Degradation of Diphenylether by Pseudomonas Cepacia Et4: Enzymatic Release of Phenol from 2,3-dihydroxydiphenylether

Overview

Journal Arch Microbiol

Specialty Microbiology

Date 1993 Jan 1

PMID 7683455

Citations 11

Authors

F Pfeifer

H G Truper

J Klein

S Schacht

Affiliations

Soon will be listed here.

Abstract

2,3-Dihydroxybiphenyl dioxygenase from Pseudomonas cepacia Et 4 was found to catalyze the ring fission of 2,3-dihydroxydiphenylether in the course of diphenylether degradation. The enzyme was purified and characterized. It had a molecular mass of 240 kDa and is dissociated by SDS into eight subunits of equal mass (31 kDa). The purified enzyme was found to be most active with 2,3-dihydroxybiphenyl as substrate and showed moderate activity with 2,3-dihydroxydiphenylether, catechol and some 3-substituted catechols. The Km-value of 1 microM for 2,3-dihydroxydiphenylether indicated a high affinity of the enzyme towards this substrate. The cleavage of 2,3-dihydroxydiphenylether by 2,3-dihydroxybiphenyl dioxygenase lead to the formation of phenol and 2-pyrone-6-carboxylate as products of ring fission and ether cleavage without participation of free intermediates. Isotope labeling experiments carried out with 18O2 and H2(18)O indicated the incorporation of 18O from the atmosphere into the carboxyl residue as well as into the carbonyl oxygen of the lactone moiety of 2-pyrone-6-carboxylate. Based on these experimental findings the reaction mechanism for the formation of phenol and 2-pyrone-6-carboxylate is proposed in accordance with the mechanism suggested by Kersten et al. (1982).

Citing Articles

Degradation of Triclosan in the Water Environment by Microorganisms: A Review.

Yin Y, Wu H, Jiang Z, Jiang J, Lu Z Microorganisms. 2022; 10(9).

PMID: 36144315 PMC: 9505857. DOI: 10.3390/microorganisms10091713.

Biochemical and genetic characterization comparison of four extradiol dioxygenases in Rhizorhabdus wittichii RW1.

Hassan H, D Enza M, Armengaud J, Pieper D Appl Microbiol Biotechnol. 2022; 106(17):5539-5550.

PMID: 35906995 DOI: 10.1007/s00253-022-12099-3.

Degradation of Diphenyl Ether in Sphingobium phenoxybenzoativorans SC_3 Is Initiated by a Novel Ring Cleavage Dioxygenase.

Cai S, Chen L, Ai Y, Qiu J, Wang C, Shi C Appl Environ Microbiol. 2017; 83(10).

PMID: 28283519 PMC: 5411504. DOI: 10.1128/AEM.00104-17.

Microbial degradation of decabromodiphenyl ether (DBDE) in soil slurry microcosms.

Chou H, Hwa M, Lee Y, Chang Y, Chang Y Environ Sci Pollut Res Int. 2015; 23(6):5255-67.

PMID: 26561328 DOI: 10.1007/s11356-015-5767-x.

Characterization of the molecular degradation mechanism of diphenyl ethers by Cupriavidus sp. WS.

Wang S, Bai N, Wang B, Feng Z, Hutchins W, Yang C Environ Sci Pollut Res Int. 2015; 22(21):16914-26.

PMID: 26109219 DOI: 10.1007/s11356-015-4854-3.

References

Pfeifer F, Truper H, Klein J, Schacht S . Degradation of diphenylether by Pseudomonas cepacia Et4: enzymatic release of phenol from 2,3-dihydroxydiphenylether. Arch Microbiol. 1993; 159(4):323-9. DOI: 10.1007/BF00290914. View

CARTWRIGHT N, Smith A . Bacterial attack on phenolic ethers: An enzyme system demethylating vanillic acid. Biochem J. 1967; 102(3):826-41. PMC: 1270334. DOI: 10.1042/bj1020826. View

Fortnagel P, Harms H, Wittich R, Krohn S, Meyer H, Sinnwell V . Metabolism of Dibenzofuran by Pseudomonas sp. Strain HH69 and the Mixed Culture HH27. Appl Environ Microbiol. 1990; 56(4):1148-56. PMC: 184358. DOI: 10.1128/aem.56.4.1148-1156.1990. View

