Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions

Microbiological Reviews

Volumn 60, Issue 3, 1996, Pages 483-498

  Kaiser, Jean Pierre ^a,c   Feng, Yucheng ^a   Bollag, Jean Marc ^a,b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b 129 Land and Water Bldg ^*  (United States)

^c SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE;

AEROBIC METABOLISM; ANAEROBIC METABOLISM; BACTERIAL METABOLISM; BACTERIUM; NOCARDIA; NONHUMAN; REVIEW;

EID: 0029811543     PISSN: 01460749     EISSN: None     Source Type: Journal    
DOI: 10.1128/mmbr.60.3.483-498.1996     Document Type: Review

References (146)

1. Aislabie, J., A. K. Bej, H. Hurst, S. Rothenburger, and R. M. Atlas. 1990. Microhial degradation of quinoline and methylquinolines. Appl. Environ. Microbiol. 56:345-351.
2. Allison, M. J., W. R. Mayberry, C. S. McSweeney, and D. A. Stahl. 1992. Synergistes jonesii, gen. nov., sp. nov.: a rumen bacterium that degrades toxic pyridinediols. Syst. Appl. Microbiol. 15:522-529.
3. Amador, J. A., and B. F. Taylor. 1990. Coupled metabolic and photolytic pathway for degradation of pyridinedicarboxylic acids, especially dipicolinic acid. Appl. Environ. Microbiol. 56:1352-1356.
4. Arima, K., and Y. Kobayashi. 1962. Bacterial oxidation of dipicolinic acid. I. Isolation of microorganisms, their culture conditions, and end products. J. Bacteriol. 84:759-764.
5. Behrman, E. J., and R. Y. Stanier. 1957. The bacterial oxidation of nicotinic acid. J. Biol. Chem. 228:923-945.
6. Behrman, E. J., and R. Y. Stanier. 1957. Observations on the oxidation of halogenated nicotinic acids. J. Biol. Chem. 228:947-953.
7. Berry, D. F., A. J. Francis, and J.-M. Bollag. 1987. Microbial metabolism of homocyclic and heterocyclic aromatic compounds under anaerobic conditions. Microbiol. Rev. 51:43-59.
8. Bollag, J.-M., and J.-P. Kaiser. 1991. The transformation of heterocyclic aromatic compounds and their derivatives under anaerobic conditions. Crit. Rev. Environ. Control 21:297-329.
9. Bott, G., and F. Lingens. 1991. Microbial metabolism of quinoline and related compounds. IX. Degradation of 6-hydroxyquinoline and quinoline by Pseudomonas diminuta 31/1 Fa1 and Bacillus circulans 31/2 A1. Biol. Chem. Hoppe-Seyler 372:381-383.
10. Bott, G., M. Schmidt, T. O. Rommel, and F. Lingens. 1990. Microbial metabolism of quinoline and related compounds. V. Degradation of 1H-4-oxoquinoline by Pseudomonas putida 33/1. Biol. Chem. Hoppe-Seyler 371: 999-1003.
11. Boyd, D. R., R. Austin, S. McMordie, H. P. Porter, H. Dalton, R. O. Jenkins, and O. W. Howarth. 1987. Metabolism of bicyclic aza-arenes by Pseudomonas putida to yield vicinal cis-dihydrodiols and phenols. J. Chem. Soc. 22:1722-1724.
12. Brockman, F. J., B. A. Denovan, R. J. Hicks, and J. K. Fredrickson. 1989. Isolation and characterization of quinoline-degrading bacteria from subsurface sediment. Appl. Environ. Microbiol. 55:1029-1032.
13. 6. III. Metabolites of pyridoxamine. J. Biol. Chem. 235:1164-1169.
14. 6. VI. Pyridoxal dehydrogenase and 4-pyridoxolactonase. J. Biol. Chem. 244: 2585-2589.
15. Cain, R. B., C. Houghton, and K. A. Wright. 1974. Microbial metabolism of the pyridine ring. Metabolism of 2- and 3-hydroxypyridines by the maleamate pathway in Achromobacter sp. Biochcm. J. 140:293-300.
