m-cresol and pcresolby indigenous soil fungi in soil contaminated with creosote. W. J. Microbiol. Biotechnol. 2004, 20, 851-858.
55. Rocha, L. L., DeAguiar Cordeiro, R., Cavalcante, R. M., DoNascimento, R. F. et al., Isolation and characterization of phenol-degrading yeasts from an oil refinery wastewater in Brazil. Mycopathologia 2007, 164, 183-188.
56. Krug, M., Ziegler, H., Straube, G., Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. I. physiology of growth and substrate utilization. J. Basic Microbiol. 1985, 25, 103-110.
57. Chang, S. Y., Li, C. T., Hiang, S. Y., Chang, M. C., Intraspecific protoplast fusion of Candida tropicalis for enhancing phenol degradation. Appl. Microbiol. Biotechnol. 1995, 43, 534-538.
58. Adav, S. S., Chen, M. Y., Lee, D. J., Ren, N. Q., Degradation of phenol by aerobic granules and isolated yeast Candida tropicalis. Biotechnol. Bioeng. 2007, 96, 844-852.
59. Jiang, Y., Wen, J. P., Li, H. M., Yang, S. L. et al., The biodegradation of phenol at high concentration by the yeast Candida tropicalis. Biotechnol. Bioeng. 2005, 24, 243-247.
60. Yan, J., Jianping, W., Jia, X., Caiyin, Q. et al., Mutation of Candida tropicalis by irradiation with an He-Ne laser to increase its ability to degrade phenol. Appl. Environ. Microbiol. 2007, 73, 226-231.
61. Fialova, A., Boschke, E., Bley, T., Rapid monitoring of the biodegradation of phenol-like compounds by the yeast Candida maltosa using BOD measurements. Int. Biodeterior. Biodegrad. 2004, 54, 69-76.
62. Tsai, S. C., Tsai, L. D., Li, Y. K., An isolated Candida albicans TL3 capable of degrading phenol at large concentration. Biosci. Biotechnol. Biochem. 2005, 69, 2358-2367.
63. Kaszycki, P., Czechowska, K., Petryszak, P., Miedzobrodzki, J. et al., Methylotrophic extremophilic yeast Trichosporon sp.: a soil-derived isolate with potential applications in environmental biotechnology. Acta Biochim. Pol. 2006, 53, 463-473.
64. Middelhoven, W. J., Scorzetti, G., Fell, J. W., Systematics of the anamorphic basidiomycetous yeast genus Trichosporon Behrend with the description of five novel species: Trichosporon vadense, T. smithiae, T. dehoogii, T. scarabaeorum and T. gamsii. Int. J. Syst. Evolut. Microbiol. 2004, 54, 975-986.
65. Santos, V. L., Linardi, V. R., Phenol degradation by yeast isolated from industrial effluents. J. Gen. Appl. Microbiol. 2001, 47, 213-221.
66. Prenafeta-Boldu, F. X., Summerbell, R., de Hoog, G. S., Fungi growing on aromatic hydrocarbons: biotechnology's unexpected encounter with biohazard? FEMS Microbiol. Rev. 2006, 30, 109-130.
67. Tosi, S., Kostadinova, N., Krumova, E., Pashova, S. et al., Antioxidant enzyme activity of filamentous fungi isolated from Livingston Island, Maritime Antarctica. Polar Biol. 2010, 33, 1227-1237.
68. Santos, V. L., Linardi, V. R., Biodegradation of phenol by filamentous fungi isolated from industrial effluents-identification and degradation potential. Process Biochem. 2003, 39, 1001-1006.
69. Abrashev, R. I., Pashova, S. B., Stefanova, L. N., Vassilev, S. V. et al., Heat-shock-induced oxidative stress and antioxidant response in Aspergillus niger 26. Can. J. Microbiol. 2008, 54, 977-983.
70. Krivobok, S., Benoit-Guyod, J. L., Seigle-Murandi, F., Steiman, R. et al., Diversity in phenol metabolizing capability of 809 strains of micromycetes. Microbiologica 1994, 17, 51-60.
71. Jacob, J. H., Alsohaili, S., Isolation of two fungal strains capable of phenol biodegradation. J. Biol. Sci. 2010, 10, 162-165.
72. Mendonca, E., Martins, A., Anselmo, A. M., Biodegradation of natural phenolic compounds as single and mixed substrates by Fusarium flocciferum. Electron. J. Biotechnol. 2004, 7, 30-37.
