Home LiteratureArticle Details
PMID: 7765837 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. Review

On the origins and functions of the enzymes of the 4-chlorobenzoate to 4-hydroxybenzoate converting pathway.

Biodegradation ·Vol. 5 ·No. 3-4 ·1994-12-00 ·Pages 259-76

Dunaway-Mariano D, Babbitt PC

Abstract

This review examines the enzymes of 4-chlorobenzoate to 4-hydroxybenzoate converting pathway found in certain soil bacteria. This pathway consists of three enzymes: 4-chlorobenzoate: Coenzyme A ligase, 4-chlorobenzoyl-Coenzyme A dehalogenase and 4-hydroxybenzoyl-Coenzyme A thioesterase. Recent progress made in the cloning and expression of the pathway genes from assorted bacterial strains is described. Gene order and sequence found among these strains are compared to reveal independent enzyme recruitment strategies. Sequence alignments made between the Pseudomonas sp. strain CBS3 4-chlorobenzoate pathway enzymes and structurally related proteins contained within the protein sequence data banks suggest possible origins in preexisting beta-oxidation pathways. The purification and characterization of the physical and kinetic properties of the pathway enzymes are described. Where possible a comparison of these properties between like enzymes from different bacterial sources are made.

MeSH Terms
Amino Acid Sequence Biodegradation, Environmental Chlorobenzoates/metabolism Coenzyme A Ligases/genetics,metabolism Hydrolases/genetics,metabolism Molecular Sequence Data Parabens/metabolism Pseudomonas/enzymology,genetics Sequence Homology, Amino Acid Thiolester Hydrolases/genetics,metabolism
Chemicals
Chlorobenzoates Parabens Hydrolases 4-hydroxybenzoyl-CoA hydrolase Thiolester Hydrolases 4-chlorobenzoyl coenzyme A dehalogenase 4-halobenzoate-CoA ligase Coenzyme A Ligases 4-chlorobenzoic acid 4-hydroxybenzoic acid
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Dunaway-Mariano D
Department of Chemistry and Biochemistry, University of Maryland, College Park 20742.
Babbitt P C
References (87)
87 references, click to expand
  1. Molecular cloning and sequence analysis of the cDNA for rat mitochondrial enoyl-CoA hydratase. Structural and evolutionary relationships linked to the bifunctional enzyme of the peroxisomal beta-oxidation system.
    Eur J Biochem. 1989 Oct 20;185(1):73-8 PMID: 2806264
  2. Bacterial dehalogenation of chlorobenzoates and coculture biodegradation of 4,4'-dichlorobiphenyl.
    Appl Environ Microbiol. 1989 Apr;55(4):887-92 PMID: 2499257
  3. Incorporation of [18O]water into 4-hydroxybenzoic acid in the reaction of 4-chlorobenzoate dehalogenase from pseudomonas spec. CBS 3.
    Biochem Biophys Res Commun. 1984 Oct 15;124(1):178-82 PMID: 6497878
  4. Complete nucleotide sequences and comparison of the structural genes of two 2-haloalkanoic acid dehalogenases from Pseudomonas sp. strain CBS3.
    J Bacteriol. 1991 Feb;173(4):1530-5 PMID: 1995594
  5. Cloning and sequencing of a bile acid-inducible operon from Eubacterium sp. strain VPI 12708.
    J Bacteriol. 1990 Dec;172(12):7011-9 PMID: 2254270
  6. Cloning and sequence analysis of cDNA for luciferase of a Japanese firefly, Luciola cruciata.
    Gene. 1989 Apr 30;77(2):265-70 PMID: 2473944
  7. Cloning and disruption of a gene required for growth on acetate but not on ethanol: the acetyl-coenzyme A synthetase gene of Saccharomyces cerevisiae.
    Yeast. 1992 Dec;8(12):1043-51 PMID: 1363452
  8. Gramicidin S biosynthesis operon containing the structural genes grsA and grsB has an open reading frame encoding a protein homologous to fatty acid thioesterases.
    J Bacteriol. 1989 Oct;171(10):5422-9 PMID: 2477357
  9. Isolation and characterization of the three polypeptide components of 4-chlorobenzoate dehalogenase from Pseudomonas sp. strain CBS-3.
    Biochemistry. 1992 Jun 23;31(24):5605-10 PMID: 1610806
  10. Primary sequence of the Escherichia coli fadBA operon, encoding the fatty acid-oxidizing multienzyme complex, indicates a high degree of homology to eucaryotic enzymes.