16. Dagley, S., and P. A. Johnson. 1963. Microbial oxidation of kynurenic, xanthurenic and picolinic acids. Biochim. Biophys. Acta 78:577-587.
17. Dominguez-Bello, M. G., and C. S. Stewart. 1990. Degradation of mimosine. 2,3-dihydroxypyridine and 3-hydroxy-4(1H)-pyridone by bacteria from the rumen of sheep in Venezuela. FEMS Microbiol. Ecol. 73:283-290.
18. Egorov, N. S., L. I. Vorob'eva, E. V. Dovgilevich, L. V. Modyanova, P. B. Terent'ev, O. K. Shibilkina, N. S. Kulikov, and O. V. Messinova. 1985. Hydroxylation of 2,6-dimethylpyridine and its analogs by microorganisms. Appl. Biochem. Microbiol. 21:277-281.
19. Ensign, J. C., and S. C. Rittenberg. 1963. A crystalline pigment produced from 2-hydroxypyridine by Arthrobacter crystallopoietes n. sp. Arch. Microbiol. 47:137-153.
20. Ensign, J. C., and S. C. Rittenberg. 1964. The pathway of nicotinic acid oxidation by a Bacillus species. J. Biol. Chem. 239:2285-2291.
21. Ensign, J. C., and S. C. Rittenberg. 1965. The formation of a blue pigment in the bacterial oxidation of isonicotinic acid. Arch. Microbiol. 51:384-392
22. Feng, Y., J.-P. Kaiser, R. D. Minard, and J.-M. Bollag. 1994. Microbial transformation of ethylpyridines. Biodegradation 5:121-128.
23. Fishbain, D., G. Ling, and D. J. Kushner. 1972. Isoniazid metabolism and binding by sensitive and resistant strains of Mycobacterium smegmatis. Can. J. Microbiol. 18:783-792.
24. Frankenburg, W. G., and A. A. Vaitekunas. 1955. Chemical studies on nicotine degradation by microorganisms derived from the surface of tobacco seeds. Arch. Biochem. Biophys. 58:509-512.
25. Gauthier, J. J., and S. C. Rittenberg. 1971. The metabolism of nicotinic acid. I. Purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N-9. J. Biol. Chem. 246:3737-3742.
26. Gauthier, J. J., and S. C. Rittenberg. 1971. The metabolism of nicotinic acid. II. 2,5-Dihydroxypyridine oxidation, product formation, and oxygen 18 incorporation. J. Biol. Chem. 246:3743-3748.
27. Gherna, R. L., S. H. Richardson, and S. C. Rittenberg. 1965. The bacterial oxidation of nicotine. VI. The metabolism of 2,6-dihydroxypseudooxynicotine. J. Biol. Chem. 240:3669-3674.
28. Gherna, R. L., and S. C. Rittenberg. 1962. Alternate pathways in nicotine degradation. Bacteriol. Proc. 1962, p. 27.
29. Grant, D. J. W., and T. R. Al-Najjar. 1976. Degradation of quinoline by a soil bacterium. Microbios 15:177-189.
30. Grbic-Galic, D. 1989. Microbial degradation of homocyclic and heterocyclic aromatic hydrocarbons under anaerobic conditions. Dev. Ind. Microbiol. 30:237-253.
31. Grbic-Galic, D. 1990. Anaerobic microbial transformation of monooxygenated aromatic and alicyclic compounds in soil, subsurface, and freshwater sediments, p. 117-189. In J.-M. Bollag and G. Stotzky (ed.). Soil biochemistry, vol. 6. Marcel Dekker, Inc., New York.
32. Gupta, R. C., and O. P. Shukla. 1975. Microbial metabolism of 2-hydroxy-pyridine. Indian J. Biochem. Biophys. 12:296-298.
33. Gupta. R. C., and O. P. Shukla. 1978. Metabolism of nicotinic acid by Sarcina sp. Indian J. Biochem. Biophys. 15:462-464.