73. Cai, W., Li, J., Zhang, Z., The characteristics and mechanisms of phenol biodegradation by Fusarium sp. J. Hazard. Mater. 2007, 148, 38-42.
74. Stoilova, I., Krastanov, A., Stanchev, V., Daniel, D. et al., Biodegradation of high amounts of phenol, catechol, 2, 4-dichlorophenol and 2, 6-dimethoxyphenol by Aspergillus awamori cells. Enzyme Microb. Technol. 2006, 39, 1036-1041.
75. Stainer, R. Y., Ornston, L. N., The β-ketoadipate pathway. Adv. Microb. Physiol. 1973, 9, 89-151.
76. Agarry, S. E., Durojaiye, A. O., Solomon, B. O., Microbial degradation of phenols: a review. Int. J. Environ. Pollut. 2008, 32, 12-28.
77. Bayly, C., Wigmore, J., Metabolism of phenol and cresols by mutants of Pseudomonas putida. J. Bacteriol. 1973, 113, 1112-1120.
78. Dagley, S., Gibson, D. T., The bacterial degradation of catechol. Biochem. J. 1965, 95, 46-74.
79. Divari, S., Valetti, F., Caposio, P., Pessione, E. et al., The oxygenase component of pieno hydroxylase from Acinetobacter radioresistens S13. Eur. J. Biochem. 2003, 270, 2244-2253.
80. Kirchner, U., Westphal, A. H., Muller, R., Berkel, W. J. H., Phenol hydroxylase from Bacillus thermoglucosidasius A7, a two-protein component monooxygenase with a dual role for FAD. J. Biol. Chem. 2003, 278, 47545-47553.
81. Oonanant, W., Sucharitakul, J., Yuvaniyama, J., Chaiyen, P., Crystallization and preliminary x-ray crystallographic analysis of 2-methyl-3-hydroxypyridine-5-carboxylicacid (MHPC) oxygenase from Pseudomonas sp. MA-1. Acta Crystallogr. 2005, 61, 312-314.
82. Eppink, M. H., Cammaart, E., van Wassenaar, D., Middelhoven, W. J. et al., Purification and properties of hydroquinone hydroxylase, an FAD-dependent monooxygenase involved in the catabolism of 4-hydroxybenzoate in Candida parapsilosis CBS604. Eur. J. Biochem. 2000, 267, 6832-6840.
83. Neujahr, H. Y., Kjellen, K. G., Phenol hydroxylase from yeast. Reaction with phenol derivatives. J. Biol. Chem. 1978, 253, 8835-8841.
84. Basha, K., Rajendran, A., Thangavelu, V., Recent advances in the biodegradation of phenol: a review. Asian J. Exp. Biol. Sci. 2010, 1, 219-234.
85. Neujahr, H. Y., Lindslo, S., Varga, J. M., Oxidation of phenols by cells and cell-free enzymes from Candida tropicalis. Antonie Leeuwenhoek 1974, 4, 209-216.
86. Nurk, A., Kasak, L., Kivisaar, M., Sequence of the gene (pheA) encoding phenol monooxygenase from Pseudomonas sp. EST100: expression in Escherichia coli and Pseudomonas putida. Gene 1991, 102, 13-18.
87. Perkins, E. J., Gordon, M. P., Caserer, O., Lurquin, P. F., Organization and sequence of the 2, 4-dichlorophenol hydroxylase and dichlorocatechol oxidative operons of plasmid pJP4. J. Bacteriol. 1990, 172, 2351-2359.
88. Kalin, M., Neujahr, H. Y., Weissmahr, R. N., Sejlitz, T. et al., Phenol hydroxylase from Trichosporon cutaneum: gene cloning, sequence analysis, and functional expression in Escherichia coli. J. Bacteriol. 1992, 174, 7112-7120.
89. Cejkova, A., Masak, J., Jirku, V., Fialova, A. et al., The level of phenol hydroxylase in Candida maltosa - the key activity for efficient aromatic compound biodegradation, Proceeding of International Conference on Waste Management and the Environment, Boston, 2002, 99-106.
90. Enroth, C., Neujahr, H., Schneider, G., Lindqvist, Y., The crystal structure of phenol hydroxylase in complex with FAD and phenol provides evidence for a concerted conformational change in the enzyme and its cofactor during catalysis. Structure 1998, 6, 605-617.
