메뉴 건너뛰기




Volumn 62, Issue 4, 1996, Pages 1364-1368

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

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; NAPHTHALENE DERIVATIVE; TOLUENE DERIVATIVE;

EID: 0029879304     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.62.4.1364-1368.1996     Document Type: Article
Times cited : (26)

References (36)
  • 2
    • 37049078269 scopus 로고
    • Enantioselective bacterial biotransformation routes to cis-diol metabolites of monosubstituted benzenes, naphthalene and benzocycloalkenes of either absolute configuration
    • 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
    • (1995) J. Chem Soc. Chem. Commun. , vol.1995 , pp. 117-118
    • Allen, C.C.R.1    Boyd, D.R.2    Dalton, H.3    Sharma, N.D.4    Brannigan, I.5    Kerley, N.A.6    Sheldrake, G.N.7    Taylor, S.C.8
  • 4
    • 37049076131 scopus 로고
    • Bacterial metabolism of 6,7-dihydro-5H-benzocycloheptene by Pseudamonas putida. Synthesis and absolute configuration of benzylic alcohol and cis-diol metabolites of 6,7-dihydro-5H-benzocycloheptene
    • Boyd, D. R., M. R. J. Dorrity, J. F. Malone, R. A. S. McMordie, N. D. Sharma, H. Dalton, and P. Williams. 1990. Bacterial metabolism of 6,7-dihydro-5H-benzocycloheptene by Pseudamonas putida. Synthesis and absolute configuration of benzylic alcohol and cis-diol metabolites of 6,7-dihydro-5H-benzocycloheptene. J. Chem. Soc. Perkin Trans. I 1990:489-494.
    • (1990) J. Chem. Soc. Perkin Trans. I , vol.1990 , pp. 489-494
    • Boyd, D.R.1    Dorrity, M.R.J.2    Malone, J.F.3    McMordie, R.A.S.4    Sharma, N.D.5    Dalton, H.6    Williams, P.7
  • 5
    • 37049074697 scopus 로고
    • 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
    • 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
    • (1989) J. Chem. Soc. Chem. Commun. , vol.1989 , pp. 339-340
    • Boyd, D.R.1    McMordie, R.A.S.2    Sharma, N.D.3    Dalton, H.4    Williams, P.5    Jenkins, R.O.6
  • 6
    • 0027195608 scopus 로고
    • Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2,3-dihydrobenzofuran and benzofuran by Pseudomonas putida
    • Bojd, D. R., N. D. Sharma, R. Boyle, J. F. Malone, J. Chima, and H. Dalton. 1993. Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2,3-dihydrobenzofuran and benzofuran by Pseudomonas putida. Tetrahedron Asymmetry 4:1307-1324.
    • (1993) Tetrahedron Asymmetry , vol.4 , pp. 1307-1324
    • Bojd, D.R.1    Sharma, N.D.2    Boyle, R.3    Malone, J.F.4    Chima, J.5    Dalton, H.6
  • 7
    • 0026540763 scopus 로고
    • 1H-NMR method for the determination of enantiomeric excess and absolute configuration of cis-dihydrodiol metabolites of polycyclic arenes and heteroarenes
    • 1H-NMR method for the determination of enantiomeric excess and absolute configuration of cis-dihydrodiol metabolites of polycyclic arenes and heteroarenes Tetrahedron Lett 33:1241-1244.