34. Gupta, R. C., and O. P. Shukla. 1978. 2-Hydroxy-isonicotinic acid - an intermediate in metabolism of isonicotinic acid hydrazide and isonicotinic acid by Sarcina. Indian J. Biochem. Biophys. 15:492-493.
35. Gupta, R. C., and O. P. Shukla. 1978. Metabolism of isoniazid and related compounds by microorganisms: isolation, characterization and growth of isoniazid-degrading organisms. Indian J. Exp. Biol. 16:1047-1051.
36. Harary, I. 1956. Bacterial degradation of nicotinic acid. Nature (London) 177:328-329.
37. Harary, I. 1957. Bacterial fermentation of nicotinic acid. I. End products. J. Biol. Chem. 227:815-822.
38. Harary, I. 1957. Bacterial fermentation of nicotinic acid. II. Anaerobic reversible hydroxylation of nicotinic acid to 6-hydroxynicotinic acid. J. Biol. Chem. 227:823-831.
39. Hayaishi, O., H. Taniuchi, M. Tashiro, H. Yamada, and S. Kuno. 1959. Enzymatic formation of L-glutamic acid and acetic acid from kynurenic acid. J. Am. Chem. Soc. 81:3483-3484.
40. Hirschberg, R., and J. C. Ensign. 1971. Oxidation of nicotinic acid by a Bacillus species: purification and properties of nicotinic acid and 6-hydroxynicotinic acid hydroxylases. J. Bacteriol. 108:751-756.
41. Hirschberg, R., and J. C. Ensign. 1971. Oxidation of nicotinic acid by a Bacillus species: source of oxygen atoms for the hydroxylation of nicotinic acid and 6-hydroxynicotinic acid. J. Bacteriol. 108:757-759.
42. Hirschberg, R., and J. C. Ensign. 1972. Oxidation of nicotinic acid by a bacillus species: regulation of nicotinic acid and 6-hydroxynicotinic acid hydroxylases. J. Bacteriol. 112:392-397.
43. Hochstein, L. I., and B. P. Dalton. 1965. The hydroxylation of nicotine: the origin of the hydroxyl oxygen. Biochem. Biophys. Res. Commun. 21:644-648.
44. Hochstein, L. I., and B. P. Dalton. 1967. The purification and properties of nicotine oxidase. Biochim. Biophys. Acta 139:56-68.
45. Hochstein, L. I., and S. C. Rittenberg. 1959. The bacterial oxidation of nicotine. II. The isolation of the first oxidative product and its identification as (1)-6-hydroxynicotine. J. Biol. Chem. 234:156-160.
46. Hochstein, L. I., and S. C. Rittenberg. 1960. The bacterial oxidation of nicotine. III. The isolation and identification of 6-hydroxypseudooxynicotine. J. Biol. Chem. 235:795-799.
47. Holcenberg, J. S., and E. R. Stadtman. 1969. Nicotinic acid metabolism. III. Purification and properties of a nicotinic acid hydroxylase. J. Biol. Chem. 244:1194-1203.
48. 4g. Holcenberg, J. S., and L. Tsai. 1969. Nicotinic acid metabolism. IV. Ferredoxin-dependent reduction of 6-hydroxynicotinic acid to 6-oxo-1,4,5,6-tetrahydronicotinic acid. J. Biol. Chem. 244:1204-1211.
49. Holmes, P. E., and S. C. Rittenberg. 1972. The bacterial oxidation of nicotine. VII. Partial purification and properties of 2,6-dihydroxypyridine oxidase. J. Biol. Chem. 247:7622-7627.
50. Holmes, P. E., and S. C. Rittenberg. 1972. The bacterial oxidation of nicotine. VIII. Synthesis of 2,3,6-trihydroxypyridine and accumulation and partial characterization of the product of 2,6-dihydroxypyridine oxidation. J. Biol. Chem. 247:7628-7633.
