Bacterial scission of ether bonds

Microbiological Reviews

Volumn 60, Issue 1, 1996, Pages 216-232

  White, Graham F ^a   Russell, Nicholas J ^a,b   Tidswell, Edward C ^a,c  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c Grangestone Industrial Estate   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; ETHER;

BACTERIUM; BIOREMEDIATION; CHEMICAL MODEL; METABOLISM; POLLUTANT; REVIEW; BIODEGRADATION; MOLECULAR INTERACTION; NONHUMAN; OXIDATION; OXYGENATION;

BACTERIA; BIODEGRADATION, ENVIRONMENTAL; ENVIRONMENTAL POLLUTANTS; ETHERS; MODELS, CHEMICAL;

BACTERIA (MICROORGANISMS);

EID: 0029670192     PISSN: 01460749     EISSN: None     Source Type: Journal    
DOI: 10.1128/mmbr.60.1.216-232.1996     Document Type: Article

References (131)

1. Alexander, M. 1965. Biodegradation: problems of molecular recalcitrance and microbial fallibility. Adv. Appl. Microbiol. 7:35-80.
2. Ashton, F. M. 1982. Persistence and biodegradation of herbicides, p. 117-131. In F. Matsumura and C. R. Krishna Murti (ed.). Biodegradation of pesticides. Plenum Press, New York.
3. Bache, E., and N. Pfennig. 1981. Selective isolation of Acetobacterium woodii on methoxylated aromatic acids and determination of growth yields. Arch. Microbiol. 130:255-261.
4. Baggi, G., L. Beretta, E. Galli, C. Scolastico, and V. Treccani. 1978. Biodegradation of alkylphenol polyethoxylates, p. 127-136. In K. W. Chater and H. J. Somerville (ed.), The oil industry and microbial ecosystems. Heydon and Son Ltd.. London.
5. Berman, M. H., and A. C. Frazer. 1992. Importance of tetrahydrofolate and ATP in the anaerobic O-dcmethylation reaction for phenylmethylethers. Appl. Environ. Microbiol. 58:925-931.
6. Bernhardt, F.-H., E. Bill, A. X. Trautwein, and H. Twilfer. 1988 4-Methoxybenzoate monooxygenase from Pseudomonas putida: isolation, biochemical properties, substrate specificity, and reaction mechanism of the enzyme components. Methods Enzymol. 161:281-294.
7. Bernhardt, F.-H., H. Pachowsky, and H. Staudinger. 1975. A 4-methoxy O-demethylase from Pseudomonas putida. A new type of monooxgenase system. Eur. J. Biochem. 57:241-256.
8. Berth, P., G. Jakobi, E. Schmadel, M. J. Schwuger, and C. H. Krauch. 1975. The replacement of phosphates in detergents - possibilities and limits. Angew. Chem. Int. Ed. Engl. 14:94-102.
9. Butler, E. G., T. Tanaka, T. Ichida, H. Maruyama, A. P. Leber, and G. M. Williams. 1988. Induction of hepatic peroxisome proliferation in mice by lactofen, a diphenyl ether herbicide. Toxicol. Appl. Pharmacol. 93:72-80.
10. Cain, R. B. 1977. Surfactant biodegradation in waste waters, p. 283-327. In A. G. Callely, C. F. Forster, and D. A. Stafford (ed.), Treatment of industrial effluents. Hodder and Stoughton, London.
11. Cain, R. B. 1981. Microbial degradation of surfactants and "builder" components, p. 325-370. In T. Leisinger, R. Hutter, A. M. Cook, and J. Nüesch (ed.), Microbial degradation of xenobiotics and recalcitrant compounds. Academic Press Ltd., London.
12. Cain, R. B. 1992. Microbial degradation of synthetic polymers. Symp. Soc. Gen. Microbiol. 48:292-338.
13. Cartwright, N. J., K. S. Holdom, and D. A. Broadbent. 1971. Bacterial attack on phenolic ethers: dealkylation of higher ethers and further observations on O-demethylases. Microbios 3:113-130.
