Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1975 Jan;146(1):157–172. doi: 10.1042/bj1460157

Microbial metabolism of the pyridine ring. Metabolic pathways of pyridine biodegradation by soil bacteria.

G K Watson, R B Cain
PMCID: PMC1165285  PMID: 1147895

Abstract

1. Two bacteria, a Bacillus sp. and a Nocardia sp. (strain Z1) were isolated from soil by enrichment with 0.1 percent (v/v) pyridine and grew rapidly on this compound as sole C, N and energy source. The monohydroxypyridines, tetrahydropyridine, piperidine and some other analogues were not utilized for growth or oxidized by washed suspensions of either bacterium. 2. Cell-free extracts were unable to metabolize pyridine even after supplementation with a variety of cofactors or protecting agents. Treatment of cells with toluene led to rapid loss of the ability to oxidize pyridine. 3. In the presence of 10mM-semicarbazide at pH 6.0, Nocardia Z1 accumulated a semialdehyde idenditied as its 2,4-dinitrophenylhydrazone by chromatography, mixed melting point, mass spectrometry and isotope trapping from [2,6(-14)C]pyridine as glutarate semialdehyde. 4. Extracts of this bacterium prepared from cells grown with pyridine or exposed to the gratuitous inducer 2-picoline, contained high activities of a specific glutarate semialdehyde dehydrogenase. 5. Cells grown with pyridine or glutarate also contained a glutaric dialdehyde dehydrogenase, an acyl-CoA synthetase and elevated amounts of isocitrate lyase but no glutaryl-CoA dehydrogenase. 6. Bacillus 4 accumulated in the presence of 10mM-semicarbazide several acidic carbonyl compounds from pyridine among which was succinate semialdehyde. Extracts of this bacillus after growth of the cells with pyridine contained an inducible succinate semialdehyde dehydrogenase in amounts at least 50-fold over those found in succinate-grown cells. 7. Two mutants of this bacillus, selected for their inability to grow on pyridine were deficient in succinate semialdehyde dehydrogenase. 8. In the presence of 0.2mM-KCN, washed suspensions of Bacillus 4 accumulated formate and possibly formamide from pyridine. The use of [14C]pyridine showed that formate was derived from C-2 of the pyridine ring. 9. The organism had a specific formamide amidohydrolase cleaving formamide quantitatively to formate and NH3. 10. Formate was further oxidized by the particle fraction. There was no soluble formate dehydrogenase in extracts.