51. Houghton, C., and R. B. Cain. 1972. Microbial metabolism of the pyridine ring. Biochem. J. 130:879-893.
52. Hughes, D. E. 1952. 6-Hydroxynicotinic acid as an intermediate in the oxidation of nicotinic acid by Pseudomonas fluorescens. Biochim. Biophys. Acta 9:226-227.
53. Hughes, D. E. 1955. 6-Hydroxynicotinic acid as an intermediate in the oxidation of nicotinic acid by Pseudomonas fluorescens. Biochem. J. 60:303-310.
54. Hund, H.-K., A. de Beyer, and F. Lingens. 1990. Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp. Biol. Chem. Hoppe-Seyler 371:1005-1008.
55. Hunt, A. L., D. E. Hughes, and J. M. Lowenstein. 1958. The hydroxylation of nicotinic acid by Pseudomonas fluorescens. Biochem. J. 69:170-173.
56. Hylin, J. W. 1959. The microbial degradation of nicotine. II. The mode of action of Achromobacter nicotinophagum. Arch. Biochem. Biophys. 83:528-537.
57. 6. II. Structure of "260 compound." J. Biol. Chem. 233:1555-1559.
58. Imhoff-Stuckle, D., and N. Pfennig. 1983. Isolation and characterization of a nicotinic acid-degrading sulfate-reducing bacterium, Desulfococcus niacini sp. nov. Arch. Microbiol. 136:194-198.
59. Jones, M. V., and D. E. Hughes. 1972. The oxidation of nicotinic acid by Pseudomonas ovalis chester. Biochem. J. 129:755-761.
60. Kaiser, J.-P., and J.-M. Bollag. 1991. Metabolism of pyridine and 3-hydroxypyridine under aerobic, denitrifying and sulfate-reducing conditions. Experientia 47:292-296.
61. Kaiser, J.-P., R. D. Minard, and J.-M. Bollag. 1993. Transformation of 3-and 4-picoline under sulfate-reducing conditions. Appl. Environ. Microbiol. 59:701-705.
62. Khanna, M., and O. P. Shukla. 1977. Microbial metabolism of 3-hydroxypyridine. Indian J. Biochem. Biophys. 14:301-302.
63. Knezovich, J. P., D. J. Bishop, T. J. Kulp, D. Grbic-Galic, and J. Dewitt. 1990. Anaerobic microbial degradation of acridine and the application of remote fiber spectroscopy to monitor the transformation process. Environ. Toxicol. Chem. 9:1235-1243.
64. Kobayashi, Y., and K. Arima. 1962. Bacterial oxidation of dipicolinic acid. II. Identification of α-ketoglutaric acid and 3-hydroxydipicolinic acid and some properties of cell-free extracts. J. Bacteriol. 84:765-771.
65. Kolenbrander, P. E., N. Lotong, and J. C. Ensign. 1976. Growth and pigment production by Arthrobacter pyridinolis n. sp. Arch. Microbiol. 110: 239-245.
66. Kolenbrander, P. E., and M. Weinberger. 1977. 2-Hydroxypyridine metabolism and pigment formation in three Arthrobacter species. J. Bacteriol. 132:51-59.
67. Korosteleva, L. A., A. N. Kost, L. I. Vorob'eva, L. V. Modyanova, P. B. Terent'ev, and N. S. Kulikov. 1981. Microbiological degradation of pyridine and 3-methylpyridine. Appl. Biochem. Microbiol. 17:276-283.
68. Kost, A. N., and L. V. Modyanova. 1978. Microbial transformation of pyridine derivatives. Chem. Heterocyclic Compounds 14:1049-1062.
69. Kost, A. N., L. I. Vorob'eva, P. B. Terent'ev, L. V. Modyanova, O. K. Shibilkina, and L. A. Korosteleva. 1977. Microbiological transformation of 2,6-dimethylpyridine. Appl. Biochem. Microbiol. 13:541-546.
70. Kuhn, E. P., and J. M. Suflita. 1989. Microbial degradation of nitrogen, oxygen and sulfur heterocyclic compounds under anaerobic conditions. Studies with aquifer samples. Environ. Toxicol. Chem. 8:1149-1158.