    • (1992) Tetrahedron Lett , vol.33 , pp. 1241-1244
    • Boyd, D.R.1    Sharma, N.D.2    Boyle, R.3    McMordie, R.A.S.4    Chima, J.5    Dalton, H.6
  • 8
    • 0025862184 scopus 로고
    • Bacterial oxidation of benzocycloalkenes to yield monol, diol and triol metabolites
    • Boyd, D. R., N. D. Sharma, P. J. Stevenson, J. Chima, D. J. Gray, and H. Dalton. 1991 Bacterial oxidation of benzocycloalkenes to yield monol, diol and triol metabolites. Tetrahedron Lett. 32:3887-3890.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3887-3890
    • Boyd, D.R.1    Sharma, N.D.2    Stevenson, P.J.3    Chima, J.4    Gray, D.J.5    Dalton, H.6
  • 9
    • 0026787255 scopus 로고
    • Stereospecific hydroxyldtion of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1
    • Brand, J. M., D. L. Cruden, G. J. Zylstra, and D. T. Gibson. 1992 Stereospecific hydroxyldtion of indan by Escherichia coli containing the cloned toluene dioxygenase genes from Pseudomonas putida F1. Appl. Environ Microbiol 58:3407-3409
    • (1992) Appl. Environ Microbiol , vol.58 , pp. 3407-3409
    • Brand, J.M.1    Cruden, D.L.2    Zylstra, G.J.3    Gibson, D.T.4
  • 10
    • 0001345541 scopus 로고
    • The use of arene-cis-diols in synthesis
    • T. Hudlicky (ed). JAI Press, Greenwich, Conn
    • 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
    • (1993) Organic Synthesis: Theory and Applications , pp. 113-176
    • Brown, S.M.1    Hudlicky, T.2
  • 11
    • 0026659843 scopus 로고
    • The use of cyclohexa-3,5-diene-1,2-diols in enantiospecific synthesis
    • Carless, H. A. J. 1992. The use of cyclohexa-3,5-diene-1,2-diols in enantiospecific synthesis Tetrahedron Asymmetry 3:795-826.
    • (1992) Tetrahedron Asymmetry , vol.3 , pp. 795-826
    • Carless, H.A.J.1
  • 12
    • 0014969183 scopus 로고
    • Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida
    • 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.
    • (1970) Biochemistry , vol.9 , pp. 1626-1630
    • Gibson, D.T.1    Hensley, M.2    Yoshioka, H.3    Mabry, T.J.4
  • 13
    • 0029012851 scopus 로고
    • Desaturation, dioxygenation and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4
    • Gibson, D. T., S. M. Resnick, K. Lee, J. M. Brand, D. 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.
    • (1995) J. Bacteriol. , vol.177 , pp. 2615-2621
    • Gibson, D.T.1    Resnick, S.M.2    Lee, K.3    Brand, J.M.4    Torok, D.S.5    Wackett, L.P.6    Schocken, M.J.7    Haigler, B.E.8
  • 15
    • 0000757667 scopus 로고
    • Microbial degradation of aromatic hydrocarbons
    • D. T. Gibson (ed.), Marcel Dekker, Inc, New York
    • Gibson, D. T., and V. Subramaman. 1984. Microbial degradation of aromatic hydrocarbons, p. 181-251 In D. T. Gibson (ed.), Microbial degradation of organic compounds Marcel Dekker, Inc, New York.
    • (1984) Microbial Degradation of Organic Compounds , pp. 181-251
    • Gibson, D.T.1    Subramaman, V.2
  • 16
    • 0002053538 scopus 로고
    • Biotransformations catalyzed by toluene dioxygenase from Pseudomonas putida F1
    • S. Silver, A. M. Chakrabarty, B. Iglewski, and S. Kaplan (ed.), American Society for Microbiology, Washington, D.C.
    • Gibson, D. T., G. J. Zylstra, and S. Chauhan. 1990. Biotransformations catalyzed by toluene dioxygenase from Pseudomonas putida F1, p 121-132. In S. Silver, A. M. Chakrabarty, B. Iglewski, and S. Kaplan (ed.), Pseudomonas, biotransformations, pathogenesis, and evolving biotechnology. American Society for Microbiology, Washington, D.C.
    • (1990) Pseudomonas, Biotransformations, Pathogenesis, and Evolving Biotechnology , pp. 121-132
    • Gibson, D.T.1    Zylstra, G.J.2    Chauhan, S.3
  • 17
    • 0025273823 scopus 로고
    • Enzymatic oxidation of xenobiotic chemicals
    • Guengerich, F. P. 1990. Enzymatic oxidation of xenobiotic chemicals Crit. Rev. Biochem. Mol. Biol 25:97-153.