    J Bacteriol. 1990 Nov;172(11):6459-68 PMID: 1699931
  11. N-terminal halves of gramicidin S synthetase 1, and tyrocidine synthetase 1 as novel members of firefly luciferase family.
    Protein Seq Data Anal. 1990 Dec;3(6):517-21 PMID: 2089378
  12. Microbial degradation of biphenyl and its derivatives.
    Adv Appl Microbiol. 1992;37:135-64 PMID: 1642156
  13. cDNA cloning of mitochondrial delta 3, delta 2-enoyl-CoA isomerase of rat liver.
    Biochim Biophys Acta. 1992 Feb 28;1130(1):109-12 PMID: 1543742
  14. [Degradation of 4-chlorobenzoic acid by an Arthrobacter species (author's transl)].
    Arch Microbiol. 1976 Nov 2;110(23):253-6 PMID: 1015950
  15. The cyclic peptide synthetase catalyzing HC-toxin production in the filamentous fungus Cochliobolus carbonum is encoded by a 15.7-kilobase open reading frame.
    J Biol Chem. 1992 Dec 25;267(36):26044-9 PMID: 1281482
  16. Cloning and expression of the Arthrobacter globiformis KZT1 fcbA gene encoding dehalogenase (4-chlorobenzoate-4-hydroxylase) in Escherichia coli.
    FEMS Microbiol Lett. 1991 Jun 15;65(2):165-9 PMID: 1884992
  17. Sequence and transcription mapping of Bacillus subtilis competence genes comB and comA, one of which is related to a family of bacterial regulatory determinants.
    J Bacteriol. 1989 Oct;171(10):5362-75 PMID: 2507523
  18. Structural comparison, modes of expression, and putative cis-acting elements of the two 4-coumarate: CoA ligase genes in potato.
    J Biol Chem. 1991 May 5;266(13):8551-9 PMID: 2022667
  19. Cloning, sequence analysis, and functional expression of the acetyl coenzyme A synthetase gene from Methanothrix soehngenii in Escherichia coli.
    J Bacteriol. 1991 Oct;173(20):6383-9 PMID: 1680850
  20. Systematic sequencing of the Escherichia coli genome: analysis of the 0-2.4 min region.
    Nucleic Acids Res. 1992 Jul 11;20(13):3305-8 PMID: 1630901
  21. Nucleotide sequence of a cluster of Escherichia coli enterobactin biosynthesis genes: identification of entA and purification of its product 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase.
    J Bacteriol. 1989 Feb;171(2):791-8 PMID: 2521622
  22. Molecular cloning and expression in Escherichia coli of a cDNA clone encoding luciferase of a firefly, Luciola lateralis.
    Biochim Biophys Acta. 1992 Jun 15;1131(2):161-5 PMID: 1610896
  23. Enzymic Dehalogenation of 4-Chlorobenzoyl Coenzyme A in Acinetobacter sp. Strain 4-CB1.
    Appl Environ Microbiol. 1992 Apr;58(4):1385-7 PMID: 16348702
  24. Firefly luciferase gene: structure and expression in mammalian cells.
    Mol Cell Biol. 1987 Feb;7(2):725-37 PMID: 3821727
  25. Purification and properties of 4-halobenzoate-coenzyme A ligase from Pseudomonas sp. CBS3.
    Biol Chem Hoppe Seyler. 1992 Oct;373(10):1001-7 PMID: 1418673
  26. Molecular cloning and sequencing of cDNA encoding the phosphatidylinositol kinase from rat brain.
    J Biol Chem. 1991 Sep 15;266(26):17580-3 PMID: 1654331
  27. Identification and molecular characterization of the acetyl coenzyme A synthetase gene (acoE) of Alcaligenes eutrophus.
    J Bacteriol. 1992 Oct;174(20):6590-9 PMID: 1356967
  28. Complementary DNA coding click beetle luciferases can elicit bioluminescence of different colors.
    Science. 1989 May 12;244(4905):700-2 PMID: 2655091
  29. Cloning of Pseudomonas sp. strain CBS3 genes specifying dehalogenation of 4-chlorobenzoate.
    J Bacteriol. 1986 Oct;168(1):81-5 PMID: 3759912
  30. Primary structures and catalytic properties of isoenzymes encoded by the two 4-coumarate: CoA ligase genes in parsley.