14. Cartwright, N. J., and A. R. W. Smith. 1967. Bacterial attack on phenolic ethers. An enzyme system demethylating vanillic acid. Biochem. J, 102:826-841.
15. Choquet, C. G., G. B. Patel, T. J. Beveridge, and G. D. Sprott. 1994. Stability of pressure extruded liposomes made from archaebacterial ether lipids. Appl. Microbiol. Biotechnol. 42:375-384.
16. Crawford, R. L., T. K. Kirk, J. M. Harkin, and E. McCoy. 1973. Bacterial cleavage of an arylglycerol-β-aryl ether bond. Appl. Microbiol. 25:322-324.
17. Crawford, R. L., E. McCoy, J. M. Harkin, T. K. Kirk, and J. R. Obst. 1973. Degradation of methoxylated benzoic acids by a Nocardia from a lignin-rich environment: significance to lignin degradation and effect of chloro substituents. Appl. Microbiol. 26:176-184.
18. Daniel, S. L., Z. Wu, and H. L. Drake. 1988. Growth of thermophilic acetogenic bacteria on methoxylated aromatic acids. FEMS Microbiol. Lett. 52:25-28.
19. 18O-methoxy substituent of 3-methoxybenzoic acid and other unlabelled methoxybenzoic acids by anaerobic bacteria. Appl. Environ. Microbiol. 54:1237-1242.
20. Doré, J., and M. P. Bryant. 1990. Metabolism of one-carbon compounds by the ruminai acetogen Syntrophococcus sucromutans. Appl. Environ. Microbiol. 56:984-989.
21. Dwyer, D. F., and J. M. Tiedje. 1986. Metabolism of polyethylene glycol by two anaerobic bacteria, Desulfovibrio desulfiincans and a Bacteroides sp. Appl. Environ. Microbiol. 52:852-856.
22. Eklund, R., A. A. Bergman, A. Granmo, and M. Berggren. 1990. Bioaccumulation of 4-nonylphenol in marine animals. A re-evaluation. Environ. Pollut. 64:107-120.
23. Eltis, L. D., U. Karlson, and K. N. Timmis. 1993. Purification and characterization of cytochrome P-450 from Rhodococcus rhodochrous. Eur. J. Biochem. 213:211-216.
24. Evans, W. C., B. S. W. Smith, H. N. Fernley, and J. I. Davies. 1971. Bacterial metabolism of 2,4-dichlorophenoxyacetate. Biochem. J. 122:543-551.
25. Fincher, E. L., and W. J. Payne. 1962. Bacterial utilization of ether glycols. Appl. Microbiol. 10:542-547.
26. 14C-labeled substituent of vanillate. Appl. Environ. Microbiol. 51:84-87.
27. Frings, J., and B. Schink. 1994. Fermentation of phenoxyethanol to phenol and acetate by a homoacetogenic bacterium. Arch. Microbiol. 162:199-204.
28. Frings, J., E. Schramm, and B. Schink. 1992. Enzymes involved in anaerobic polyethylene glycol degradation by Pelobacter venetianus and Bacteroides strain PG1. Appl. Environ. Microbiol. 58:2164-2167.
29. Gamar, Y., and J. K. Gaunt. 1971. Bacterial metabolism of 4-chloro-2-methylphenoxyacetate. Formation of glyoxylate by side-chain cleavage. Biochem. J. 122:527-531.
30. Gambacorta, A., A. Gliozzi, and M. De Rosa. 1995. Archaeal lipids and their biotechnological applications. World J. Microbiol. Biotechnol. 11:115-131.
31. Gaunt, J. K., and W. C. Evans. 1971. Metabolism of 4-chloro-2-methylphenoxyacetate by a soil pseudomonad. Preliminary evidence for the metabolic pathway. Biochem. J. 122:519-526.
32. Geiser, R. 1980. Sc.D. thesis. ETH, Zurich.
33. Gibson, S. A., and J. M. Suflita. 1994. Role of electron-donating cosubstrates in the anaerobic biotransformation of chlorophenoxyacetates to chlorophenols by a bacterial consortium enriched on phenoxyacetate. Biodegradation 5:51-57.