    • (1990) Crit. Rev. Biochem. Mol. Biol , vol.25 , pp. 97-153
    • Guengerich, F.P.1
  • 18
    • 0027998562 scopus 로고
    • Microbial oxidation of aromatics in enantiocontrolled synthesis 3. Design of aminocyclitols (exonitrogenous) and total synthesis of (+)-lycoricidine via acylnitrosyl cycloaddition to polarized 1-halo-1,3-cyclohexadienes
    • Hudlicky, T., H. F. Olivo, and B. McKibben. 1994. Microbial oxidation of aromatics in enantiocontrolled synthesis 3. Design of aminocyclitols (exonitrogenous) and total synthesis of (+)-lycoricidine via acylnitrosyl cycloaddition to polarized 1-halo-1,3-cyclohexadienes. J. Am. Chem. Soc 116:5108-5115.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 5108-5115
    • Hudlicky, T.1    Olivo, H.F.2    McKibben, B.3
  • 19
    • 84918255103 scopus 로고
    • Preparation of chiral allylic alcohols using Rhizopus nigricans. Use of the Haranda-Nakanishi exciton chirality method for verifying configurational assignments of allylic alcohols
    • Ito, S., M. Kasai, and H. Ziffer. 1987. Preparation of chiral allylic alcohols using Rhizopus nigricans. Use of the Haranda-Nakanishi exciton chirality method for verifying configurational assignments of allylic alcohols. Can. J. Chem. 65:574-582
    • (1987) Can. J. Chem. , vol.65 , pp. 574-582
    • Ito, S.1    Kasai, M.2    Ziffer, H.3
  • 21
    • 0012934589 scopus 로고
    • On the absolute stereochemistries of (-)-benzocyclohepten-3-ol, (-)-2,3,4,5-tetrahydro-1-benzoxepin-5-ol, and (-)-benzocycloocten-3-ol
    • Kasai, M., and H. Ziffer. 1983. On the absolute stereochemistries of (-)-benzocyclohepten-3-ol, (-)-2,3,4,5-tetrahydro-1-benzoxepin-5-ol, and (-)-benzocycloocten-3-ol. J. Org. Chem. 48:712-715
    • (1983) J. Org. Chem. , vol.48 , pp. 712-715
    • Kasai, M.1    Ziffer, H.2
  • 22
    • 5944244671 scopus 로고    scopus 로고
    • 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
    • Khan, A. A., R.-F. Wang, W.-W. Cao, W. Franklin, and C. E. Cerniglia. 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., in press.
    • Int. J. Syst. Bacteriol., in Press
    • Khan, A.A.1    Wang, R.-F.2    Cao, W.-W.3    Franklin, W.4    Cerniglia, C.E.5
  • 23
    • 0015937396 scopus 로고
    • X-ray determination of the absolute stereochemistry of the initial oxidation product formed from toluene by Pseudumonas putida 39/D
    • 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 Pseudumonas putida 39/D. J. Am. Chem. Soc 95: 4420-4421.
    • (1973) J. Am. Chem. Soc , vol.95 , pp. 4420-4421
    • Kobal, V.M.1    Gibson, D.T.2    Davis, R.E.3    Garza, A.4
  • 24
    • 0029090715 scopus 로고
    • Stereospecific sulfoxidation by toluene and naphthalene dioxygenases
    • Lee, K., J. M. Brand, and D. T. Gibson. 1995. Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem. Biophys. Res. Commun. 212:9-15.
    • (1995) Biochem. Biophys. Res. Commun. , vol.212 , pp. 9-15
    • Lee, K.1    Brand, J.M.2    Gibson, D.T.3
  • 26
    • 0024429854 scopus 로고
    • Cytochrome P-450 catalysis: Radical intermediates and dehydrogenation reactions
    • Ortiz de Montellano, P. R. 1989. Cytochrome P-450 catalysis: radical intermediates and dehydrogenation reactions. Trends Pharmacol. Sci. 10:354-359.
