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PMID: 3542963 Published · ppublish English Journal Article

Roles of the divergent branches of the meta-cleavage pathway in the degradation of benzoate and substituted benzoates.

Journal of bacteriology ·Vol. 169 ·No. 2 ·1987-02-00 ·Pages 558-64

Harayama S, Mermod N, Rekik M, Lehrbach PR, Timmis KN

Abstract

The TOL plasmid-specified meta-cleavage pathway for the oxidative catabolism of benzoate and toluates branches at the ring cleavage products of catechols and reconverges later at 2-oxopent-4-enoate or its corresponding substituted derivatives. The hydrolytic branch of the pathway involves the direct formation of 2-oxopent-4-enoate or its derivatives, whereas the oxalocrotonate branch involves three enzymatic steps effected by a dehydrogenase, an isomerase, and a decarboxylase, which produce the same compounds. Evidence is presented which shows that benzoate and p-toluate can, under certain circumstances, be catabolized by the hydrolytic branch. However, in a fully functional pathway, only m-toluate is dissimilated via this branch, and benzoate and p-toluate are catabolized almost exclusively by the oxalocrotonate branch. The biochemical basis of this selectivity was found to reside in the high affinity of the dehydrogenase for ring fission products derived from benzoate and p-toluate and its inability to attack the ring fission product derived from m-toluate. Although isomerization of 4-oxalocrotonate occurs spontaneously in vitro, enzymatic isomerization was found to be essential for effective functioning of this branch of the pathway in vivo.