71. 12-dependent) and methylitaconate isomerase. J. Biol. Chem. 246:6436-6443.
72. Kung, H.-F., L. Tsai, and T. C. Stadtman. 1971. Nicotinic acid metabolism. VIII. Tracer studies on the intermediary roles of α-methyleneglutarate, methylitaconate, dimethylmaleate, and pyruvate. J. Biol. Chem. 246:6444-6451.
73. Lettau, H. 1980. Chemie der Heterocyclen. Deutscher Verlag für Grund-stoffindustrie, Leipzig, Germany.
74. Maeda, S., S. Uchida, and T. Kisaki. 1978. Microbial degradation of nicotine-N'-oxide degradation products. Agric. Biol. Chem. 42:1455-1460.
75. Modyanova, L. V., L. I. Vorob'eva, O. K. Shibilkina, E. V. Dovgilevich, and P. B. Terent'ev. 1990. Microbiological transformations of nitrogen-containing heterocyclic compounds. I. Hydroxylation of isomeric methyl- and dimeth-ylpyridines by certain microscopic fungi. Sov. Botechnol. 3:24-27.
76. Naik, M. N., R. B. Jackson, J. Stokes, and R. J. Swaby. 1972 Microbial degradation and phytotoxicity of picloram and other substituted pyridines. Soil Biol. Biochem. 4:313-323.
77. 6. VIII. Enzymatic breakdown of α-(N-acetylaminomethylene-)succinic acid. J. Biol. Chem. 244:2601-2605.
78. Ohsugi, M., Y. Inoue, K. Takami, and M. Namikawa. 1981. Microbial degradation of α-picolinic acid. 2-pyridinecarboxylic acid. Agric. Biol. Chem. 45:1879-1880.
79. Orpin, C. G., M. Knight, and W. C. Evans. 1971. The bacterial oxidation of N-methylisonicotinate. Biochem. J. 122:58P.
80. Orpin, C. G., M. Knight, and W. C. Evans. 1972. The bacterial oxidation of picolineamide, a photolytic product of diquat. Biochem. J. 127:819-831.
81. Orpin, C. G., M. Knight, and W. C. Evans. 1972. The bacterial oxidation of N-methylisonicotinate, a photolytic product of paraquat. Biochem. J. 127: 833-844.
82. Pastan, I., L. Tsai, and E. R. Stadtman. 1964. Nicotinic acid metabolism. I. Distribution of isotope in fermentation products of labeled nicotinic acid. J. Biol. Chem. 239:902-906.
83. Pereira, W. E., C. E. Rostad, T. J. Leiker, D. M. Updegraff, and J. L. Bennett. 1988. Microbial hydroxylation of quinoline in contaminated groundwater: evidence for incorporation of the oxygen atom of water. Appl. Environ. Microbiol. 54:827-829.
84. Pereira, W. E., C. E. Rostad, D. M. Updegraff, and J. L. Bennett. 1987. Fate and movement of azaarenes in an aquifer contaminated by wood-treatment chemicals. Environ. Toxicol. Chem. 6:163-176.
85. Pereira, W. E., C. E. Rostad, D. M. Updegraff, and J. L. Bennett. 1987. Anaerobic microbial transformations of azaarenes in ground water at hazardous waste sites, p. 111-123. In R. C. Averett and D. M. McKnight (ed.), Chemical quality of water and the hydrologic cycle. Lewis Publishers. Inc., Chelsea, Mich.
86. Racke, K. D., J. R. Coats, and K. R. Titus. 1988. Degradation of chlorpyrifos and its hydrolysis product 3,5,6-trichloro-2-pyridinol in soil. J. Environ. Sci. Health 23:527-539.
87. Racke, K. D., D. A. Laskowski, and M. R. Schultz. 1990. Resistance of chlorpyrifos to enhanced biodegradation in soil. J. Agric. Food Chem. 38:1430-1436.