34. Giger, W., P. H. Brunner, and C. Schaffner. 1985. 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants. Science 225:623-625.
35. Gledhill, W. E. 1978. Microbial degradation of a new detergent builder, carboxymethyltartronate (CMT), in laboratory activated sludge systems. Water Res. 12:591-597.
36. Grant, M. A., and W. J, Payne. 1983. Alcaligenes faecalis var. denitrificans ability to degrade free ether glycols and other non-ionic detergents - growing anaerobically as a denitrifier. Biotechnol. Bioeng. 25:627-630.
37. Griffiths, E. T. 1987. Ph.D. thesis. University of Wales, Cardiff.
38. Griffiths, E. T., S. G. Hales, N. J. Russell, and G. F. White. 1987. Identification of hydrophobic metabolites formed during biodegradation of alkyl ethoxylate and alkyl ethoxy sulfate surfactants by Pseudomonas sp. DES1. Biotechnol. Appl. Biochem. 9:217-229.
39. Haines, J. R., and M. Alexander. 1975. Microbial degradation of polyethylene glycols. Appl. Microbiol. 29:621-625.
40. Hales, S. G., K. S. Dodgson, G. F. White, N. Jones, and G. K. Watson. 1982. Initial stages in the biodegradation of the surfactant sodium dodecyltriethoxy sulfate by a Pseudomonas sp. strain DES1. Appl. Environ. Microbiol. 44:790-800.
41. Hales, S. G., G. K. Watson, K. S. Dodgson, and G. F. White. 1986. A comparative study of the biodegradation of the surfactant sodium dodecyltriethoxy sulphate by four detergent-degrading bacteria. J. Gen. Microbiol. 132:953-961.
42. Hanify, J. A., P. Metcalf, C. L. Nobbs, and K. J. Worsley. 1981. Aerial spraying of 2,4,5-T and human birth malformation: an epidemiological investigation. Science 212:349-351.
43. Helling, C. S., J. M. Bollag, and J. E. Dawson. 1968. Cleavage of etheroxygen bonds in phenoxyacetic acid by an Arthrobacter species. J. Agric. Food Chem. 16:538-539.
44. Higgins, I. J., and R. G. Bums. 1975. Pesticides, p. 7-62. In I. J. Higgins and R. G. Burns (ed.), The chemistry and microbiology of pollution. Academic Press Ltd., London.
45. Hock, W. K., and H. D. Sisler. 1969. Metabolism of chloroneb by Rhizoctonia solani and other fungi. J. Agric. Food Chem. 17:123-128.
46. Hosoya, H., N. Miyazaki, Y. Sugisaki, E. Takanashi, M. Tsurufuji, M. Yamaski, and G. Tamura. 1978. Bacterial degradation of synthetic polymers and oligomers with special reference to the case of polyethylene glycol. Agric. Biol. Chem. 42:1545-1552.
47. Ichikawa, Y., Y. Kitamoto, and N. Hosoi. 1978. Degradation of polyethylene glycol dodecyl ethers by a Pseudomonad isolated from activated sludge. J. Ferment. Technol. 56:403-409.
48. Jenkins, L. D. L., and K. A. Cook. 1979. Microbial degradation of polyethylene glycols. J. Appl. Bacteriol. 47:75-85.
49. Jobling, S., and J. P. Sumpter. 1993. Detergent components in sewage effluent are weakly oestrogenic to fish: an in vitro study using rainbow trout (Oncorhyynchus mykiss) hepatocytes. Aquat. Toxicol. 27:361-372.
50. Karlson, U., D. F. Dwyer, S. W. Hooper, E. R. B. Moore, K. N. Timmis, and L. D. Eltis. 1993. Two independently regulated cytochromes P-450 in a Rhodococcus rhodochrous strain that degrades 2-ethoxyphenol and 4-methoxybenzoate. J. Bacteriol. 175:1467-1474.
51. Karsa, D. R., J. M. Goode, and J. P. Donnelly (ed.). 1991. Surfactants applications directory. Blackie, Glasgow, Scotland.