91. Nair, C. I., Jayachandran, K., Shahsidhar, S., Biodegradation of phenol. Afr. J. Biotechnol. 2008, 7, 4951-4958.
92. Roling, W. F. M., Hydrocarbon-degradation by acidophilic microorganisms, Timmis, K. N. (Ed.), Handbook of Hydrocarbon and Lipid microbiology. Springer-Verlag, Berlin Heidelberg 2010, pp. 1923-1930.
93. Tuckwell, D., Denning, D. W., Bowyer, P., A public resource for metabolic pathway mapping of Aspergillus fumigatus Af293. Med. Mycol. 2011, 49(Supl.1), 114-119.
94. Vaillancourt, F. H., Bolin, J. T., Eltis, L. D., The ins and outs of ring-cleaving dioxygenases. Crit. Rev. Biochem. Mol. Biol. 2006, 41, 241-267.
95. Kita, A., Kita, S., Fujisawa, I., Inaka, K. et al., Anarchetypical extradiol-cleaving catecholic dioxygenase: the crystal structure of catechol 2, 3-dioxygenase (metapyrocatechase) from Pseudomonas putida mt-2. Struct. Fold. Design 1999, 7, 25-34.
96. Takeo, M., Nishimura, M., Shirai, M., Takahashi, H. et al., Purification and characterization of catechol 2, 3-dioxygenase from the aniline degradation pathway of Acinetobacter sp. YAA and its mutant enzyme, which resists substrate inhibition. Biosci. Biotechnol. Biochem. 2007, 71, 1668-1675.
97. van der Meer, J. R., de Vos, M. W., Haramaya, S. et al., Molecular mechanism of genetic adaptation to xenobiotic compounds. Microbiol. Rev. 1992, 56, 677-694.
98. Wagner, H., Schwarz, T., Kaufmann, M., Phenol degradation by an enterobacterium: a Klebsiella strain carries a TOL-like plasmid and a gene encoding a novel phenol hydroxylase. Can. J. Microbiol. 1999, 45, 162-171.
99. Grekova-Vasileva, M., Topalova, Y., Enzyme activities and shifts in microbial populations associated with activated sludge treatment of textile effluents. Biotechnol. Biotec. Eq. 2008, 23, 1136-1142.
100. Nakai, C., Horiike, K., Kuramitsu, S., Kagamiyama, H. et al., Three isozymes of catechol l, 2-dioxygenase (Pyrocatechase), αα, αβ and ββ from Pseudomonas arvilla C-l. J. Biol. Chem. 1990, 265, 660-665.
101. Takenaka, S., Okugawa, S., Kadowaki, M., Murakami, S. et al., The metabolic pathway of 4-minophenol in Burkholderia sp. Strain AK-5 differs from that of aniline and aniline with C-4 substituents. Appl. Environ. Microbiol. 2003, 69, 5410-5413.
102. Matsumura, E., Ooi, S., Murakami, S., Takenaka, S. et al., Constitutive synthesis, purification, and characterization of catechol 1, 2-dioxygenase from the aniline-assimilating bacterium Rhodococcus sp. AN-22. J. Biosci. Bioeng. 2004, 98, 71-76.
103. Kalogeris, E., Sanakis, Y., Mamma, D., Christakopoulos, P. et al., Properties of catechol 1, 2-dioxygenase from Pseudomonas putida immobilized in calcium alginate hydrogels. Enz. Microb. Technol. 2006, 39, 1113-1121.
104. Lillis, L., Clipson, N., Doyle, E., Quantification of catechol dioxygenase gene expression in soil during degradation of 2, 4-dichlorophenol. FEMS Microbiol. Ecol. 2010, 73, 363-369.
105. Wang, C. L., You, S. L., Wang, S. L., Purification and characterization of a novel catechol 1, 2-dioxygenase from Pseudomonas aeruginosa with benzoic acid as a carbon source. Proc. Biochem. 2006, 41, 1594-1601.
106. Tsai, S. C., Li, Y. K., Purification and characterization of a catechol 1, 2-dioxygenase from a phenol degrading Candida albicans TL3. Arch. Microbiol. 2006, 187, 199-206.
107. Varga, J., Neujahr, H., Purification and properties of catechol 1, 2 - oxygenase from Trichosporon cutaneum. Eur. J. Biochem. 1970, 12, 427-434.
