메뉴 건너뛰기




Volumn 64, Issue 4, 1998, Pages 1256-1263

19F nuclear magnetic resonance as a tool to investigate microbial degradation of fluorophenols to fluorocatechols and fluoromuconates

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL DERIVATIVE; MUCONIC ACID; ORGANOHALOGEN DERIVATIVE; PHENOL DERIVATIVE; DRUG DERIVATIVE; FLUORINATED HYDROCARBON; FLUORINE; SORBIC ACID;

EID: 0031594311     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.64.4.1256-1263.1998     Document Type: Article
Times cited : (47)

References (35)
  • 1
    • 0021330498 scopus 로고
    • Suicide inactivation of catechol 2,3-dioxygenase from Pseudomonas putida mt-2 by 3-halocatechols
    • Bartels, I., H.-J. Knackmuss, and W. Reineke. 1984. Suicide inactivation of catechol 2,3-dioxygenase from Pseudomonas putida mt-2 by 3-halocatechols. Appl. Environ. Microbiol. 47:500-505.
    • (1984) Appl. Environ. Microbiol. , vol.47 , pp. 500-505
    • Bartels, I.1    Knackmuss, H.-J.2    Reineke, W.3
  • 2
    • 0028784952 scopus 로고
    • From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway
    • Blasco, R., R.-M. Wittich, M. Mallavarapu, K. N. Timmis, and D. H. Pieper. 1995. From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway. J. Biol. Chem. 270:29229-29235.
    • (1995) J. Biol. Chem. , vol.270 , pp. 29229-29235
    • Blasco, R.1    Wittich, R.-M.2    Mallavarapu, M.3    Timmis, K.N.4    Pieper, D.H.5
  • 4
    • 0023224655 scopus 로고
    • Biotransformation of aromatic compounds. Monitoring fluorinated analogues by NMR
    • Cass, A. E. G., D. W. Ribbons, J. T. Rossiter, and S. R. Williams. 1987. Biotransformation of aromatic compounds. Monitoring fluorinated analogues by NMR. FEBS Lett. 220:353-357.
    • (1987) FEBS Lett. , vol.220 , pp. 353-357
    • Cass, A.E.G.1    Ribbons, D.W.2    Rossiter, J.T.3    Williams, S.R.4
  • 5
    • 0017895519 scopus 로고
    • Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol-1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad
    • Dorn, E., and H.-J. Knackmuss. 1978. Chemical structure and biodegradability of halogenated aromatic compounds. Two catechol-1,2-dioxygenases from a 3-chlorobenzoate-grown pseudomonad. Biochcm. J. 174:73-84.
    • (1978) Biochcm. J. , vol.174 , pp. 73-84
    • Dorn, E.1    Knackmuss, H.-J.2
  • 6
    • 0344852849 scopus 로고
    • Degradation of haloaromatic compounds
    • W. B. Betts (ed.). Springer-Verlag, London, United Kingdom
    • Engesser, K. H., and P. Fischer. 1991. Degradation of haloaromatic compounds, p. 15-54. In W. B. Betts (ed.), Biodegradation: natural and synthetic materials. Springer-Verlag, London, United Kingdom.
    • (1991) Biodegradation: Natural and Synthetic Materials , pp. 15-54
    • Engesser, K.H.1    Fischer, P.2
  • 7
    • 0015053131 scopus 로고
    • Bacterial metabolism of 4-chlorophenoxyacetate
    • Evans, W. C., B. S. W. Smith, P. Moss, and H. N. Fernley. 1971. Bacterial metabolism of 4-chlorophenoxyacetate. Biochem. J. 122:509-517.
    • (1971) Biochem. J. , vol.122 , pp. 509-517
    • Evans, W.C.1    Smith, B.S.W.2    Moss, P.3    Fernley, H.N.4
  • 8
    • 0018341179 scopus 로고
    • Metabolism of phenol and resorcinol in Trichosporon cutaneum
    • Gaal, A., and H. Y. Neujahr. 1979. Metabolism of phenol and resorcinol in Trichosporon cutaneum. J. Bacteriol. 137:13-21.
    • (1979) J. Bacteriol. , vol.137 , pp. 13-21
    • Gaal, A.1    Neujahr, H.Y.2
  • 11
    • 84989085045 scopus 로고
    • 19F couplings using the heteronuclear equivalent of the COSY experiment
    • 19F couplings using the heteronuclear equivalent of the COSY experiment. Magn. Reson. Chem. 29:387-397.
    • (1991) Magn. Reson. Chem. , vol.29 , pp. 387-397
    • Hughes, D.W.1    Bain, A.D.2
  • 12
    • 0021058897 scopus 로고
    • Monochlorophenols as substrates of the enzymes of preparatory phenol metabolism in the yeast Candida tropicalis
    • Ivoilov, V. S., and Y. N. Karasevich. 1983. Monochlorophenols as substrates of the enzymes of preparatory phenol metabolism in the yeast Candida tropicalis. Mikrobiologiya 52:956-961.
    • (1983) Mikrobiologiya , vol.52 , pp. 956-961
    • Ivoilov, V.S.1    Karasevich, Y.N.2
  • 13
    • 0028857637 scopus 로고
    • Maleylacetate reductase of Pseudomonas sp. strain B13: Specificity of substrate conversion and halide elimination
