Stereochemical course of two arene-cis-diol dehydrogenases specifically induced in Pseudomonas putida

Journal of Bacteriology

Volumn 179, Issue 12, 1997, Pages 4023-4029

  Morawski, Birgit ^a   Casy, Guy ^b   Illaszewicz, Carina ^a   Griengl, Herfried ^a   Ribbons, Douglas W ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; POLYCYCLIC AROMATIC HYDROCARBON; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

AROMATIZATION; ARTICLE; BACTERIAL METABOLISM; DIASTEREOISOMER; DNA SEQUENCE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS PUTIDA; STEREOCHEMISTRY;

ARENE; BACTERIA (MICROORGANISMS); PSEUDOMONAS; PSEUDOMONAS PUTIDA;

EID: 0030962131     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.179.12.4023-4029.1997     Document Type: Article

References (40)

1. Ahmed, S. 1991. PhD. thesis. Imperial College London, London, United Kingdom.
2. Assinder, S. J., and P. R. Williams. 1990. The TOL plasmids: determinants of the catabolism of toluene and the xylenes. Adv. Microb. Physiol. 31:1-70.
3. Axcell, B. C., and P. J. Geary. 1973. The metabolism of benzene by bacteria: purification and some properties of the enzyme cis-1,2-dihydrocyclohexa-3,5-diene (nicotinamide adeninedinucleotide) oxidoreductase (cis-benzeneglycoldehydrogenase) Biochem. J. 136:927-934.
4. Benner, S. A., A. Glasfield, and J. A. Piccirilli. 1989. Stereospecificity in enzymology: its place in evolution. Top. Stereochem. 19:127-207.
5. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye bindding. Anal. Biochem. 72:248-254.
6. DeFrank, J., and D. W. Ribbons. 1977. p-Cymene pathway in Pseudomonas putida: initial reactions. J. Bacteriol. 129:1356-1364.
7. Ferguson, L. N., and A. I. Wims. 1960. Selective oxidation of alkyl groups. J. Org. Chem. 25:668-670.
8. Furukawa, K., N. Arimura, and T. Miyazaki. 1987. Nucleotide sequence of 2,3-dihydroxybiphenyl dioxygenase gene of Pseudomonas pseudoalcaligenes. J. Bacteriol. 169:427-429.
9. Gabriel, O., and D. M. Gersten. 1992. Detection of enzymatic activity after polyacrylamide gel electrophoresis and agarose gel isoelectric focusing, 217-251. In R. Eisenthal and M. J. Danson (ed.), Enzyme assays: a practical approach. Oxford University Press, Oxford, United Kingdom.
10. Gibson, D. T., M. Hensley, H. Yoshiuka, and T. J. Mabry. 1970. Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida. Biochemistry 9:1626-1630.
11. Gibson, D. T. 1971. The microbial oxidation of aromatic hydrocarbons. Crit. Rev. Microbiol. 1:199-223.
12. Gibson, D. T., J. Kock, C. Schuld, and R. E. Kallio. 1968. Oxidative degradation of aromatic hydrocarbons by microorganisms. II. Metabolism of halogenated aromatic hydrocarbons. Biochemistry 7:3795-3801.
13. Gibson, D. T., J. Kock, and R. E. Kallio. 1968. Oxidative degradation of aromatic hydrocarbons by microorganisms. I. Enzymatic formation of catechol from benzene. Biochemistry 7:2653-2662.
14. Gibson, D. T., and V. T. Subramarian. 1984. Degradation of aromatic hydrocarbons. 181-252. In D. T. Gibson (ed.), Microbial degradation of organic compounds. Marcel Dekker, New York, N.Y.
15. Gibson, D. T., and V. M. Kobal. 1973. The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes. Tetrahedron 33:2491-2496.
16. Harayama, S., P. R. Lehrbach, and K. N. Timmis. 1984. Transposon mutagenesis analysis of meta-cleavage pathway operon genes of the TOL plasmid of Pseudomonas putida mt-2. J. Bacteriol. 160:251-255.
17. Hayaishi, O. 1966. Enzymic studies on the mechanism of double hydroxylations. Pharmacol. Rev. 18:71-75.
18. Jenkins, G. N., D. W. Ribbons, D. A. Widdowson, A. M. Z. Slawin, and D. J. Williams. 1995. Synthetic application of biotransformations: absolute stereochemistry and Diels-Alder reactions of the (1S, 2R)-1,2-dihydrocyclohexa-3,5-diene-1-carboxylic acid from Pseudomonas putida. J. Chem. Soc. Perkin Trans. 1:2647-2655.
19. Jörnvall, H., M. Persson, and J. Jeffrey. 1981. Alcohol and polyol dehydrogenases are both divided into two protein types, and structural properties cross-relate the different enzyme activities within each type. Proc. Natl. Acad. Sci. USA 78:4226-4230.