108. Aldrich, T. L., Chakrabarty, A. M., Transcriptional regulation, nucleotide sequence, and localization of the promoter of the catBC Operon in Pseudomonas putida. J. Bacteriol. 1988, 170, 1297-1304.
109. Neidle, E., Hartnett, C., Ornston, L., Characterization of Acinetobacter calcoaceticus catM, a repressor gene homologous in sequence to transcriptional activator genes. J. Bacteriol. 1989, 171, 5410-5421.
110. Thatcher, R., Cain, B., Purification and physical properties of 3-carboxy-cis-cis-muconate cyclase from Aspergillus niger. Eur. J. Biochem. 1974, 48, 549-556.
111. Bilton, F., Cain, B. The metabolism of aromatic acids by microorganisms. A reassessment of the role of o-benzoquinone as a product of protocatechuate metabolism by fungi. Biochem. J. 1968, 108, 828-832.
112. Mazur, P., Pieken, W., Budihas, S., Williams, S. et al., Cis, cis-muconate lactonizing enzyme from Trichosporon cutaneum: evidence for a novel class of cycloisomerases in eucaryotes. Biochemistry 1994, 33, 1961-1970.
113. Sakai, A., Fedorov, A. A., Fedorov, E. V., Schnoes, A. M. et al., Evolution of enzymatic activities in the enolase superfamily: stereochemically distinct mechanisms in two families of cis, cis-muconate lactonizing enzymes. Biochemistry 2009, 24, 1445-1453.
114. Okpokwasili, G. C., Nweke, C. O., Microbial growth and substrate utilization kinetics. Afr. J. Biotechnol. 2006, 5, 305-317.
115. Kumaran, P., Paruchuri, Y. L., Kinetics of phenol biotransformation. Water Res. 1997, 31, 11-22.
116. Vijayagopal, V., Viruthagiri, T., Batch kinetic studies in phenol biodegradation and comparison. Indian J. Biotechnol. 2005, 4, 565-567.
117. Zlateva, P., Gerginova, M., Manasiev, J., Atanasov, B. et al., Kinetic parameters determination of the phenolic derivatives assimilation by Trichosporon cutaneum R57. Biotechnol. Biotec. Eq. 2005, 19, 93-97.
118. Singh, R., Kumar, S., Kumar, S., Kumar, A., Biodegradation kinetic studies for the removal of p-cresol from wastewater using Gliomastix indicus MTCC 3869. Biochem. Eng. J. 2008, 40, 293-303.
119. Criddle, C. S., The kinetics of cometabolism. Biotechnol. Bioeng. 1993, 41, 1048-1056.
120. Hinchee, R., Anderson, D., Metting, F., Sayles, G. (Eds.), Applied Biotechnology for Site Remediation, CRC Press, Boca Raton 1994.
121. Gu, Y., Korus, R., Effects of p-cresol and chlorophenols on pentachlorophenol biodegradation. Appl. Microbiol. Biotechnol. 1995, 43, 347-378.
122. Hutchinson, D., Robinson, C., Kinetics of the simultaneous batch degradation of p-cresol and phenol by Pseudomonas putida. Appl. Microbiol. Biotechnol. 1988, 29, 599-604.
123. Reardon, K., Mosteller, D., Rogers, J., DuTeau, N. et al., Biodegradation kinetics of aromatic hydrocarbon mixtures by pure and mixed bacterial cultures. Environ. Health Perspect. 2002, 110, 1005-1011.
124. Alexieva, Z., Gerginova, M., Manasiev, J., Zlateva, P. et al., Phenol and cresol mixture degradation by the yeast Trichosporon cutaneum. J. Ind. Microbiol. Biotechnol. 2008, 35, 1297-1301.
125. Saravanan, P., Pakshirajan, K., Saha, P., Kinetics of phenol and m-cresol biodegradation by an indigenous mixed microbial culture isolated from a sewage treatment plant. J. Environ. Sci. 2008a, 20, 1508-1513.
126. Littlejohns, J. V., Daugulis, A. J., Kinetics and interactions of BTEX compounds during degradation by a bacterial consortium. Process Biochem. 2008, 43, 1068-1076.
127. Dimitriou-Christidis, P., Autenrieth, R. L., Kinetics of biodegradation of binary and ternary mixtures of PAHs. Biotechnol. Bioeng. 2006, 97, 788-800.