88. Richardson, S. H., and S. C. Rittenberg. 1961. The bacterial oxidation of nicotine. IV. The isolation and identification of 2,6-dihydroxy-N-methyl-myosmine. J. Biol. Chem. 236:959-962.
89. Richardson, S. H., and S. C. Rittenberg. 1961. The bacterial oxidation of nicotine. V. Identification of 2,6-dihydroxypseudooxynicotine as the third oxidative product. J. Biol. Chem. 236:964-967.
90. 6. I. Isopyridoxal and 5-pyridoxic acid. J. Biol. Chem. 233:1548-1554.
91. Rogers, J. E., R. Riley, S. W. Li, M. L. O'Malley, and B. L. Thomas. 1985. Microbial transformation of alkylpyridines in groundwater. Water Air Soil Pollut. 24:443-454.
92. Rogers, P., A. Erben, and F. Lingens. 1990. Microbial metabolism of quinoline and related compounds. IV. Degradation of isoquinoline by Alcaligenes faecalis Pa and Pseudomonas diminuta 7. Biol. Chem. Hoppe-Seyler 371:511-513.
93. Ronen, Z., and J.-M. Bollag. 1991. Pyridine metabolism by a denitrifying bacterium. Can. J. Microbiol. 37:725-729.
94. Ronen, Z., and J.-M. Bollag. 1992. Rapid anaerobic mineralization of pyridine in a subsurface sediment inoculated with a pyridine-degrading Alcaligenes sp. Appl. Microbiol. Biotechnol. 37:264-269.
95. Ruger, A., G. Schwarz, and F. Lingens. 1993. Microbial metabolism of quinoline and related compounds. XIX. Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1. Biol. Chem. Hoppe-Seyler 374: 479-488.
96. Schach, S., G. Schward, S. Fetzner, and F. Lingens. 1993. Microbial metabolism of quinoline and related compounds. XVII. Degradation of 3-methylquinoline by Comamonas testosteroni 63. Biol. Chem. Hoppe-Seyler 374:175-181.
97. Schmidt, M., P. Rogers, and F. Lingens. 1991. Microbial metabolism of quinoline and related compounds. XI. Degradation of quinoline-4-carboxylic acid by Microbacterium sp. H2. Agrobacterium sp. 1B and Pimelobacter simplex 4B and 5B. Biol. Chem. Hoppe-Seyler 372:1015-1020.
98. Schwarz, G., R. Bauder, M. Speer, T. O. Rommel, and F. Lingens. 1989. Microbial metabolism of quinoline and related compounds. II. Degradation of quinoline by Pseudomonas fluorescens 3, Pseudomonas putida 86 and Rhodococcus spec. B1. Biol. Chem. Hoppe-Seyler 370:1183-1189.
99. Schwarz, G., E. Senghas, A. Erben, B. Schafer, F. Lingens, and H. Hoke. 1988. Microbial metabolism of quinoline and related compounds. I. Isolation and characterization of quinoline-degrading bacteria. Syst. Appl. Microbiol. 10:185-190.
100. Seyfried, B., and B. Schink. 1990. Fermentative degradation of dipicolinic acid (pyridine-2,6-dicarboxylic acid) by a defined coculture of strictly anaerobic bacteria. Biodegradation 1:1-7.
101. Shukla, O. P. 1973. Microbial decomposition of pyridinc. Indian J. Exp. Biol. 11:463-465.
102. Shukla, O. P. 1974. Microbial decomposition of α-picoline. Indian J. Biochem. Biophys. 11:192-200.
103. Shukla, O. P. 1975. Isolation, characterization and metabolic activities of a Bacillus sp. metabolizing α-picolinate. Indian J. Exp. Biol. 13:80-82.
104. Shukla, O. P. 1984. Microbial transformation of pyridine derivatives. J. Sci. Ind. Res. 43:98-116.
105. Shukla, O. P. 1984. 8-Hydroxycoumarin: an intermediate in the microbial transformation of quinoline. Curr. Sci. 53:1145-1147.
106. Shukla, O. P. 1986. Microbial transformation of quinoline by a Pseudomonas sp. Appl. Environ. Microbiol. 51:1332-1342.
