Initial reactions in the oxidation of 1,2-dihydronaphthalene by Sphingomonas yanoikuyae strains

Applied and Environmental Microbiology

Volumn 62, Issue 12, 1996, Pages 4388-4394

  Eaton, Staci L ^a   Resnick, Sol M ^a   Gibson, David T ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; BACTERIAL METABOLISM; ENANTIOMER; ENZYME SPECIFICITY; FATTY ACID DESATURATION; OXIDATION; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE;

BACTERIA (MICROORGANISMS); SPHINGOBIUM YANOIKUYAE; SPHINGOMONAS;

EID: 0029860364     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.62.12.4388-4394.1996     Document Type: Article

References (42)

1. Agarwal, R., D. R. Boyd, R. A. S. McMordie, G. A. O'Kane, P. Porter, N. D. Sharma, H. Dalton, and D. J. Gray. 1990. Chiral arene hydrates of naphthalene: enzymatic and chemical syntheses. J. Chem. Soc. Chem. Commun. 1990:1711-1713.
2. Allen, C. C. R., D. R. Boyd, H. Dalton, N. D. 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 of either absolute configuration. J. Chem. Soc. Chem. Commun. 1995:117-118.
3. Allen, C. C. R., D. R. Boyd, H. Dalton, N. D. Sharma, S. A. Haughey, R. A. S. McMordie, B. T. McMurray, G. N. Sheldrake, and K. Sproule. 1995. Sulfoxides of high enantiopurity from bacterial dioxygenase-catalyzed oxidation. J. Chem. Soc. Chem. Commun. 1995:119-120.
4. Boyd, D. R., R. A. S. McMordie, N. D. Sharma, H. Dalton, P. Williams, and R. O. Jenkins. 1989. Stereospecific benzylic hydroxylation of bicyclic alkenes by Pseudomonas putida: isolation of (+)-R-1-hydroxy-1,2-dihydronaphthalene, an arene hydrate of naphthalene from metabolism of 1,2-dihydronaphthalene. J. Chem. Soc. Chem. Commun. 1989:339-340.
5. Boyd, D. R., N. D. Sharma, and H. Dalton. 1995. Enzyme-catalyzed hydroxylations of aromatic substrates: stereochemical and mechanistic aspects, p. 130-139. In B. T. Golding, R. J. Griffin, and H. Maskill (ed.), Organic reactivity: physical and biological aspects. The Royal Society of Chemistry, Cambridge.
6. Boyd, D. R., N. D. Sharma, N. A. Kerley, R. A. S. McMordie, G. N. Sheldrake, P. Williams, and H. Dalton. 1996. Dioxygenase-catalyzed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dehydro naphthalenediols. J. Chem. Soc. Perkin Trans. 1 1996:67-74.
7. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
8. Brown, H. C., and J. V. N. Vara Prasad. 1985. Hydroboration-oxidation of 1,4-epoxy-1,4-dihydronaphthalene with and without ring opening. J. Org. Chem. 50:3002-3005.
9. 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. JAI Press, Greenwich, Conn.
10. Carless, H. A. J. 1992. The use of cyclohexa-3,5-diene-1,2-diols in enantio-specific synthesis. Tetrahedron Asymmetry 3:795-826.
11. Cerniglia, C. E., J. Morgan, and D. T. Gibson. 1979. Bacterial and fungal oxidation of dibenzofuran. Biochem. J. 180:175-185.
12. 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.
13. Gibson, D. T., V. Mahadevan, D. M. Jerina, H. Yagi, and H. J. C. Yeh. 1975. Oxidation of the carcinogens benzo[a]pyrene and benzo[a]anthracene to dihydrodiols by a bacterium. Science 189:295-297.
14. Gibson, D. T., S. M. Resnick, K. Lee, J. M. Brand, U. S. Torok, L. P. Wackett, M. J. Schocken, and B. E. Haigler. 1995. Desaturation, dioxygenation and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4. J. Bacteriol. 177:2615-2621.
15. Gibson, D. T., R. L. Roberts, M. C. Wells, and V. M. Kobal. 1973. Oxidation of biphenyl by a Beijerinckia species. Biochem. Biophys. Res. Commun. 50:211-219.
16. Hudlicky, T., and J. W. Reed. 1995. An evolutionary perspective of microbial oxidations of aromatic compounds in enantioselective synthesis: history, current status, and perspectives, p. 271-312. In A. Hassner (ed.), Advances in asymmetric synthesis. JAI Press, Inc., Greenwich, Conn.
17. Jeffrey, A. M., and D. M. Jerina. 1972. Autooxidation of 1,4-dihydronaphthalene. Formation of 3-benzoxepin via pyrolysis of 1,2-dihydronaphthalene 2-hydroperoxide. J. Am. Chem. Soc. 94:4048-4049.
18. Jeffrey, A. M., H. J. C. Yeh, D. M. Jerina, T. R. Patel, J. F. Davey, and D. T. Gibson. 1975. Initial reactions in the oxidation of naphthalene by Pseudomonas putida. Biochemistry 14:575-583.
19. Jerina, D. M., J. W. Daly, A. M. Jeffrey, and D. T. Gibson. 1971. cis-1,2-Dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch. Biochem. Biophys. 142:394-396.
20. Jerina, D. M., H. Selander, H. Yagi, M. C. Wells, J. F. Davey, V. Mahadevan, and D. T. Gibson. 1976. Dihydrodiols from anthracene and phenanthrene. J. Am. Chem. Soc. 98:5988-5996.
21. Jerina, D. M., P. J. Van Bladeren, H. Yagi, D. T. Gibson, V. Mahadevan, A. S. Neese, M. Koreeda, N. D. Sharma, and D. R. Boyd. 1984. Synthesis and absolute configuration of the bacterial cis-1,2-cis-8,9-, and cis-10,11-dihydrodiol metabolites of benz[a]anthracene formed by a strain of Beijerinckia. J. Org. Chem. 49:3621-3628.
22. Khan, A. A., R.-F. Wang, W.-W. Cao, W. Franklin, and C. E. Cerniglia. 1996. Reclassification of a polycyclic aromatic hydrocarbon-metabolizing bacterium, Beijerinckia sp. strain B1, as Sphingomonas yanoikuyae by fatty-acid analysis, protein pattern analysis, DNA-DNA hybridization, and 16S ribosomal DNA sequencing. Int. J. Syst. Bacteriol. 46:466-469.
23. Laborde, A. L., and D. T. Gibson. 1977. Metabolism of dibenzothiophene by a Beijerinckia species. Appl. Environ. Microbiol. 34:783-790.
24. Lee, K., J. M. Brand, and D. T. Gibson. 1995. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem. Biophys. Res. Commun. 212:9-15.
25. Mahaffey, W. R. 1986. Stereoheterotopic metabolism of dibenzothiophene and benz[a]anthracene by Beijerinckia B1. Ph.D. thesis. The University of Texas, Austin.
26. Mahaffey, W. R., D. T. Gibson, and C. E. Cerniglia. 1988. Bacterial oxidation of chemical carcinogens: formation of polycyclic aromatic acids from benz [a]anthracene. Appl. Environ. Microbiol. 54:2415-2423.
27. Patel, T. R., and D. T. Gibson. 1974. Purification and properties of (+)-cis-naphthalene dihydrodiol dehydrogenase of Pseudomonas putida. J. Bacteriol. 119:879-888.
28. Resnick, S. M., and D. T. Gibson. 1993. Biotransformation of anisole and phenetole by aerobic hydrocarbon-oxidizing bacteria. Biodegradation 4:195-203.
29. Resnick, S. M., and D. T. Gibson. 1996. Oxidation of 6,7-dihydro-5H-benzocycloheptene by bacterial strains expressing naphthalene dioxygenase, biphenyl dioxygenase, and toluene dioxygenase yields homochiral monol or cis-diol enantiomers as major products. Appl. Environ. Microbiol. 62:1364-1368.
30. Resnick, S. M., and D. T. Gibson. 1996. Oxidation of polycyclic aromatic compounds and formation of novel cis-diol enantiomers by carbazole-utilizing pseudomonads, abstr. O-11, p. 355. In Abstracts of the 96th General Meeting of the American Society for Microbiology 1996. American Society for Microbiology, Washington, D.C.
31. Resnick, S. M., and D. T. Gibson. Unpublished data.
32. 1H NMR determination of the absolute configuration and enantiomeric excess of bacterial and synthetic cis-diols. J. Org. Chem. 60:3546-3549.
33. Resnick, S. M., D. S. Torok, K. Lee, J. M. Brand, and D. T. Gibson. 1994. Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl. Environ. Microbiol. 60:3323-3328.
34. Rogers, J. E., and D. T. Gibson. 1977. Purification and properties of cis-toluene dihydrodiol dehydrogenase from Pseudomonas putida. J. Bacteriol. 130:1117-1124.
35. Schocken, M. J., and D. T. Gibson. 1984. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Appl. Environ. Microbiol. 48:10-16.
36. 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 commercial manufacture and application of optically active compounds. John Wiley & Sons Ltd., Chichester, United Kingdom.
37. Stanier, R. Y., N. J. Palleroni, and M. Doudoroff. 1966. The aerobic pseudomonads; a taxonomic study. J. Gen. Microbiol. 43:159-271.
38. Stinson, S. C. 1995. Chiral drugs. Chem. Eng. News 73:44-74.
39. Torok, D. S., S. M. Resnick, J. M. Brand, D. L. Cruden, and D. T. Gibson. 1995. Desaturation and oxygenation of 1,2-dihydronaphthalene by toluene and naphthalene dioxygenase. J. Bacteriol. 177:5799-5805.
40. 4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant. Tetrahedron Lett. 23:1973-1976.
41. Wackett, L. P., L. D. Kwart, and D. T. Gibson. 1988. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27:1360-1367.
42. Ziffer, H., K. Kabuto, D. T. Gibson, V. M. Kobal, and D. M. Jerina. 1977. The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes. Tetrahedron 33:2491-2496.