    Eur J Biochem. 1988 Oct 1;176(3):661-7 PMID: 3169018
  31. Evidence for 4-chlorobenzoic acid dehalogenation mediated by plasmids related to pSS50.
    Appl Environ Microbiol. 1992 Jan;58(1):399-402 PMID: 1539985
  32. Structure and regulation of rat long-chain acyl-CoA synthetase.
    J Biol Chem. 1990 May 25;265(15):8681-5 PMID: 2341402
  33. Novel aerobic 2-aminobenzoate metabolism. Purification and characterization of 2-aminobenzoate-CoA ligase, localisation of the gene on a 8-kbp plasmid, and cloning and sequencing of the gene from a denitrifying Pseudomonas sp.
    Eur J Biochem. 1992 Apr 15;205(2):721-7 PMID: 1315272
  34. Sequence organization and regulation of the Bacillus subtilis menBE operon.
    J Bacteriol. 1992 Aug;174(15):5063-71 PMID: 1629163
  35. The multifunctional peptide synthetase performing the first step of penicillin biosynthesis in Penicillium chrysogenum is a 421,073 dalton protein similar to Bacillus brevis peptide antibiotic synthetases.
    EMBO J. 1990 Sep;9(9):2743-50 PMID: 2118102
  36. DNA sequence determination and functional characterization of the OCT-plasmid-encoded alkJKL genes of Pseudomonas oleovorans.
    Mol Microbiol. 1992 Nov;6(21):3121-36 PMID: 1453953
  37. Microbial breakdown of halogenated aromatic pesticides and related compounds.
    FEMS Microbiol Rev. 1992 Sep;9(1):29-71 PMID: 1389314
  38. Nucleotide sequence of 5' portion of srfA that contains the region required for competence establishment in Bacillus subtilus.
    Nucleic Acids Res. 1993 Jan 11;21(1):93-7 PMID: 8441623
  39. Degradation of 4-chlorophenylacetic acid by a Pseudomonas species.
    J Bacteriol. 1981 Apr;146(1):64-8 PMID: 7217006
  40. Primary structures of the genes, faoA and faoB, from Pseudomonas fragi B-0771 which encode the two subunits of the HDT multienzyme complex involved in fatty acid beta-oxidation.
    J Biochem. 1992 Jan;111(1):8-15 PMID: 1607366
  41. Amino acid sequence similarities of the mitochondrial short chain delta 3, delta 2-enoyl-CoA isomerase and peroxisomal multifunctional delta 3, delta 2-enoyl-CoA isomerase, 2-enoyl-CoA hydratase, 3-hydroxyacyl-CoA dehydrogenase enzyme in rat liver. The proposed occurrence of isomerization and hydration in the same catalytic domain of the multifunctional enzyme.
    J Biol Chem. 1991 Jun 15;266(17):10750-3 PMID: 2040594
  42. Ancestry of the 4-chlorobenzoate dehalogenase: analysis of amino acid sequence identities among families of acyl:adenyl ligases, enoyl-CoA hydratases/isomerases, and acyl-CoA thioesterases.
    Biochemistry. 1992 Jun 23;31(24):5594-604 PMID: 1351742
  43. Identification of genes involved in utilization of acetate and acetoin in Bacillus subtilis.
    Mol Microbiol. 1993 Oct;10(2):259-71 PMID: 7934817
  44. Sequence and analysis of the genetic locus responsible for surfactin synthesis in Bacillus subtilis.
    Mol Microbiol. 1993 May;8(5):821-31 PMID: 8355609
  45. Chlorinated biphenyl mineralization by individual populations and consortia of freshwater bacteria.
    Appl Environ Microbiol. 1990 Jul;56(7):2036-45 PMID: 2117875
  46. A regulatory gene, angR, of the iron uptake system of Vibrio anguillarum: similarity with phage P22 cro and regulation by iron.
    Gene. 1990 Jan 31;86(1):45-51 PMID: 2311935
  47. Microbial transformations of herbicides and pesticides.
    Adv Appl Microbiol. 1991;36:1-66 PMID: 1877379
  48. Isolation of a Saccharomyces cerevisiae long chain fatty acyl:CoA synthetase gene (FAA1) and assessment of its role in protein N-myristoylation.
    J Cell Biol. 1992 May;117(3):515-29 PMID: 1572893
  49. Cloning and sequence analysis of genes for dehalogenation of 4-chlorobenzoate from Arthrobacter sp. strain SU.
    Appl Environ Microbiol. 1992 Dec;58(12):4068-71 PMID: 1476446
  50. Molecular cloning and nucleotide sequence of the cDNA for rat peroxisomal enoyl-CoA: hydratase-3-hydroxyacyl-CoA dehydrogenase bifunctional enzyme.