107. Shukla, O. P., and S. M. Kaul. 1973. Microbial transformation of 2-picoline hy Bacillus sp. Indian J. Biochem. Biophys. 10:176-178.
108. Shukla, O. P., and S. M. Kaul. 1974. A constitutive pyridine degrading system in Corynebacterium sp. Indian J. Biochem. Biophys. 11:201-207.
109. Shukla, O. P., and S. M. Kaul. 1975. Succinate semialdehyde, an intermediate in the degradation of pyridine by Brevibacterium sp. Indian J. Biochem. Biophys. 12:326-330.
110. Shukla, O. P., and S. M. Kaul. 1986. Microbiological transformation of pyridine N-oxide and pyridine by Nocardia sp. Can. J. Microbiol. 32:330-341.
111. Shukla, O. P., S. M. Kaul, and M. Khanna. 1977. Microbial transformation of pyridine derivatives: α-picolinate metabolism by a gram-negative coccus. Indian J. Biochem. Biophys. 14:292-295.
112. Sims, G. K., and E. J. O'Loughlin. 1989. Degradation of pyridines in the environment. Crit. Rev. Environ. Control 19:309-340.
113. Sims, G. K., and E. J. O'Loughlin. 1992. Riboflavin production during growth of Micrococcus luteus on pyridine. Appl. Environ. Microbiol. 58: 3423-3425.
114. Sims, G. K., and L. E. Sommers. 1985. Degradation of pyridine derivatives in soil. J. Environ. Oual. 14:580-584.
115. Sims, G. K., and L. E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environ. Toxicol. Chem. 5:503-509.
116. Sims, G. K., L. E. Sommers, and A. Konopka. 1986. Degradation of pyridine by Micrococcus luteus isolated from soil. Appl. Environ. Microbiol. 51:963-968.
117. Singh, R. P. 1982. Studies on the utilization of dipicolinic acid as carbon and nitrogen source by a laboratory isolated strain of Bacillus brevis. Indian J. Exp. Biol. 20:223-226.
118. Singh, R. P., S. M. Kaul, and O. P. Shukla. 1980. Microbial decomposition of pyridine carboxylic acids and isoniazid by Bacilli. Indian J. Exp. Biol. 18:1514-1516.
119. Singh, H. P., and O. P. Shukla. 1977. Succinic semialdehyde: an intermediate in the degradation of isonicotinic acid by a Bacillus sp. Indian J. Biochem. Biophys. 18:88-89.
120. 6. VII. Purification, properties and mechanism of action of an oxygenase which cleaves the 3-hydroxypyridine ring. J. Biol. Chem. 244:2590-2600.
121. Stadtman, E. R., T. C. Stadtman, I. Pastan, and L. D. Smith. 1972. Clostridium barkeri sp. nov. J. Bacteriol. 110:758-760.
122. 6. V. The enzymatic formation of pyridoxal and isopyridoxal from pyridoxine. J. Biol. Chem. 244:2577-2584.
123. Taniuchi, H., and O. Hayaishi. 1963. Studies on the metabolism of kynurenic acid. III. Enzymatic formation of 7,8-dihydroxykynurenic acid from kynurenic acid. J. Biol. Chem. 238:283-293.
124. Taniuchi, H., M. Tashiro, K. Horibata, S. Kuno, O. Hayaishi, T. Sakan, S. Senoh, and T. Tokuyama. 1960. The enzymic formation of 7,8-dihydroxykynurenic acid from kynurenic acid. Biochim. Biophys. Acta 43:356-357.
125. Tate, R. L., and J. C. Ensign. 1974. A new species of Arthrobacter which degrades picolinic acid. Can. J. Microbiol. 20:691-694.
126. Tate, R. L., and J. C. Ensign. 1974. Picolinic acid hydroxylase of Arthrobacter picolinophilus. Can. J. Microbiol. 20:695-702.
127. Taylor, B. F., and J. A. Amador. 1988. Metabolism of pyridine compounds by phthalate-degrading bacteria. Appl. Environ. Microbiol. 54:2342-2344.