Gamar Y, Gaunt J . Bacterial metabolism of 4-chloro-2-methylphenoxyacetate. Formation of glyoxylate by side-chain cleavage. Biochem J. 1971; 122(4):527-31. PMC: 1176810. DOI: 10.1042/bj1220527. View

Kersten P, DAGLEY S, Whittaker J, Arciero D, Lipscomb J . 2-pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species. J Bacteriol. 1982; 152(3):1154-62. PMC: 221622. DOI: 10.1128/jb.152.3.1154-1162.1982. View

Ribbons D . Stoicheiometry of O-demethylase activity in Pseudomonas aeruginosa. FEBS Lett. 1970; 8(2):101-104. DOI: 10.1016/0014-5793(70)80235-6. View

Bernhardt F, Ruf H, Staudinger H . Pufification of a 4-methoxybenzoate O-demethylase from Pseudomonas putida. Hoppe Seylers Z Physiol Chem. 1971; 352(8):1091-9. DOI: 10.1515/bchm2.1971.352.2.1091. View

Tack B, Chapman P, DAGLEY S . Metabolism of gallic acid and syringic acid by Pseudomonas putida. J Biol Chem. 1972; 247(20):6438-43. View

Taira K, Hayase N, Arimura N, Yamashita S, Miyazaki T, Furukawa K . Cloning and nucleotide sequence of the 2,3-dihydroxybiphenyl dioxygenase gene from the PCB-degrading strain of Pseudomonas paucimobilis Q1. Biochemistry. 1988; 27(11):3990-6. DOI: 10.1021/bi00411a015. View

10.

Laemmli U . Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 1970; 227(5259):680-5. DOI: 10.1038/227680a0. View

11.

Furukawa K, Matsumura F . Microbial metabolism of polychlorinated biphenyls. Studies on the relative degradability of polychlorinated biphenyl components by Alkaligenes sp. J Agric Food Chem. 1976; 24(2):251-6. DOI: 10.1021/jf60204a002. View

12.

Engesser K, Fietz W, Fischer P, Schulte P, Knackmuss H . Dioxygenolytic cleavage of aryl ether bonds: 1,2-dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradation. FEMS Microbiol Lett. 1990; 57(3):317-21. DOI: 10.1016/0378-1097(90)90087-7. View

13.

Gibson D, Roberts R, Wells M, Kobal V . Oxidation of biphenyl by a Beijerinckia species. Biochem Biophys Res Commun. 1973; 50(2):211-9. DOI: 10.1016/0006-291x(73)90828-0. View

14.

Weber K, Osborn M . The reliability of molecular weight determinations by dodecyl sulfate-polyacrylamide gel electrophoresis. J Biol Chem. 1969; 244(16):4406-12. View

15.

Bradford M . A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976; 72:248-54. DOI: 10.1016/0003-2697(76)90527-3. View

16.

Tulp M, Sundstrom G, Martron L, Hutzinger O . Metabolism of chlorodiphenyl ethers and Irgasan DP 300. Xenobiotica. 1979; 9(2):65-77. DOI: 10.3109/00498257909038708. View

17.

Saeki Y, Nozaki M, SENOH S . Cleavage of pyrogallol by non-heme iron-containing dioxygenases. J Biol Chem. 1980; 255(18):8465-71. View

18.

Furukawa K, Arimura N . Purification and properties of 2,3-dihydroxybiphenyl dioxygenase from polychlorinated biphenyl-degrading Pseudomonas pseudoalcaligenes and Pseudomonas aeruginosa carrying the cloned bphC gene. J Bacteriol. 1987; 169(2):924-7. PMC: 211873. DOI: 10.1128/jb.169.2.924-927.1987. View

19.

Catelani D, Colombi A, Sorlini C, Treccani V . Metabolism of biphenyl. 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate: the meta-cleavage product from 2,3-dihydroxybiphenyl by Pseudomonas putida. Biochem J. 1973; 134(4):1063-6. PMC: 1177915. DOI: 10.1042/bj1341063. View

20.

Furukawa K, Miyazaki T . Cloning of a gene cluster encoding biphenyl and chlorobiphenyl degradation in Pseudomonas pseudoalcaligenes. J Bacteriol. 1986; 166(2):392-8. PMC: 214617. DOI: 10.1128/jb.166.2.392-398.1986. View