Full text

PDF
157

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Axcell B. C., Geary P. J. The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase). Biochem J. 1973 Dec;136(4):927–934. doi: 10.1042/bj1360927. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BEHRMAN E. J., STANIER R. Y. The bacterial oxidation of nicotinic acid. J Biol Chem. 1957 Oct;228(2):923–945. [PubMed] [Google Scholar]
  3. Besrat A., Polan C. E., Henderson L. M. Mammalian metabolism of glutaric acid. J Biol Chem. 1969 Mar 25;244(6):1461–1467. [PubMed] [Google Scholar]
  4. Chamberlain E. M., Dagley S. The metabolism of thymol by a Pseudomonas. Biochem J. 1968 Dec;110(4):755–763. doi: 10.1042/bj1100755. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Dutton P. L., Evans W. C. The metabolism of aromatic compounds by Rhodopseudomonas palustris. A new, reductive, method of aromatic ring metabolism. Biochem J. 1969 Jul;113(3):525–536. doi: 10.1042/bj1130525. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. ENSIGN J. C., RITTENBERG S. C. A CRYSTALLINE PIGMENT PRODUCED FROM 2-HYDROXYPYRIDINE BY ARTHROBACTER CRYSTALLOPOIETES N.SP. Arch Mikrobiol. 1963 Dec 10;47:137–153. doi: 10.1007/BF00422519. [DOI] [PubMed] [Google Scholar]
  7. Eady R. R., Smith B. E., Cook K. A., Postgate J. R. Nitrogenase of Klebsiella pneumoniae. Purification and properties of the component proteins. Biochem J. 1972 Jul;128(3):655–675. doi: 10.1042/bj1280655. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Frigerio N. A., Shaw M. J. A simple method for determination of glutaraldehyde. J Histochem Cytochem. 1969 Mar;17(3):176–181. doi: 10.1177/17.3.176. [DOI] [PubMed] [Google Scholar]
  9. Gauthier J. J., Rittenberg S. C. The metabolism of nicotinic acid. I. Purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N-9. J Biol Chem. 1971 Jun 10;246(11):3737–3742. [PubMed] [Google Scholar]
  10. Gibson D. T., Koch J. R., Kallio R. E. Oxidative degradation of aromatic hydrocarbons by microorganisms. I. Enzymatic formation of catechol from benzene. Biochemistry. 1968 Jul;7(7):2653–2662. doi: 10.1021/bi00847a031. [DOI] [PubMed] [Google Scholar]
  11. HUGHES D. E. A press for disrupting bacteria and other micro-organisms. Br J Exp Pathol. 1951 Apr;32(2):97–109. [PMC free article] [PubMed] [Google Scholar]
  12. Hoet P. P., Stanier R. Y. Existence and functions of two enzymes with beta-ketoadipate: succinyl-CoA transferase activity in Pseudomonas florescens. Eur J Biochem. 1970 Mar 1;13(1):71–76. doi: 10.1111/j.1432-1033.1970.tb00900.x. [DOI] [PubMed] [Google Scholar]
  13. Houghton C., Cain R. B. Microbial metabolism of the pyridine ring. Formation of pyridinediols (dihydroxypyridines) as intermediates in the degradation of pyridine compounds by micro-organisms. Biochem J. 1972 Dec;130(3):879–893. doi: 10.1042/bj1300879. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Johnson P. A., Quayle J. R. Microbial growth on C-1 compounds. 6. Oxidation of methanol, formaldehyde and formate by methanol-grown Pseudomonas AM-1. Biochem J. 1964 Nov;93(2):281–290. doi: 10.1042/bj0930281. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  16. Meagher R. B., McCorkle G. M., Ornston M. K., Ornston L. N. Inducible uptake system for -carboxy-cis, cis-muconate in a permeability mutant of Pseudomonas putida. J Bacteriol. 1972 Aug;111(2):465–473. doi: 10.1128/jb.111.2.465-473.1972. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. NISHIZUKA Y., KUNO S., HAYAISHI O. Enzymic formation of acetyl-CoA and carbon dioxide from glutaryl-CoA. Biochim Biophys Acta. 1960 Sep 23;43:357–360. doi: 10.1016/0006-3002(60)90456-x. [DOI] [PubMed] [Google Scholar]
  18. NUMA S., ISHIMURA Y., NAKAZAWA T., OKAZAKI T., HAYAISHI O. ENZYMIC STUDIES ON THE METABOLISM OF GLUTARATE IN PSEUDOMONAS. J Biol Chem. 1964 Nov;239:3915–3926. [PubMed] [Google Scholar]
  19. OLSON J. A. The purification and properties of yeast isocitric lyase. J Biol Chem. 1959 Jan;234(1):5–10. [PubMed] [Google Scholar]
  20. Ornston L. N., Stanier R. Y. The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. J Biol Chem. 1966 Aug 25;241(16):3776–3786. [PubMed] [Google Scholar]
  21. Orpin C. G., Knight M., Evans W. C. The bacterial oxidation of N-methylisonicotinate, a photolytic product of paraquat. Biochem J. 1972 May;127(5):833–844. doi: 10.1042/bj1270833. [DOI] [PMC free article] [PubMed] [Google Scholar]
  22. SHILO M., STANIER R. Y. The utilization of the tartaric acids by pseudomonads. J Gen Microbiol. 1957 Apr;16(2):482–490. doi: 10.1099/00221287-16-2-482. [DOI] [PubMed] [Google Scholar]
  23. Scott T. A. A method for the degradation of radioactive nicotinic acid. Biochem J. 1967 Jan;102(1):87–93. doi: 10.1042/bj1020087. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Stafford D. A., Callely A. G. Properties of a pyridine-degrading organism. J Gen Microbiol. 1970 Nov;63(3):xiv–xiv. [PubMed] [Google Scholar]
  25. Tsai L., Pastan I., Stadtman E. R. Nicotinic acid metabolism. II. The isolation and characterization of intermediates in the fermentation of nicotinic acid. J Biol Chem. 1966 Apr 25;241(8):1807–1813. [PubMed] [Google Scholar]
  26. Watson G. K., Houghton C., Cain R. B. Microbial metabolism of the pyridine ring. The metabolism of pyridine-3,4-diol (3,4-dihydroxypyridine) by Agrobacterium sp. Biochem J. 1974 May;140(2):277–292. doi: 10.1042/bj1400277. [DOI] [PMC free article] [PubMed] [Google Scholar]
  27. Wright K. A., Cain R. B. Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat. Biochem J. 1972 Jul;128(3):543–559. doi: 10.1042/bj1280543. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES