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. 1974 Sep;119(3):879–888. doi: 10.1128/jb.119.3.879-888.1974

Purification and Propeties of (+)-cis-Naphthalene Dihydrodiol Dehydrogenase of Pseudomonas putida

T R Patel 1, D T Gibson 1
PMCID: PMC245694  PMID: 4369091

Abstract

Cells of Pseudomonas putida, after growth with naphthalene as sole source of carbon and energy, contain an enzyme that oxidizes (+)-cis-1(r),2(s)-dihydroxy-1,2-dihydronaphthalene to 1,2-dihydroxynaphthalene. The purified enzyme has a molecular weight of 102,000 and apparently consists of four 25,500 molecular weight subunits. The enzyme is specific for nicotinamide adenine dinucleotide as an electron acceptor and also oxidizes several other cis-dihydrodiols. However, no enzymatic activity was observed with trans-1,2-dihydronaphthalene, or the K-region cis-dihydrodiols of carcinogenic polycyclic hydrocarbons.

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Selected References

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  1. AYENGAR P. K., HAYAISHI O., NAKAJIMA M., TOMIDA I. Enzymic aromatization of 3,5-cyclohexadiene-1,2-diol. Biochim Biophys Acta. 1959 May;33(1):111–119. doi: 10.1016/0006-3002(59)90504-9. [DOI] [PubMed] [Google Scholar]
  2. Andrews P. Estimation of the molecular weights of proteins by Sephadex gel-filtration. Biochem J. 1964 May;91(2):222–233. doi: 10.1042/bj0910222. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. 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]
  4. CORNER E. D., YOUNG L. Biochemical studies of toxic agents. VII. The metabolism of naphthalene in animals of different species. Biochem J. 1954 Dec;58(4):647–655. doi: 10.1042/bj0580647. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Catterall F. A., Murray K., Williams P. A. The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene. Biochim Biophys Acta. 1971 May 18;237(2):361–364. doi: 10.1016/0304-4165(71)90331-x. [DOI] [PubMed] [Google Scholar]
  6. DAVIS B. J. DISC ELECTROPHORESIS. II. METHOD AND APPLICATION TO HUMAN SERUM PROTEINS. Ann N Y Acad Sci. 1964 Dec 28;121:404–427. doi: 10.1111/j.1749-6632.1964.tb14213.x. [DOI] [PubMed] [Google Scholar]
  7. Daly J. W., Jerina D. M., Witkop B. Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia. 1972 Oct 15;28(10):1129–1149. doi: 10.1007/BF01946135. [DOI] [PubMed] [Google Scholar]
  8. Davies J. I., Evans W. C. Oxidative metabolism of naphthalene by soil pseudomonads. The ring-fission mechanism. Biochem J. 1964 May;91(2):251–261. doi: 10.1042/bj0910251. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. De Frenne E., Eberspächer J., Lingens F. The bacterial degradation of 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone. Eur J Biochem. 1973 Mar 1;33(2):357–363. doi: 10.1111/j.1432-1033.1973.tb02690.x. [DOI] [PubMed] [Google Scholar]
  10. FERNLEY H. N., EVANS W. C. Oxidative metabolism of polycyclic hydrocarbons by soil Pseudomonads. Nature. 1958 Aug 9;182(4632):373–375. doi: 10.1038/182373a0. [DOI] [PubMed] [Google Scholar]
  11. Gibson D. T., Cardini G. E., Maseles F. C., Kallio R. E. Incorporation of oxygen-18 into benzene by Pseudomonas putida. Biochemistry. 1970 Mar 31;9(7):1631–1635. doi: 10.1021/bi00809a024. [DOI] [PubMed] [Google Scholar]
  12. Gibson D. T., Gschwendt B., Yeh W. K., Kobal V. M. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida. Biochemistry. 1973 Apr 10;12(8):1520–1528. doi: 10.1021/bi00732a008. [DOI] [PubMed] [Google Scholar]
  13. Gibson D. T., Hensley M., Yoshioka H., Mabry T. J. Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. Biochemistry. 1970 Mar 31;9(7):1626–1630. doi: 10.1021/bi00809a023. [DOI] [PubMed] [Google Scholar]
  14. 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]
  15. Gibson D. T., Koch J. R., Schuld C. L., Kallio R. E. Oxidative degradation of aromatic hydrocarbons by microorganisms. II. Metabolism of halogenated aromatic hydrocarbons. Biochemistry. 1968 Nov;7(11):3795–3802. doi: 10.1021/bi00851a003. [DOI] [PubMed] [Google Scholar]
  16. Gibson D. T., Roberts R. L., Wells M. C., Kobal V. M. Oxidation of biphenyl by a Beijerinckia species. Biochem Biophys Res Commun. 1973 Jan 23;50(2):211–219. doi: 10.1016/0006-291x(73)90828-0. [DOI] [PubMed] [Google Scholar]