MeSH Terms
Benzoates/metabolism Benzoic Acid Escherichia coli/genetics,metabolism Kinetics Mutation Phenotype Plasmids Species Specificity Structure-Activity Relationship
Chemicals
Benzoates Benzoic Acid
Authors & Affiliations
5 authors, click to expand affiliations / ORCID
Harayama S
Mermod N
Rekik M
Lehrbach P R
Timmis K N
References (36)
36 references, click to expand
  1. The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. IV. Regulation.
    J Biol Chem. 1966 Aug 25;241(16):3800-10 PMID: 5916393
  2. Transposon mutagenesis analysis of meta-cleavage pathway operon genes of the TOL plasmid of Pseudomonas putida mt-2.
    J Bacteriol. 1984 Oct;160(1):251-5 PMID: 6090417
  3. Transcription of the TOL plasmid toluate catabolic pathway operon of Pseudomonas putida is determined by a pair of co-ordinately and positively regulated overlapping promoters.
    EMBO J. 1984 Nov;3(11):2461-6 PMID: 6096122
  4. Genetic analysis of a relaxed substrate specificity aromatic ring dioxygenase, toluate 1,2-dioxygenase, encoded by TOL plasmid pWW0 of Pseudomonas putida.
    Mol Gen Genet. 1986 Feb;202(2):226-34 PMID: 3010045
  5. A new metabolic pathway of catechol.
    J Biol Chem. 1962 Jan;237:PC268-PC270 PMID: 14480006
  6. THE BACTERIAL DEGRADATION OF CATECHOL.
    Biochem J. 1965 May;95:466-74 PMID: 14340096
  7. Metabolism of arylsulphonates by micro-organisms.
    Biochem J. 1968 Feb;106(4):859-77 PMID: 5637368
  8. Oxoenoic acids as metabolites in the bacterial degradation of catechols.
    Biochem J. 1969 Feb;111(3):303-7 PMID: 5767053
  9. Supercoiled circular DNA-protein complex in Escherichia coli: purification and induced conversion to an opern circular DNA form.
    Proc Natl Acad Sci U S A. 1969 Apr;62(4):1159-66 PMID: 4894690
  10. Phenol and benzoate metabolism by Pseudomonas putida: regulation of tangential pathways.
    J Bacteriol. 1969 Nov;100(2):869-77 PMID: 5354952
  11. The meta cleavage of catechol by Azotobacter species. 4-Oxalocrotonate pathway.
    Eur J Biochem. 1971 Jun 11;20(3):400-13 PMID: 4325686
  12. The coexistence of two pathways for the metabolism of 2-hydroxymuconic semialdehyde in a naphthalene-grown pseudomonad.
    Biochem Biophys Res Commun. 1971 May 7;43(3):463-9 PMID: 4327441
  13. Dissimilation of aromatic compounds by Alcaligenes eutrophus.
    J Bacteriol. 1971 Aug;107(2):468-75 PMID: 5113598
  14. The metabolism of benzoate and methylbenzoates via the meta-cleavage pathway by Pseudomonas arvilla mt-2.
    Eur J Biochem. 1972 Jul 24;28(3):301-10 PMID: 4342906
  15. The metabolic divergence in the meta cleavage of catechols by Pseudomonas putida NCIB 10015. Physiological significance and evolutionary implications.
    Eur J Biochem. 1972 Jul 24;28(3):347-56 PMID: 4342908
  16. Stereospecific enzymes in the degradation of aromatic compounds by pseudomonas putida.
    J Bacteriol. 1973 Feb;113(2):922-31 PMID: 4690969
  17. Metabolism of phenol and cresols by mutants of Pseudomonas putida.
    J Bacteriol. 1973 Mar;113(3):1112-20 PMID: 4347965
  18. Benzoate metabolism in Pseudomonas putida(arvilla) mt-2: demonstration of two benzoate pathways.
    J Bacteriol. 1973 Jul;115(1):262-7 PMID: 4717515
  19. 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):416-23 PMID: 4418209
  20. Pseudomonas putida mutants defective in the metabolism of the products of meta fission of catechol and its methyl analogues.
    J Bacteriol. 1974 Oct;120(1):31-7 PMID: 4418942
  21. Bacterial degradation of 4-hydroxyphenylacetic acid and homoprotocatechuic acid.
    J Bacteriol. 1974 Oct;120(1):159-67 PMID: 4420192
  22. Transmissible plasmid coding for the degradation of benzoate and m-toluate in Pseudomonas arvilla mt-2.
    Genet Res. 1974 Apr;23(2):227-32 PMID: 4424218
  23. Metabolism of toluene and xylenes by Pseudomonas (putida (arvilla) mt-2: evidence for a new function of the TOL plasmid.
    J Bacteriol. 1975 Oct;124(1):7-13 PMID: 1176436
  24. Purification and properties of 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase from two strains of Pseudomonas putida.
    J Bacteriol. 1978 Apr;134(1):30-7 PMID: 77272
  25. Construction and characterization of amplifiable multicopy DNA cloning vehicles derived from the P15A cryptic miniplasmid.
    J Bacteriol. 1978 Jun;134(3):1141-56 PMID: 149110
  26. Regulation of the degradative pathway enzymes coded for by the TOL plasmid (pWWO) from Pseudomonas putida mt-2.
    J Bacteriol. 1978 Jun;134(3):757-64 PMID: 659369
  27. Isolation of large bacterial plasmids and characterization of the P2 incompatibility group plasmids pMG1 and pMG5.
    J Bacteriol. 1978 Jul;135(1):227-38 PMID: 97269
  28. Mutants defective in isomerase and decarboxylase activities of the 4-hydroxyphenylacetic acid meta-cleavage pathway in Pseudomonas putida.
    J Bacteriol. 1980 May;142(2):480-5 PMID: 6769900
  29. Molecular cloning of gene xylS of the TOL plasmid: evidence for positive regulation of the xylDEGF operon by xylS.
    J Bacteriol. 1981 Nov;148(2):413-8 PMID: 6271729
  30. TOL plasmid pWW0 in constructed halobenzoate-degrading Pseudomonas strains: prevention of meta pathway.
    J Bacteriol. 1982 Apr;150(1):195-201 PMID: 7061393
  31. Molecular and functional analysis of the TOL plasmid pWWO from Pseudomonas putida and cloning of genes for the entire regulated aromatic ring meta cleavage pathway.
    Proc Natl Acad Sci U S A. 1981 Dec;78(12):7458-62 PMID: 6950388
  32. Plasmid gene organization: naphthalene/salicylate oxidation.
    Proc Natl Acad Sci U S A. 1982 Feb;79(3):874-8 PMID: 6278499
  33. Specific-purpose plasmid cloning vectors. II. Broad host range, high copy number, RSF1010-derived vectors, and a host-vector system for gene cloning in Pseudomonas.
    Gene. 1981 Dec;16(1-3):237-47 PMID: 6282695
  34. Localization and functional analysis of transposon mutations in regulatory genes of the TOL catabolic pathway.
    J Bacteriol. 1983 May;154(2):676-85 PMID: 6188746
  35. Enzyme recruitment in vitro: use of cloned genes to extend the range of haloaromatics degraded by Pseudomonas sp. strain B13.
    J Bacteriol. 1984 Jun;158(3):1025-32 PMID: 6327621
  36. TOL plasmid can prevent induction of chemotactic responses to aromatic acids.
    J Bacteriol. 1984 Nov;160(2):797-800 PMID: 6501222
Article Info
Journal
Journal of bacteriology
Abbr.
J Bacteriol
ISSN
0021-9193
Published
1987-02-00
Pages
558-64
Language
English
Region
United States
NLM ID
2985120R
PMCID
PMC211814
Subset
IM
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