Biotransformation of 6,6-dimethylfulvene by Pseudomonas putida RE213

Applied and Environmental Microbiology

Volumn 62, Issue 3, 1996, Pages 756-760

  Eaton, Richard W ^a,c   Selifonov, Sergey A ^b  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (1 METHYLETHYLIDENE) 3 CYCLOPENTENE 1,2 DIOL; 6,6 DIMETHYLFULVENE; BACTERIAL ENZYME; CUMENE; CYCLOPENTADIENE DERIVATIVE; DIOXYGENASE; OXYGENASE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS PUTIDA;

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

EID: 0029991023     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.62.3.756-760.1996     Document Type: Article

References (46)

1. Allen, C. C. R., D. R. Boyd, H. Dalton, N. Sharma, I. Brannigan, N. A. Kerley, G. N. Sheldrake, and S. C. Taylor. 1995. Enantioselective bacterial biotransformation routes to cis-diol metabolites of monosubstituted benzenes, naphthalene and benzocycloalkenes or either absolute configuration. J. Chem. Soc. Chem. Commun 1995:117-118
2. Borcherding, D. R., S. A. Scholtz, and R. T. Borchardt. 1981. Synthesis of analogues of neoplanocin A: utilization of optically active dihydroxycyclopentenones derived from carbohydrates J. Org. Chem 52:5457-5461.
3. Boyd, D. R., M. R. J. L. Dorrity, M. V. Hand, J. F. Malone, N. D. Sharma, H. Dalton, D. J. Gray, and G. N. Sheldrake. 1991 Enantiomeric excess and absolute configuration determination of cis-dihydrodiols from bacterial metabolism of monocyclic arenes. J. Am Chem. Soc. 113:666-667
4. Boyd, D. R., N. D. Sharma, S. A. Barr, H. Dalton, J. Chima, G. Whited, and R. Seemayer. 1994 Chemoenzymatic synthesis of the 2,3- and 3,4-cis-dihydrodiol enantiomers of monosubstituted benzenes. J. Am. Chem. Soc. 116: 1147-1148.
5. Brown, B. R., and J. A. H. McBride. 1964. New method for assignment of a relative configuration of 2,3-trans-flavan-3,4-diols. J. Chem. Soc. 1964:3822-3831.
6. Brown, S. M., and T. Hudlicky. 1993. The use of arene cis-diols in synthesis, p 113-176. In T. Hudlicky (ed.), Organic synthesis. Theory and applications, vol. 2. JAI Press Inc., Greenwich, Conn.
7. Carless, H. A. J. 1992 The use of cyclohexa-3,5-diene-1,2-diols in enantiospecific synthesis. Tetrahedron Asymmetry 3:795-826.
8. Cocu, F. G., and T. Posternak. 1972. Recherches dans la série des cyclitols XLIV. Synthèses de cycloses dérivés du cyclopentane. Helv. Chim. Acta 55:2838-2844
9. DeFrank, J. J., and D. W. Ribbons. 1976. The p-cymene pathway in Pseudomonas putida PL: isolation and characterization of a dihydrodiol accumulated by a mutant. Biochem. Biophys. Res. Commun. 70:1129-1135.
10. DeFrank, J. J., and D. W. Ribbons. 1977. p-Cymene pathway in Pseudomonas putida: initial reactions. J Bacteriol. 129:1356-1364.
11. Eaton, R. W., and P. J. Chapman. 1992. Bacterial metabolism of naphthalene. construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions. J. Bacteriol 174:7542-7554.
12. Eaton, R. W., and J. Nitterauer. 1994 Biotransformation of benzothiophene by isopropylbenzene-degrading bacteria. J. Bacteriol. 176:3992-4002.
13. Eaton, R. W., and D. W. Ribbons. 1982. Metabolism of dibutylphthalate and phthalate by Micrococcus sp. strain 12B. J. Bacteriol. 151:48-57.
14. Eaton, R. W., and K. N. Timmis. 1986. Characterization of a plasmid-specified pathway for catabolism of isopropylbenzene in Pseudomonas putida RE204. J. Bacteriol. 168:123-131.
15. Engesser, K. H., W. Fietz, P. Fisher, P. Shulte, and H.-J. Knackmuss. 1990. 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. 69:317-322.
16. Ensley, B. D., B. J. Ratzkin, T. D. Osslund, M. J. Simon, L. P. Wackett, and D. T. Gibson. 1983. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Science 222:167-569.
17. Geary, P. J., R. J. Pryce, S. M. Roberts, S. G. Ryback, and J. A. Winders. 1990. The oxidation of norbornadiene and some derivatives using Pseudomonas sp. J. Chem Soc. Chem Commun. 1990:204-205.
18. Gibson, D. T., B. Gschwendt, W. K. Yeh, and V. M. Kobal. 1973. Initial reactions in the oxidation of ethylbenzene by Pseudomonas putida Biochemistry 12:1520-1528.
19. Gibson, D. T., M. Hensley, H. Yoshioka, 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.
20. Gibson, D. T., and V. Subramanian. 1984. Microbial degradation of aromatic hydrocarbons, p. 181-250. In D. T. Gibson (ed.), Microbial degradation of organic compounds. Marcel Dekker, Inc , New York.
21. Hudlicky, T., H. Luna, G. Barbieri, and L. D. Kwart. 1988. Enantioselective synthesis through microbial oxidation of arenes. 1. Efficient preparation of terpene and prostarioid synthons J. Am. Chem. Soc. 110:4735-4741.
22. Hudlicky, T., H. Luna, J. D. Price, and F. Rulin. 1990. Microbial oxidation of chloroaromatics in the enantiodivergent synthesis of pyrrolizidine alkaloids. J. Org. Chem. 55:4683-4687.
23. Illman, D. L. 1994. Environmentally benign chemistry aims for processes that don't pollute Chem Eng. News, 5 September, p. 22-27.
24. 2. J. Am. Chem. Soc. 108:5655-5656.
25. 2 methyl ester. J. Am. Chem Soc. 110:4726-4735
26. Kobal, V. M., D. T. Gibson, R. E. Davis, and A. Garza. 1973. X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene by Pseudomonas putida 39D. J. Am Chem. Soc 95:4420-4421.
27. McCain, G. H. 1958. Anionic exchange resins as catalysts in the preparation of fulvenes. J. Org Chem. 23:632-633.
28. Medich, J. R., K. B. Kunnen, and C. R. Johnson. 1987. Synthesis of the carbocyclic nucleoside (-)-neplanocin A. Tetrahedron Lett. 28:4131-4134
29. Nakatzu, C. H., and R. C. Wyndham. 1993. Cloning and expression of the transposable chlorobenzoate 3,4-dioxygenase genes of Alcaligenes sp. strain BR60. Appl. Environ. Microbiol. 59:3625-3633
30. Ohgi, T., T. Kondo, and T. Goto. 1979. Total synthesis of optically pure nucleoside Q. Determination of absolute stereochemistry of natural nucleoside Q. J. Am. Chem. Soc. 101:3629-3633.
31. Ohrui, H., M. Konno, and H. Meguro. 1987. Synthesis of (4S,5S)4,5-dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one from D-ribose Agric. Biol Chem 51:625-626.
32. Omori, T., M. Matsubara, S. Matsuda, and T. Kodama. 1991. Production of 4,5-dihydro-4,5-dihydroxyphthtalate from phthalate by a mutant strain of Pseudomonas testosteroni M4-1. Appl. Microbiol. Technol. 35:431-435.
33. 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.
34. Ribbons, D. W. 1990. Biotransformations aid organic chemists. Sci Prog (Oxford) 74:205-226.
35. Selifonov, S. A., and R. W. Eaton. Unpublished data.
36. Selifonov, S. A., M. Grifoll, J. E. Gurst, and P. J. Chapman. 1993. Isolation and characterization of (+)cis-1,1a-dihydroxy-1-hydrofluorene-9-one formed by angular dioxygenation in the bacterial catabolism of fluorene. Biochem. Biophys. Res Commun. 193:67-76.
37. Selifonov, S. A., J. E. Gurst, and L. P. Wackett. 1995. Regioselective dioxygenation of ortho-trifluoromethylbenzoate by Pseudomonas aeruginosa 142: evidence for 1,2-dioxygenation as a mechanism in ortho-halobenzoate dehalogenation. Biochem. Biophys. Res. Commun. 213:759-767.
38. Selifonova, O. V., S. A. Selifonov, and R. W. Eaton. 1995 Luciferase expression in bacteria carrying ipb-lux fusions induced by chlorinated solvents, abstr. Q-79 In Abstracts of the 95th General Meeting of the American Society for Microbiology 1995. American Society for Microbiology, Washington, D.C.
39. Sheldon, R. A. 1992. Designing economic chiral syntheses. Manufacturing Chem. August, p 20-25.
40. Sheldrake, G. N. 1992. Biologically derived arene cis-dihydrodiols as synthetic building blocks, p. 127-166. In A N. Collins, G. N. Sheldrake, and J. Crosby (ed.), Chirality in industry - the commerical manufacture and applications of optically active compounds. John Wiley & Sons, Ltd., Chichester, England
41. Stabile, M. R. 1995. Ph.D. thesis. Virginia Polytechnic Institute and State University, Blacksburg.
42. Stinson, S. C. 1994. Chiral drugs. Chem. Eng. News. 19 September, p. 38-72.
43. Verheyden, J. P., A. C. Richardson, R. S. Bhatt, B. D. Grant, W. L. Fitch, and J. G. Moffatt. 1978. Chiral syntheses of the antibiotics anisomycin and pentenomycin from carbohydrates. Pure Appl. Chem. 50:1363-1383.
44. Wackett, L. P., and D. T. Gibson. 1988. Degradation of trichloroethylene by toluene dioxygenase in whole-cell studies with Pseudomonas putida F1. Appl. Environ. Microbiol. 54:1703-1708.
45. Ziffer, H., D. M. Jerina, D. T. Gibson, and V. M. Kobal. 1973. Absolute stereochemistry of the (+)cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene produced from toluene by Pseudomonas putida. J. Am. Chem. Soc. 95:4048-4049.
46. Ziffer, H., K. Kabuto, D. T. Gibson, V. M. Kobal, and D. M. Jerina. 1977. Absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes Tetrahedron 33:2491-2496.