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. 1995 Jun;61(6):2159–2165. doi: 10.1128/aem.61.6.2159-2165.1995

Formation of Dimethylmuconolactones from Dimethylphenols by Alcaligenes eutrophus JMP 134

D H Pieper, K Stadler-Fritzsche, H Knackmuss, K N Timmis
PMCID: PMC1388459  PMID: 16535041

Abstract

2,3-, 2,4-, 2,5-, 3,4-, and 3,5-dimethylphenols were cometabolized by 2,4-dichlorophenoxyacetate-grown Alcaligenes eutrophus JMP 134 or the constitutive derivative JMP 134-1 via the ortho pathway into dimethylmuconolactones as dead-end products. Formation of two distinct lactones from 3,4-dimethylphenol is indicative of 2- as well as 6-hydroxylation. Induction of the meta-cleavage pathway by 2,3- and 3,4-dimethylphenols resulted in growth and no accumulation of products. In contrast, 3,5-dimethylphenol is not metabolized by the meta-cleavage pathway.

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Selected References

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  1. Baggi G., Barbieri P., Galli E., Tollari S. Isolation of a Pseudomonas stutzeri strain that degrades o-xylene. Appl Environ Microbiol. 1987 Sep;53(9):2129–2132. doi: 10.1128/aem.53.9.2129-2132.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bayly R. C., Dagley S., Gibson D. T. The metabolism of cresols by species of Pseudomonas. Biochem J. 1966 Nov;101(2):293–301. doi: 10.1042/bj1010293. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Bestetti G., Galli E. Characterization of a novel TOL-like plasmid from Pseudomonas putida involved in 1,2,4-trimethylbenzene degradation. J Bacteriol. 1987 Apr;169(4):1780–1783. doi: 10.1128/jb.169.4.1780-1783.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1006/abio.1976.9999. [DOI] [PubMed] [Google Scholar]
  5. Bruce N. C., Cain R. B., Pieper D. H., Engesser K. H. Purification and characterization of 4-methylmuconolactone methyl-isomerase, a novel enzyme of the modified 3-oxoadipate pathway in nocardioform actinomycetes. Biochem J. 1989 Aug 15;262(1):303–312. doi: 10.1042/bj2620303. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Buswell J. A. Metabolism of phenol and cresols by Bacillus stearothermophilus. J Bacteriol. 1975 Dec;124(3):1077–1083. doi: 10.1128/jb.124.3.1077-1083.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Catelani D., Fiecchi A., Galli E. Dextro-gamma-carboxymethyl-gamma-methyl-delta-alpha-butenolide. A 1,2-ring-fission product of 4-methylcatechol by Pseudomonas desmolyticum. Biochem J. 1971 Jan;121(1):89–92. doi: 10.1042/bj1210089. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Don R. H., Pemberton J. M. Properties of six pesticide degradation plasmids isolated from Alcaligenes paradoxus and Alcaligenes eutrophus. J Bacteriol. 1981 Feb;145(2):681–686. doi: 10.1128/jb.145.2.681-686.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Don R. H., Weightman A. J., Knackmuss H. J., Timmis K. N. Transposon mutagenesis and cloning analysis of the pathways for degradation of 2,4-dichlorophenoxyacetic acid and 3-chlorobenzoate in Alcaligenes eutrophus JMP134(pJP4). J Bacteriol. 1985 Jan;161(1):85–90. doi: 10.1128/jb.161.1.85-90.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Dorn E., Hellwig M., Reineke W., Knackmuss H. J. Isolation and characterization of a 3-chlorobenzoate degrading pseudomonad. Arch Microbiol. 1974;99(1):61–70. doi: 10.1007/BF00696222. [DOI] [PubMed] [Google Scholar]
  11. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of catechol. Biochem J. 1978 Jul 15;174(1):85–94. doi: 10.1042/bj1740085. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol 1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad. Biochem J. 1978 Jul 15;174(1):73–84. doi: 10.1042/bj1740073. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Harker A. R., Olsen R. H., Seidler R. J. Phenoxyacetic acid degradation by the 2,4-dichlorophenoxyacetic acid (TFD) pathway of plasmid pJP4: mapping and characterization of the TFD regulatory gene, tfdR. J Bacteriol. 1989 Jan;171(1):314–320. doi: 10.1128/jb.171.1.314-320.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Hartmann J., Reineke W., Knackmuss H. J. Metabolism of 3-chloro-, 4-chloro-, and 3,5-dichlorobenzoate by a pseudomonad. Appl Environ Microbiol. 1979 Mar;37(3):421–428. doi: 10.1128/aem.37.3.421-428.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Hopper D. J., Chapman P. J., Dagley S. The enzymic degradation of alkyl-substituted gentisates, maleates and malates. Biochem J. 1971 Mar;122(1):29–40. doi: 10.1042/bj1220029. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Hopper D. J., Chapman P. J. Gentisic acid and its 3- and 4-methyl-substituted homologoues as intermediates in the bacterial degradation of m-cresol, 3,5-xylenol and 2,5-xylenol. Biochem J. 1971 Mar;122(1):19–28. doi: 10.1042/bj1220019. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Kabisch M., Fortnagel P. Nucleotide sequence of metapyrocatechase I (catechol 2,3-oxygenase I) gene mpcI from Alcaligenes eutrophus JMP222. Nucleic Acids Res. 1990 Jun 11;18(11):3405–3406. doi: 10.1093/nar/18.11.3405. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Kabisch M., Fortnagel P. Nucleotide sequence of the metapyrocatechase II (catechol 2,3-oxygenase II) gene mpcII from Alcaligenes eutrophus JMP 222. Nucleic Acids Res. 1990 Sep 25;18(18):5543–5543. doi: 10.1093/nar/18.18.5543. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Knackmuss H. J., Hellwig M. Utilization and cooxidation of chlorinated phenols by Pseudomonas sp. B 13. Arch Microbiol. 1978 Apr 27;117(1):1–7. doi: 10.1007/BF00689343. [DOI] [PubMed] [Google Scholar]
  20. Kuhm A. E., Schlömann M., Knackmuss H. J., Pieper D. H. Purification and characterization of dichloromuconate cycloisomerase from Alcaligenes eutrophus JMP 134. Biochem J. 1990 Mar 15;266(3):877–883. [PMC free article] [PubMed] [Google Scholar]
  21. Kukor J. J., Olsen R. H., Siak J. S. Recruitment of a chromosomally encoded maleylacetate reductase for degradation of 2,4-dichlorophenoxyacetic acid by plasmid pJP4. J Bacteriol. 1989 Jun;171(6):3385–3390. doi: 10.1128/jb.171.6.3385-3390.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  22. Kunz D. A., Chapman P. J. Catabolism of pseudocumene and 3-ethyltoluene by Pseudomonas putida (arvilla) mt-2: evidence for new functions of the TOL (pWWO) plasmid. J Bacteriol. 1981 Apr;146(1):179–191. doi: 10.1128/jb.146.1.179-191.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Liu T., Chapman P. J. Purification and properties of a plasmid-encoded 2,4-dichlorophenol hydroxylase. FEBS Lett. 1984 Aug 6;173(2):314–318. doi: 10.1016/0014-5793(84)80797-8. [DOI] [PubMed] [Google Scholar]
  24. Nakazawa T., Yokota T. Benzoate metabolism in Pseudomonas putida(arvilla) mt-2: demonstration of two benzoate pathways. J Bacteriol. 1973 Jul;115(1):262–267. doi: 10.1128/jb.115.1.262-267.1973. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. 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]