  17. Högn T., Jaenicke L. Benzene metabolism of Moraxella species. Eur J Biochem. 1972 Oct;30(2):369–375. doi: 10.1111/j.1432-1033.1972.tb02107.x. [DOI] [PubMed] [Google Scholar]
  18. Jerina D. M., Daly J. W., Jeffrey A. M., Gibson D. T. Cis-1,2-dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch Biochem Biophys. 1971 Jan;142(1):394–396. doi: 10.1016/0003-9861(71)90298-0. [DOI] [PubMed] [Google Scholar]
  19. Jerina D. M., Daly J. W., Witkop B., Zaltzman-Nirenberg P., Udenfriend S. 1,2-naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene. Biochemistry. 1970 Jan 6;9(1):147–156. doi: 10.1021/bi00803a019. [DOI] [PubMed] [Google Scholar]
  20. Kekwick R. A. The serum proteins in multiple myelomatosis. Biochem J. 1940 Sep;34(8-9):1248–1257. doi: 10.1042/bj0341248. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Kobal V. M., Gibson D. T., Davis R. E., Garza A. X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene by Pseudomonas puida 39-D. J Am Chem Soc. 1973 Jun 27;95(13):4420–4421. doi: 10.1021/ja00794a048. [DOI] [PubMed] [Google Scholar]
  22. LEVY H. B., SOBER H. A. A simple chromatographic method for preparation of gamma globulin. Proc Soc Exp Biol Med. 1960 Jan;103:250–252. doi: 10.3181/00379727-103-25476. [DOI] [PubMed] [Google Scholar]
  23. 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]
  24. MURPHY J. F., STONE R. W. The bacterial dissimilation of naphthalene. Can J Microbiol. 1955 Aug;1(7):579–588. doi: 10.1139/m55-070. [DOI] [PubMed] [Google Scholar]
  25. Oesch F., Daly J. Conversion of naphthalene to trans-naphthalene dihydrodiol: evidence for the presence of a coupled aryl monooxygenase-epoxide hydrase system in hepatic microsomes. Biochem Biophys Res Commun. 1972 Feb 25;46(4):1713–1720. doi: 10.1016/0006-291x(72)90807-8. [DOI] [PubMed] [Google Scholar]
  26. Oesch F., Kaubisch N., Jerina D. M., Daly J. W. Hepatic epoxide hydrase. Structure-activity relationships for substrates and inhibitors. Biochemistry. 1971 Dec 21;10(26):4858–4866. doi: 10.1021/bi00802a005. [DOI] [PubMed] [Google Scholar]
  27. Reiner A. M., Hegeman G. D. Metabolism of benzoic acid by bacteria. Accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. Biochemistry. 1971 Jun 22;10(13):2530–2536. doi: 10.1021/bi00789a017. [DOI] [PubMed] [Google Scholar]
  28. Reiner A. M. Metabolism of aromatic compounds in bacteria. Purification and properties of the catechol-forming enzyme, 3,5-cyclohexadiene-1,2-diol-1-carboxylic acid (NAD + ) oxidoreductase (decarboxylating). J Biol Chem. 1972 Aug 25;247(16):4960–4965. [PubMed] [Google Scholar]
  29. Reiner A. M. Metabolism of benzoic acid by bacteria: 3,5-cyclohexadiene-1,2-diol-1-carboxylic acid is an intermediate in the formation of catechol. J Bacteriol. 1971 Oct;108(1):89–94. doi: 10.1128/jb.108.1.89-94.1971. [DOI] [PMC free article] [PubMed] [Google Scholar]
  30. SCHEIDEGGER J. J. Une micro-méthode de l'immuno-electrophorèse. Int Arch Allergy Appl Immunol. 1955;7(2):103–110. [PubMed] [Google Scholar]
  31. Stanier R. Y., Palleroni N. J., Doudoroff M. The aerobic pseudomonads: a taxonomic study. J Gen Microbiol. 1966 May;43(2):159–271. doi: 10.1099/00221287-43-2-159. [DOI] [PubMed] [Google Scholar]
  32. TRECCANI V., WALKER N., WILTSHIRE G. H. The metabolism of naphthalene by soil bacteria. J Gen Microbiol. 1954 Dec;11(3):341–348. doi: 10.1099/00221287-11-3-341. [DOI] [PubMed] [Google Scholar]
  33. Van Heyningen R., Pirie A. The metabolism of naphthalene and its toxic effect on the eye. Biochem J. 1967 Mar;102(3):842–852. doi: 10.1042/bj1020842. [DOI] [PMC free article] [PubMed] [Google Scholar]
  34. WALKER N., WILTSHIRE G. H. The breakdown of naphthalene by a soil bacterium. J Gen Microbiol. 1953 Apr;8(2):273–276. doi: 10.1099/00221287-8-2-273. [DOI] [PubMed] [Google Scholar]
  35. Weber K., Osborn M. The reliability of molecular weight determinations by dodecyl sulfate-polyacrylamide gel electrophoresis. J Biol Chem. 1969 Aug 25;244(16):4406–4412. [PubMed] [Google Scholar]
  36. Ziffer H., Jerina D. M., Gibson D. T., Kobal V. M. Absolute stereochemistry of the (+)-cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene produced from toluene by Pseudomonas putida. J Am Chem Soc. 1973 Jun 13;95(12):4048–4049. doi: 10.1021/ja00793a036. [DOI] [PubMed] [Google Scholar]

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