52. Kasmi, A. E., S, Rajasekharan, and S. W. Ragsdale. 1994. Anaerobic pathway for conversion of methyl group of aromatic methyl ethers to acetic acid by Clostridium thermoaceticum. Biochemistry 33:11217-11224.
53. Kawai, F. 1985. Existence of ether bond-cleaving enzyme in a polyethylene glycol-utilizing symbiotic mixed culture. FEMS Microbiol. Lett. 30:273-276.
54. Kawai, F. 1987. The biochemistry of degradation of polyethers. Crit. Rev. Biotechnol. 6:273-307.
55. Kawai, F., K. Hanada, Y. Tani, and K. Ogata. 1977. Bacterial degradation of water-insoluble polymer (polypropylene glycol). J. Ferment. Technol. 55:89-96.
56. Kawai, F., T. Kimura, M. Fukaya, Y. Tani, K. Ogata, T. Ueno, and H. Fukami. 1978. Bacterial oxidation of polyethylene glycol. Appl. Environ. Microbiol. 35:679-684.
57. Kawai, F., T. Kimura, Y. Tani, H. Yamada, and M. Kurachi. 1978. Purification and characterization of polyethylene glycol dehydrogenase involved in the bacterial metabolism of polyethylene glycol. Appl. Environ. Microbiol. 40:701-705.
58. Kawai, F., T. Okamoto, and T. Suzuki. 1985. Aerobic degradation of polypropylene glycol by Corynebacterium sp. J. Ferment. Technol. 63:239-244.
59. Kawai, F., and H. Yamanaka. 1986. Isolation of polytetramethylene glycol (PTMG)-assimilating microorganisms and conditions for PTMG degradation. Presented at the Annual Meeting of the Agricultural Chemistry Society, Kyoto, Japan, 1986.
60. Kidd, H., and D. R. James. 1991. The agrochemicals handbook. The Royal Society of Chemistry, Cambridge.
61. Kilbane, J. J., D. K. Chatterjee, J. S. Karns, S. T. Kellogg, and A. M. Chakrabarty. 1982. Biodegradation of 2,4,5-T by a pure culture of Pseudomonas cepacia. Appl. Environ. Microbiol. 44:72-78.
62. Kreft, J.-U., and B. Schink. 1993. Demethylation and degradation of phenylmethylethers by the sulfide-methylating homoacetogenic bacterium strain TMBS 4. Arch. Microbiol. 159:308-315.
63. Kreft, J.-U., and B. Schink. 1994. O-Demethylation by the homoacetogenic anaerobe Holophaga foetida studied by a new photometric methylation assay using electrochemically produced cob(I)alamin. Eur. J. Biochem. 226:945-951.
64. Lappin, H. M., M. P. Greaves, and J. H. Slater. 1985. Degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] by a synergistic microbial community. Appl. Environ. Microbiol. 49:429-433.
65. Lee, G. F., W. Rast, and R. A. Jones. 1978. Eutrophication of water bodies: insights for an age-old problem. Environ. Sci. Technol. 12:900-908.
66. Loos, M. A., R. N. Roberts, and M. Alexander. 1967. Phenols as intermediates in the decomposition of phenoxyacetates by an Arthrobacter species. Can. J. Microbiol. 13:679-690.
67. Loos, M. A., R. N. Roberts, and M. Alexander. 1967. Formation of 2,4-dichlorophenol and 2,4-dichloroanisole from 2,4-dichlorophenoxyacetate by Arthrobacter sp. Can. J. Microbiol. 13:691-699.
68. MacRae, I. C., M. Alexander, and A. D. Rovira. 1963. The decomposition of 4(2,4-dichlorophenoxy)butyric acid by a Flavobacter sp. J. Gen. Microbiol. 32:69-76.
69. Maki, H., N. Masuda, Y. Fujiwara, and M. Ike. 1994. Degradation of alkylphenol ethoxylates by Pseudomonas sp. strain TR01. Appl. Environ. Microbiol. 60:2265-2271.
70. Masai, E., Y. Katayama, S. Kubota, S. Kawai, M. Yamasaki, and N. Morohoshi. 1993. A bacterial enzyme degrading the model lignin compound β-etherase is a member of the glutathione-S-transferase superfamily. FEBS Lett. 323:135-140.