    • (1989) Trends Pharmacol. Sci. , vol.10 , pp. 354-359
    • Ortiz De Montellano, P.R.1
  • 27
    • 84944205754 scopus 로고
    • Synthesis of 1-hydroxy-2-(hydroxy/ hydroxymethyl)benzosuberans as potential biodynamic agents
    • Prasad, M., and S. N. Rastogi. 1984. Synthesis of 1-hydroxy-2-(hydroxy/ hydroxymethyl)benzosuberans as potential biodynamic agents. Indian J. Chem. 23B:753-757.
    • (1984) Indian J. Chem. , vol.23 B , pp. 753-757
    • Prasad, M.1    Rastogi, S.N.2
  • 28
    • 0027145644 scopus 로고
    • Biotransformation of anisole and phenetole by aerobic hydrocarbon-oxidizing bacteria
    • Resnick, S. M., and D. T. Gibson. 1993. Biotransformation of anisole and phenetole by aerobic hydrocarbon-oxidizing bacteria. Biodegradation 4:195-203
    • (1993) Biodegradation , vol.4 , pp. 195-203
    • Resnick, S.M.1    Gibson, D.T.2
  • 30
    • 0027494959 scopus 로고
    • Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase
    • Resnick, S. M., D. S. Torok, and D. T. Gibson. 1993. Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol. Lett. 113:297-302.
    • (1993) FEMS Microbiol. Lett. , vol.113 , pp. 297-302
    • Resnick, S.M.1    Torok, D.S.2    Gibson, D.T.3
  • 31
    • 0029000548 scopus 로고
    • 1H NMR determination of the absolute configuration and enantiomeric excess of bacterial and synthetic cis-diols
    • 1H NMR determination of the absolute configuration and enantiomeric excess of bacterial and synthetic cis-diols J. Org. Chem. 60:3546-3549.
    • (1995) J. Org. Chem. , vol.60 , pp. 3546-3549
    • Resnick, S.M.1    Tornk, D.S.2    Gibson, D.T.3
  • 32
    • 0028085603 scopus 로고
    • Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase
    • 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.
    • (1994) Appl Environ. Microbiol. , vol.60 , pp. 3323-3328
    • Resnick, S.M.1    Torok, D.S.2    Lee, K.3    Brand, J.M.4    Gibson, D.T.5
  • 33
    • 0002842741 scopus 로고
    • Biologically derived arene cis-dihydrodiols as synthetic building blocks
    • A. N. Collins, G. N. Sheldrake, and J. Crosby (ed.), John Wiley & Sons Ltd., Chichester, United Kingdom
    • 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.
    • (1992) Chirality in Industry: The Commercial Manufacture and Application of Optically Active Compounds , pp. 127-166
    • Sheldrake, G.N.1
  • 34
    • 0028849970 scopus 로고
    • Desaturatton and oxygenation of 1,2-dihydronaphthalene by toluene and naphthalene dioxygenase
    • Torok, D. S., S. M. Resnick, J. M. Brand, D. L. Cruden, and D. T. Gibson. 1995. Desaturatton and oxygenation of 1,2-dihydronaphthalene by toluene and naphthalene dioxygenase. J. Bacteriol. 177:5799-5805.
    • (1995) J. Bacteriol. , vol.177 , pp. 5799-5805
    • Torok, D.S.1    Resnick, S.M.2    Brand, J.M.3    Cruden, D.L.4    Gibson, D.T.5
  • 35
    • 0024295005 scopus 로고
    • Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida
    • Wackett, L. P., L. D. Kwart, and D. T. Gibson. 1988. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27:1360-1367
    • (1988) Biochemistry , vol.27 , pp. 1360-1367
    • Wackett, L.P.1    Kwart, L.D.2    Gibson, D.T.3
  • 36
    • 0000515385 scopus 로고
    • The absolute stereochemistry of several cis-dihydrodiols microbially produced from substituted benzenes
    • 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.
    • (1977) Tetrahedron , vol.33 , pp. 2491-2496
    • Ziffer, H.1    Kabuto, K.2    Gibson, D.T.3    Kobal, V.M.4    Jerina, D.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.