    J Biol Chem. 1985 Jul 25;260(15):8905-10 PMID: 4019459
  51. Plasmid-mediated mineralization of 4-chlorobiphenyl.
    J Bacteriol. 1985 Sep;163(3):882-9 PMID: 2993249
  52. Characterization of the mmsAB operon of Pseudomonas aeruginosa PAO encoding methylmalonate-semialdehyde dehydrogenase and 3-hydroxyisobutyrate dehydrogenase.
    J Biol Chem. 1992 Jul 5;267(19):13585-92 PMID: 1339433
  53. Characterization of the Cephalosporium acremonium pcbAB gene encoding alpha-aminoadipyl-cysteinyl-valine synthetase, a large multidomain peptide synthetase: linkage to the pcbC gene as a cluster of early cephalosporin biosynthetic genes and evidence of multiple functional domains.
    J Bacteriol. 1991 Apr;173(7):2354-65 PMID: 1706706
  54. Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalysing N-methyldepsipeptide formation in Fusarium scirpi.
    Mol Microbiol. 1993 Mar;7(6):905-14 PMID: 8483420
  55. Nucleotide sequence of a gene from Phanerochaete chrysosporium that shows homology to the facA gene of Aspergillus nidulans.
    DNA Seq. 1992;2(5):319-23 PMID: 1352996
  56. Molecular cloning and nucleotide sequence of the gramicidin S synthetase 1 gene.
    J Biochem. 1989 Oct;106(4):639-45 PMID: 2691508
  57. Human long-chain acyl-CoA synthetase: structure and chromosomal location.
    J Biochem. 1992 Jan;111(1):123-8 PMID: 1607358
  58. Degradation of 4-Chlorobenzoate by Facultatively Alkalophilic Arthrobacter sp. Strain SB8.
    Appl Environ Microbiol. 1989 Feb;55(2):478-82 PMID: 16347854
  59. Biosynthesis of D-alanyl-lipoteichoic acid: cloning, nucleotide sequence, and expression of the Lactobacillus casei gene for the D-alanine-activating enzyme.
    J Bacteriol. 1992 Jul;174(14):4707-17 PMID: 1385594
  60. Biosynthesis of the Escherichia coli siderophore enterobactin: sequence of the entF gene, expression and purification of EntF, and analysis of covalent phosphopantetheine.
    Biochemistry. 1991 Mar 19;30(11):2916-27 PMID: 1826089
  61. Expression of the 4-chlorobenzoate dehalogenase genes from Pseudomonas sp.-CBS3 in Escherichia coli and identification of the gene translation products.
    Can J Microbiol. 1992 Oct;38(10):1074-83 PMID: 1477786
  62. Specificity of 4-chlorobenzoyl coenzyme A dehalogenase catalyzed dehalogenation of halogenated aromatics.
    Biochemistry. 1993 Nov 16;32(45):12245-50 PMID: 8218302
  63. Comparison and cross-species expression of the acetyl-CoA synthetase genes of the Ascomycete fungi, Aspergillus nidulans and Neurospora crassa.
    Mol Microbiol. 1990 Mar;4(3):451-60 PMID: 1972535
  64. Four homologous domains in the primary structure of GrsB are related to domains in a superfamily of adenylate-forming enzymes.
    Mol Microbiol. 1992 Feb;6(4):529-46 PMID: 1560782
  65. Nucleotide sequence of rice 4-coumarate:CoA ligase gene, 4-CL.1.
    Nucleic Acids Res. 1990 Oct 25;18(20):6144 PMID: 2235510
  66. Oxidation and dehalogenation of 4-chlorophenylacetate by a two-component enzyme system from Pseudomonas sp. strain CBS3.
    J Bacteriol. 1984 Nov;160(2):618-21 PMID: 6501216
  67. Genetic control of degradation of chlorinated benzoic acids in Arthrobacter globiformis, Corynebacterium sepedonicum and Pseudomonas cepacia strains.
    FEMS Microbiol Lett. 1991 Jun 15;65(2):171-6 PMID: 1884993
  68. The cephamycin biosynthetic genes pcbAB, encoding a large multidomain peptide synthetase, and pcbC of Nocardia lactamdurans are clustered together in an organization different from the same genes in Acremonium chrysogenum and Penicillium chrysogenum.