  26. Peelen S., Rietjens I. M., van Berkel W. J., van Workum W. A., Vervoort J. 19F-NMR study on the pH-dependent regioselectivity and rate of the ortho-hydroxylation of 3-fluorophenol by phenol hydroxylase from Trichosporon cutaneum. Implications for the reaction mechanism. Eur J Biochem. 1993 Dec 1;218(2):345–353. doi: 10.1111/j.1432-1033.1993.tb18383.x. [DOI] [PubMed] [Google Scholar]
  27. Pettigrew C. A., Haigler B. E., Spain J. C. Simultaneous biodegradation of chlorobenzene and toluene by a Pseudomonas strain. Appl Environ Microbiol. 1991 Jan;57(1):157–162. doi: 10.1128/aem.57.1.157-162.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  28. Pieper D. H., Stadler-Fritzsche K., Engesser K. H., Knackmuss H. J. Metabolism of 2-chloro-4-methylphenoxyacetate by Alcaligenes eutrophus JMP 134. Arch Microbiol. 1993;160(3):169–178. doi: 10.1007/BF00249121. [DOI] [PubMed] [Google Scholar]
  29. Pieper D. H., Stadler-Fritzsche K., Knackmuss H. J., Engesser K. H., Bruce N. C., Cain R. B. Purification and characterization of 4-methylmuconolactone methylisomerase, a novel enzyme of the modified 3-oxoadipate pathway in the gram-negative bacterium Alcaligenes eutrophus JMP 134. Biochem J. 1990 Oct 15;271(2):529–534. doi: 10.1042/bj2710529. [DOI] [PMC free article] [PubMed] [Google Scholar]
  30. Powlowski J. B., Dagley S. beta-Ketoadipate pathway in Trichosporon cutaneum modified for methyl-substituted metabolites. J Bacteriol. 1985 Sep;163(3):1126–1135. doi: 10.1128/jb.163.3.1126-1135.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  31. Rojo F., Pieper D. H., Engesser K. H., Knackmuss H. J., Timmis K. N. Assemblage of ortho cleavage route for simultaneous degradation of chloro- and methylaromatics. Science. 1987 Dec 4;238(4832):1395–1398. doi: 10.1126/science.3479842. [DOI] [PubMed] [Google Scholar]
  32. SCHMIDT K., LIAAENJENSEN S., SCHLEGEL H. G. DIE CAROTINOIDE DER THIORHODACEAE. I. OKENON ALS HAUPTEAROTINOID VON CHROMATIUM OKENII PERTY. Arch Mikrobiol. 1963 Aug 1;46:117–126. [PubMed] [Google Scholar]
  33. Schlömann M., Fischer P., Schmidt E., Knackmuss H. J. Enzymatic formation, stability, and spontaneous reactions of 4-fluoromuconolactone, a metabolite of the bacterial degradation of 4-fluorobenzoate. J Bacteriol. 1990 Sep;172(9):5119–5129. doi: 10.1128/jb.172.9.5119-5129.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  34. Schlömann M., Schmidt E., Knackmuss H. J. Different types of dienelactone hydrolase in 4-fluorobenzoate-utilizing bacteria. J Bacteriol. 1990 Sep;172(9):5112–5118. doi: 10.1128/jb.172.9.5112-5118.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  35. Shingler V., Franklin F. C., Tsuda M., Holroyd D., Bagdasarian M. Molecular analysis of a plasmid-encoded phenol hydroxylase from Pseudomonas CF600. J Gen Microbiol. 1989 May;135(5):1083–1092. doi: 10.1099/00221287-135-5-1083. [DOI] [PubMed] [Google Scholar]
  36. Vollmer M. D., Stadler-Fritzsche K., Schlömann M. Conversion of 2-chloromaleylacetate in Alcaligenes eutrophus JMP134. Arch Microbiol. 1993;159(2):182–188. doi: 10.1007/BF00250280. [DOI] [PubMed] [Google Scholar]
  37. Williams P. A., Murray K. Metabolism of benzoate and the methylbenzoates by Pseudomonas putida (arvilla) mt-2: evidence for the existence of a TOL plasmid. J Bacteriol. 1974 Oct;120(1):416–423. doi: 10.1128/jb.120.1.416-423.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]

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