71. Masai, E., Y. Katayama, S. Nishikawa, M. Yamasaki, N. Morohoshi, and T. Haraguchi. 1989. Detection and localization of a new enzyme catalysing the β-aryl ether cleavage in the soil bacterium Pseudomonas paucimobilis SYK-6. FEBS Lett. 249:348-352.
72. McLeese, D. W. 1981. Lethality and accumulation of alkylphenols in aquatic fauna. Chemosphere 10:723-730.
73. Morgan, J. M., M. D. Morgan, and J. H. Wiersma (ed.). 1980. Water pollution, p. 181-212. In Introduction to environmental science. W. H. Freeman & Co., San Francisco.
74. Mueller, G. C., and U. H. Kim. 1978. Displacement of estradiol from estrogen receptors by simple alkylphenols. Endocrinology 102:1429-1435.
75. Nichols, P. D., and P. D. Franzmann. 1992. Unsaturated diether phospholipids in the antarctic methanogen Methanococcoides-burtonii. FEMS Microbiol. Lett. 98:205-208.
76. Niimi, A. J. 1986. Biological half lives of chlorinated diphenyl ethers in rainbow trout (Salmo gairdneri). Aquat. Toxicol. 9:105-116.
77. Obradors, N., and J. Aguilar. 1991. Efficient biodegradation of high-molecular-weight polyethylene glycols by pure cultures of Pseudomonas stutzen. Appl. Environ. Microbiol. 57:2383-2388.
78. Odier, E., and I. Artaud. 1992. Degradation of lignin, p. 161-191. in G. Winkelmann (ed.), Microbial degradation of natural products. VCH Verlagsgesellschaft, Weinheim, Germany.
79. Ogata, K., F. Kawai, M. Fukaya, and Y. Tani. 1975. Isolation of polyethylene glycols-assimilable bacteria. J. Ferment. Technol. 53:757-761.
80. Ohe, T., T. Mashino, and M. Hirobe. 1994. Novel metabolic pathway of arylethers by cytochrome P-450: cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom of the active species in cytochrome P-450 models and cytochrome P-450. Arch. Biochem. Biophys. 310:402-409.
81. Ono, H., and J. Nakanisi. 1987. Herbicide, CNP contamination in the lake Kasumigaura basin. Water Res. 21:669-675.
82. Paltauf, F. 1994. Ether lipids in biomembranes. Chem. Phys. Lipids 74:101-139.
83. Patoczka, J., and G. W. Pulliam. 1990. Biodegradation and secondary effluent toxicity of ethoxylated surfactants. Water Res. 24:965-972.
84. Payne, W. J., and R. L. Todd. 1966. Flavin-linked dehydrogenation of ether glycols by cell-free extracts of a soil bacterium. J. Bacteriol. 91:1533-1536.
85. Pearce, B. A., and M. T. Heydeman. 1980. Metabolism of di(ethylene glycol) [2-(2′-hydroxyethoxy)ethanol] and other short poly(ethylene glycol)s by gram-negative bacteria. J. Gen. Microbiol. 118:21-27.
86. Perry, R., P. W. W. Kirk, T. Stephenson, and J. N. Lester. 1984. Environmental aspects on the use of NTA as a detergent builder. Water Res. 18:255-276.
87. Peterson, D., and J. Llaneza. 1974. Identification of a carbon-oxygen lyase activity cleaving the ether linkage in carboxymethyloxysuccinic acid. Arch. Biochem. Biophys. 162:135-146.
88. Pfeifer, F., S. Schacht, J. Klein, and H. G, Trüper. 1989. Degradation of diphenylether by Pseudomonas cepacia. Arch. Microbiol. 152:515-519.
89. Ribbons, D. W. 1970. Stoichiometry of O-demethylase activity in Pseudomonas aeruginosa. FEBS Lett. 8:101-104.
90. Ribbons, D. W. 1971. Requirement of two protein fractions for O-demethylase activity in Pseudomonas testosteronii. FEBS Lett. 12:161-165.
91. Salanitro, J. P., L. A. Diaz, M. P. Williams, and H. L. Wisniewski. 1994. Isolation of a bacterial culture that degrades methyl t-butyl ether. Appl. Environ. Microbiol. 60:2593-2596.
92. Sariaslani, F. S. 1991. Microbial cytochromes P-450 and xenobiotic metabolism. Adv. Appl. Microbiol. 36:133-178.
93. Sariaslani, F. S., and D. A. Kunz. 1986. Induction of cytochrome P-450 in Streptomyces griseus by soybean flour. Biochem. Biophys. Res. Comm. 141: 405-410.
94. Schink, B., P. H. Janssen, and J. Frings. 1992. Microbial degradation of natural and new synthetic polymers. FEMS Microbiol. Rev. 103:311-316.
95. Schink, B., and M. Stieb. 1983. Fermentative degradation of polyethylene glycol by a strictly anaerobic, gram-negative, non-sporeforming bacterium, Pelobacter venetianus sp. nov. Appl. Environ. Microbiol. 45:1905-1913.
96. Schmid, A., R. Benz, and B. Schink. 1991. Identification of two porins in Pelobacter venetianus fermenting high-molecular-mass polyethylene glycols. J. Bacteriol. 173:4909-4913.
97. Schmidt, S., R.-M. Wittich, P. Fortnagel, D. Erdmann, and W. Francke. 1992. Metabolism of 3-methyldiphenyl ether by Sphingomonas sp. SS31. FEMS Microbiol. Lett. 96:253-258.
98. Schöberl, P. 1982. Biodegradation of cocoa fatty alcohol ethoxylate by Acinetobacter lwoffii strain ML. Tenside 19:329-339.
99. Schomburg, D., and M. Salzmann (ed.). 1991. Enzyme handbook. Springer-Verlag KG, Berlin.
100. Schramm, E., and B. Schink. 1991. Ether-cleaving enzyme and diol dehydratase involved in anaerobic polyethylene glycol degradation by a new Acetobacterium sp. Biodegradation 2:71-79.
101. Shaw, A. H. 1993. Surfactants update. Soap Cosmet. Chem. Spec. 69:24-32.
102. Sims, G. K., M. Radosevich, X. T. He, and S. J. Traina. 1990. The effects of sorption on the bioavailability of pesticides, p. 119-137. In W. B. Betts (ed.), Biodegradation: natural and synthetic materials. Springer-Verlag, London.
103. Soto, A. M., H. Justicia, J. W. Wray, and C. Sonnenschein. 1991. p-Nonyiphenol: an estrogenic xenobiotic released from modified polystyrene. Environ. Health Perspect. 92:167-173.
104. Spier, J. L. 1964. The Si-C bond and silicones. Chemistry 37:6-11.
105. Srinivasan, V. R., and J. W. Cary. 1987. Biodegradation of lignin by bacteria and molecular cloning of a gene for arylether cleavage, p. 267-274. In J. F. Kennedy (ed.). Wood and cellulosics. Ellis Horwood, Chichester, England.
106. 14C-labelled model surfactants. Water Res. 21:661-667.
107. Stirling, D. I., and H. Dalton. 1980. Oxidation of dimethyl ether, methyl formate and bromomethane by Methylococcus capsulatus (Bath). J. Gen. Microbiol. 116:277-283.
108. Strass, A., and B. Schink. 1986. Fermentation of polyethylene glycol via acetaldehyde in Pelobacter venetianus. Appl. Microbiol. Biotechnol. 25:37-42.
109. Stupperich, E. 1993. Recent advances in elucidation of biological corrinoid functions. FEMS Microbiol. Rev. 12:349-366.
110. Stupperich, E., and R. Konle. 1993. Corrinoid-dependent methyl transfer reactions are involved in methanol and 3,4-dimethoxybenzoate metabolism by Sporomusa ovata. Appl. Environ. Microbiol. 59:3110-3116.
111. Sutherland, J. B. 1986. Demethylation of veratrole by a cytochrome P-450 in Streptomyces setonii. Appl. Environ. Microbiol. 52:98-100.
112. Swisher, R. D. 1968. Exposure levels and oral toxicity of surfactants. Arch. Environ. Health 17:232-236.
113. Swisher, R. D. 1987. Background and perspective, p. 1-6. In M. J. Schick and F. M. Fowkes (ed.). Surfactant biodegradation. Marcel Dekker, Inc., New York.
114. Tanaka, K., and N. Pfennig. 1988. Fermentation of 2-methoxyethanol by Acetobacterium malicum sp. nov. and Pelobacter venetianus. Arch. Microbiol. 149:181-187.
115. Thélu, J., L. Medina, and J. Pelmont. 1980. Oxidation of polyoxyethylene oligomers by an inducible enzyme from Pseudomonas P 400. FEMS Microbiol. Lett. 8:187-190.
116. Tidswell, E. C., N. J. Russell, and G. F. White. Ether bond scission in the biodegradation of alcohol ethoxylate nonionic surfactants by Pseudomonas sp. strain SC25A. Microbiology, in press.
117. Tiedje, J. M., and M. Alexander. 1969. Enzymatic cleavage of the ether bonds of 2,4-dichlorophenoxyacetate. J. Agric. Food Chem. 17:1080-1084.
118. Trower, M. K., F. S. Sariaslani, and D. P. O'Keefe. 1989. Purification and characterization of a soybean flour-induced cytochrome P-450 from Streptomyces griseus. J. Bacteriol. 171:1781-1787.
119. Turner, A. H., F. S. Abram, V. M. Brown, and H. A. Painter. 1985. The biodegradability of two primary alcohol ethoxylate nonionic surfactants under practical conditions, and the toxicity of the biodegradation products to rainbow trout. Water Res. 19:45-51.
120. Wagener, S., and B. Schink. 1988. Fermentative degradation of nonionic surfactants and polyethylene glycol by enrichment cultures and by pure cultures of homoacetogenic and propionatc-forming bacteria. Appl. Environ. Microbiol. 54:561-565.
121. Watson, G. K., and N. Jones. 1977. The biodegradation of polyethylene glycols by sewage bacteria. Water Res. 11:95-100.
122. Watson, G. K., and N. Jones. 1979. The microbial degradation of nonionc surfactants. Soc. Gen. Microbiol. Q. 6:78-79.
123. Webb, E. C. 1992. Enzyme nomenclature. Academic Press. Inc., San Diego, Calif.
124. White, G. F. 1993. Bacterial biodegradation of ethoxylated surfactants. Pestic. Sci. 37:159-166.
125. White, G. F., and N. J. Russell. 1988. Mechanisms of bacterial biodegradation of alkyl sulphate and alkylpolyethoxy sulphate surfactants, p. 325-332. In D. R. Houghton, R. N. Smith, and H. O. W. Eggins (ed.), Biodeterioration 7. Elsevier Applied Science, London.
126. White, R., S. Jobling, S. A. Hoare, J. P. Sumpter, and M. G. Parker. 1994. Environmentally persistent alkylphenolic compounds are oestrogenic. Endocrinology 135:175-182.
127. Wittich, R.-M., S. Schmidt, and P. Fortnagel. 1990. Bacterial degradation of 3- and 4-carboxybiphenyl ether by Pseudomonas sp. NSS2. FEMS Microbiol. Lett. 67:157-160.
128. Yamanaka, K. 1991. Polyethylene glycol dehydrogenating activity demonstrated by dye-linked alcohol dehydrogenase of Rhodopseudomonas acidophila M402. Agric. Biol. Chem. 55:837-844.
129. Young, I. G., G. B. Cox, and F. Gibson. 1967. 2,3-Dihydroxybenzoate as a bacterial growth factor and its route of biosynthesis. Biochim. Biophys. Acta 141:319-331.
130. Young, I. G., and F. Gibson. 1969. Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli. Biochim. Biophys. Acta 177:401-411.
131. Zeikus, J. G. 1981. Lignin metabolism and the carbon cycle. Polymer biosynthesis, biodegradation and environmental recalcitrance. Adv. Microb. Ecol. 5:211-243.