128. Taylor, B. F., and C. A. King. 1987. Phthalic acid and pyridine dicarboxylic acids as catabolic analogs. FEMS Microbiol. Lett. 44:401-405.
129. Tsai, L., I. Pastan, and E. R. Stadtman. 1966. Nicotinic acid metabolism. II. The isolation and characterization of intermediates in the fermentation of nicotinic acid. J. Biol. Chem. 241:1807-1813.
130. Tsai, L., and E. R. Stadtman. 1971. Anaerobic degradation of nicotinic acid Methods Enzymol. 18:233-249.
131. Unkefer, C. J., and R. E. London. 1984. In vivo studies of pyridine nucleotide metabolism in Escherichia coli and Saccharomyces cerevisiae by carbon-13 NMR spectroscopy. J. Biol. Chem. 259:2311-2320.
132. Vaughan, P. A., P. S. J. Cheetham, and C. J. Knowles. 1988. The utilization of pyridine carbonitriles and carboxamides by Nocardia rhodochrous LL100-21. J. Gen. Microbiol. 134:1099-1107.
133. Vorob'eva, L. I., I. A. Parshikov, M. Dorre, E. V. Dovgilevich, and L. V. Modyanova. 1990. Microbiological transformations of nitrogen-containing heterocyclic compounds. II. Hydroxylation of ethylpyridines by microscopic fungi. Sov. Biotechnol. 3:24-27.
134. Wada, E. 1956. Microbial degradation of nornicotine. Arch. Biochem. Biophys. 64:244-246.
135. Wada, E. 1957. Microbial degradation of the tobacco alkaloids, and some related compounds. Arch. Biochem. Biophys. 72:145-162.
136. Wada, E., and K. Yamasaki. 1954. Degradation of nicotine by soil bacteria. J. Am. Chem. Soc. 76:155-157.
137. Wallnöfer, P. R., and G. Engelhardt. 1984. Aromatic and heterocyclic structures, p. 277-327. In H.-J. Rehm and G. Reed (ed.), Biotechnology, vol. 6A. Verlag Chemie, Weinheim, Germany.
138. Wang, Y.-T., M. T. Suidan, and J. T. Pfeffer. 1984. Anaerobic biodegradation of indole to methane. Appl. Environ. Microbiol. 48:1058-1060.
139. Wang, Y.-T., M. T. Suidan, and J. T. Pfeffer. 1984. Anaerobic activated carbon filter for the degradation of polycyclic N-aromatic compounds. J. Water Pollut. Control Fed. 56:1247-1253.
140. Watson, G. K., and R. B. Cain. 1975. Microbial metabolism of the pyridine ring. Biochem. J. 146:157-172.
141. Watson, G. K., C. Houghton, and R. B. Cain. 1974. Microbial metabolism of the pyridine ring. The hydroxylation of 4-hydroxypyridine to pyridine-3,4-diol (3,4-dihydroxypyridine) by 4-hydroxypyridine-3-hydroxylase. Biochem. J. 140:265-276.
142. Watson, G. K., C. Houghton, and R. B. Cain. 1974. Microbial metabolism of the pyridine ring. The metabolism of pyridine-3,4-diol (3,4-dihydroxypyridine) by Agrobacterium sp. Biochem. J. 140:277-292.
143. Wright, K. A., and R. B. Cain. 1969. Microbial formation of methylamine from 4-carboxy-1-methyl-pyridinium chloride, a photolytic product of paraquat. Soil Biol. Biochem. 1:5-14.
144. Wright, K. A., and R. B. Cain. 1970. Microbial degradation of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat. Biochem. J. 118:52.
145. Wright, K. A., and R. B. Cain. 1972. Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat. Biochem. J. 128:543-559.
146. Wright, K. A., and R. B. Cain. 1972. Microbial metabolism of pyridinium compounds. Radioisotope studies of the metabolic fate of 4-carboxy-1-methyl-pyridinium chloride. Biochem. J. 128:561-568.