    Mol Microbiol. 1991 May;5(5):1125-33 PMID: 1956290
  69. Degradation of halogenated aromatic compounds.
    Biodegradation. 1990;1(2-3):207-20 PMID: 1368148
  70. Characteristics and restriction analysis of the 4-chlorobiphenyl catabolic plasmid, pSS50.
    Appl Environ Microbiol. 1989 May;55(5):1286-8 PMID: 2757383
  71. Cloning and functional expression of a novel long-chain acyl-CoA synthetase expressed in brain.
    J Biochem. 1992 Feb;111(2):197-203 PMID: 1569043
  72. The cluster of penicillin biosynthetic genes. Identification and characterization of the pcbAB gene encoding the alpha-aminoadipyl-cysteinyl-valine synthetase and linkage to the pcbC and penDE genes.
    J Biol Chem. 1990 Sep 25;265(27):16358-65 PMID: 2129535
  73. Delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine synthetase from Aspergillus nidulans. Molecular characterization of the acvA gene encoding the first enzyme of the penicillin biosynthetic pathway.
    J Biol Chem. 1991 Jul 5;266(19):12646-54 PMID: 2061333
  74. A bacterial homolog to the mitochondrial enoyl-CoA hydratase.
    Gene. 1991 Oct 30;107(1):171-2 PMID: 1743516
  75. Identification and characterization of phosphinothricin-tripeptide biosynthetic genes in Streptomyces viridochromogenes.
    Gene. 1992 Jun 15;115(1-2):127-32 PMID: 1612426
  76. Involvement of plasmids in total degradation of chlorinated biphenyls.
    Appl Environ Microbiol. 1982 Sep;44(3):619-26 PMID: 6814360
  77. 2-Haloacid dehalogenase from a 4-chlorobenzoate-degrading Pseudomonas spec. CBS 3.
    Hoppe Seylers Z Physiol Chem. 1983 May;364(5):529-35 PMID: 6873881
  78. Novel enzymic hydrolytic dehalogenation of a chlorinated aromatic.
    Science. 1991 Jul 12;253(5016):182-5 PMID: 1853203
  79. Automatic generation of primary sequence patterns from sets of related protein sequences.
    Proc Natl Acad Sci U S A. 1990 Jan;87(1):118-22 PMID: 2296575
  80. Menaquinone (vitamin K2) biosynthesis: nucleotide sequence and expression of the menB gene from Escherichia coli.
    J Bacteriol. 1992 Aug;174(15):5057-62 PMID: 1629162
  81. Cloning, sequencing, and expression of the fadD gene of Escherichia coli encoding acyl coenzyme A synthetase.
    J Biol Chem. 1992 Dec 15;267(35):25513-20 PMID: 1460045
  82. Nucleotide sequence of the Escherichia coli entE gene.
    FEMS Microbiol Lett. 1989 May;50(1-2):15-9 PMID: 2525505
  83. Degradation of 4-Chlorobenzoic Acid by Arthrobacter sp.
    Appl Environ Microbiol. 1984 Nov;48(5):1020-5 PMID: 16346660
  84. Complete nucleotide sequence of the tycA gene coding the tyrocidine synthetase 1 from Bacillus brevis.
    Nucleic Acids Res. 1988 Dec 23;16(24):11841 PMID: 3267240
  85. Enzymatic dehalogenation of 4-chlorobenzoate by extracts from Arthrobacter sp. SU DSM 20407.
    Biol Chem Hoppe Seyler. 1988 Jul;369(7):567-71 PMID: 3223988
  86. The nucleotide sequence for a proline-activating domain of gramicidin S synthetase 2 gene from Bacillus brevis.
    J Biochem. 1991 Jul;110(1):111-9 PMID: 1939016
  87. Nucleotide sequence of the LYS2 gene of Saccharomyces cerevisiae: homology to Bacillus brevis tyrocidine synthetase 1.
    Gene. 1991 Feb 1;98(1):141-5 PMID: 2013406
Article Info
Journal
Biodegradation
Abbr.
Biodegradation
ISSN
0923-9820
DOI
10.1007/BF00696464
Published
1994-12-00
Pages
259-76
Language
English
Region
Netherlands
NLM ID
9100834
Grants
NIGMS NIH HHS · GM 28688 · United States
External Links
PubMed source DOI: 10.1007/BF00696464 View journal details
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: product@genelibs.com

Copyright © 2026.Genelibs Jinan Honghui Biotechnology Co., Ltd. 鲁ICP备20007159号-2