20. Klinmann, J. P. 1972. The mechanism of enzyme-catalyzed reduced nicotinamide adenine dinucleotide-dependent reductions. J. Biol. Chem. 24: 7977-7987.
21. Kobal, V. M., D. T. Gibson, R. E. Davis, and A. Garza. 1973. X-ray determination of the absolute stereochemistry of initial oxidation product formed from toluene by Pseudomonas putida 39/D. J. Am. Chem. Soc. 95:4420-4421.
22. Laird, A. J., D. W. Ribbons, G. C. Woodrow, and I. G. Young. 1980. Bacteriophage Mu-mediated gene transposition and in vitro cloning of the enterochelin gene cluster of Escherichia coli. Gene 11:347-357.
23. Neidle, E. L., M. K. Shapiro, and L. N. Ornston. 1987. Cloning and expression in Escherichia coli of Acinetobacter calcoaceticus genes for benzoate degradation. J. Bacteriol. 169:5496-5503.
24. Oppenheimer, N. J., L. J. Arnold, Jr., and N. O. Kaplan. 1978. Stereospecificity of the intramolecular association of reduced pyridine coenzymes. Biochemistry 17:2613-2619.
25. Patel, R. T., and D. T. Gibson. 1974. Purification and properties of (+)-cis-naphthalene dihydrodiol dehydrogenase of Pseudomonas putida. J. Bacteriol. 119:879-888.
26. Persson, B., M. Krook, and H. Jörnvall. 1991. Characteristics of short-chain alcohol dehydrogenases and related enzymes. FEBS Lett. 200:537-543.
27. Popjak, G. 1970. Stereospecificity of enzymic reactions, p. 115-215. In P. D. Bover (ed.), The enzymes, vol. 3. Academic Press, New York, N.Y.
28. Reiner, A. M., and G. D. Hegeman, 1971. Metabolism of benzoic acid by bacteria: accumulation of (-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by a mutant strain of Alcaligenes eutrophus. Biochemistry 10:2530-2536.
29. +) oxidoreductase (decarboxylating). J. Biol. Chem. 247:4960-4965.
30. Ribbons, D. W., Y. Ohta, and I. J. Higgins. 1972. Electron transport in a flavoprotein, orcinol hydroxylase. Miami Winter Symp. 4:251-274.
31. Rogers, J. E., and D. T. Gibson. 1977. Purification and properties of cis-toluene dihydrodiol dehydrogenase from Pseudomonas putida. J. Bacteriol. 130:1117-1124.
32. Sakaitani, M., F. Rusnak, N. R. Quinn, C. Tu, T. B. Frigo, G. H. Berchthold, and C. T. Walsh. 1990. Mechanistic studies on trans-2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (Ent A) in the biosynthesis of the iron chelator enterobactin. Biochemistry 29:6789-6798.
33. Sarma, R. H., and N. O. Kaplan. 1970. High frequency nuclear magnetic resonance study of the M and P helices of reduced pyridine dinucleotides. Biochemistry 9:539-548.
34. Schläfli, H. R., P. B. Darren, T. Leisinger, and A. M. Cook. 1995. Stereospecificity of hydride removal from NADH by reductases of multicomponent nonheme iron oxygenase systems. J. Bacteriol. 177:831-834.
35. Taylor, S. J. C., D. W. Ribbons, A. M. Z. Slawin, D. A. Widdowson, and D. J. Williams. 1987. Biochemically generated chiral intermediates for organic synthesis: the absolute stereochemistry of 4-bromo-cis-2,3-dihydrocyclohexa-4,6-diene-1-carboxylic acid formed from 4-bromobenzoic acid by a mutant of Pseudomonas putida. Tetrahedron Lett. 28:6391-6392.
36. Wong, C.-H., and G. M. Whitesides. 1994. Tetrahedron organic chemistry series, 1st ed., vol. 12. Enzymes in synthetic organic chemistry. Pergamon Press, Elmsford, N.Y.
37. You, K., L. J. Arnold, Jr., and N. O. Kaplan. 1977. The stereospecificity of bacterial external flavoprotein monooxygenase for nicotinamide adenine dinucleotide. Arch. Biochem. Biophys. 180:550-554.
38. You, K., L. J. Arnold, Jr., W. S. Allison, and N. O. Kaplan. 1978. Enzyme stereospecificities of nicotinamidc nucleotide. Trends Biochem. Sci. 3:265-268.
39. You, K. 1982. Stereospecificities of the pyridine nucleotide linked enzymes. Methods Enzymol. 87:101-126.
40. Zylstra, G. J., and D. T. Gibson. 1989. Toluene degradation by Pseudomonas putida F1. Nucleotide sequence of the tod C1C2BADE genes and their expression in Escherichia coli. J. Biol. Chem. 264:14940-14946.