    • Kaschabek, S. R., and W. Reineke. 1995. Maleylacetate reductase of Pseudomonas sp. strain B13: specificity of substrate conversion and halide elimination. J. Bacteriol. 177:320-325.
    • (1995) J. Bacteriol. , vol.177 , pp. 320-325
    • Kaschabek, S.R.1    Reineke, W.2
  • 14
    • 0022962816 scopus 로고
    • Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. Some properties of the first two enzymes of the degradation pathway
    • Krug, M., and G. Straube. 1986. Degradation of phenolic compounds by the yeast Candida tropicalis HP 15. Some properties of the first two enzymes of the degradation pathway. J. Basic Microbiol. 26:271-281.
    • (1986) J. Basic Microbiol. , vol.26 , pp. 271-281
    • Krug, M.1    Straube, G.2
  • 15
    • 0024353044 scopus 로고
    • The application of nuclear magnetic resonance spectroscopy to drug metabolism studies
    • Malet-Martino, M. C., and R. Martino. 1989. The application of nuclear magnetic resonance spectroscopy to drug metabolism studies. Xenobiotica 19:583-607.
    • (1989) Xenobiotica , vol.19 , pp. 583-607
    • Malet-Martino, M.C.1    Martino, R.2
  • 16
    • 0028224548 scopus 로고
    • Cis,cis-muconate lactonizing enzyme from Trichosporon cutaneum: Evidence for a novel class of cycloisomerases in eucaryotes
    • Mazur, P., W. A. Pieken, S. R. Budihas, S. E. Williams, S. Wong, and J. W. Kozarich. 1994. Cis,cis-muconate lactonizing enzyme from Trichosporon cutaneum: evidence for a novel class of cycloisomerases in eucaryotes. Biochemistry 33:1961-1970.
    • (1994) Biochemistry , vol.33 , pp. 1961-1970
    • Mazur, P.1    Pieken, W.A.2    Budihas, S.R.3    Williams, S.E.4    Wong, S.5    Kozarich, J.W.6
  • 17
    • 0027327211 scopus 로고
    • Catabolism of benzene compounds by ascomycetous and basidiomycetous yeasts and yeastlike fungi. A literature review and an experimental approach
    • Middelhoven, W. J. 1993. Catabolism of benzene compounds by ascomycetous and basidiomycetous yeasts and yeastlike fungi. A literature review and an experimental approach. Antonie Leeuwenhoek 63:125-144.
    • (1993) Antonie Leeuwenhoek , vol.63 , pp. 125-144
    • Middelhoven, W.J.1
  • 18
    • 0024258298 scopus 로고
    • Purification and properties of catechol 1,2-dioxygenase (pyrocatechase) from Pseudomonas putida mt-2 in comparison with that from Pseudomonas arvilla C-1
    • Nakai, C., T. Nakazawa, and M. Nozaki. 1988. Purification and properties of catechol 1,2-dioxygenase (pyrocatechase) from Pseudomonas putida mt-2 in comparison with that from Pseudomonas arvilla C-1. Arch. Biochem. Biophys. 267:701-713.
    • (1988) Arch. Biochem. Biophys. , vol.267 , pp. 701-713
    • Nakai, C.1    Nakazawa, T.2    Nozaki, M.3
  • 19
    • 0028838117 scopus 로고
    • Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics
    • Peelen, S., I. M. C. M. Rietjens, M. G. Boersma, and J. Vervoort. 1995. Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. A comparison of regioselectivity and rate of conversion with calculated molecular orbital substrate characteristics. Eur. J. Biochem. 227:284-291.
    • (1995) Eur. J. Biochem. , vol.227 , pp. 284-291
    • Peelen, S.1    Rietjens, I.M.C.M.2    Boersma, M.G.3    Vervoort, J.4
  • 20
    • 0021329184 scopus 로고
    • Microbial metabolism of haloaromatics: Isolation and properties of a chlorobenzene-degrading bacterium
    • Reineke, W., and H.-J. Knackmuss. 1984. Microbial metabolism of haloaromatics: isolation and properties of a chlorobenzene-degrading bacterium. Appl. Environ. Microbiol. 47:395-402.
    • (1984) Appl. Environ. Microbiol. , vol.47 , pp. 395-402
    • Reineke, W.1    Knackmuss, H.-J.2
  • 21
  • 23
    • 0025164680 scopus 로고
    • Enzymatic formation, stability, and spontaneous reactions of 4-fluoromuconolactone, a metabolite of the bacterial degradation of 4-fluorobenzoate
    • Schlömann, M., P. Fischer, E. Schmidt, and H.-J. Knackmuss. 1990. Enzymatic formation, stability, and spontaneous reactions of 4-fluoromuconolactone, a metabolite of the bacterial degradation of 4-fluorobenzoate. J. Bacteriol. 172:5119-5129.
    • (1990) J. Bacteriol. , vol.172 , pp. 5119-5129
    • Schlömann, M.1    Fischer, P.2    Schmidt, E.3    Knackmuss, H.-J.4
  • 24
    • 0019162442 scopus 로고
    • Chemical structure and biodegradability of halogenated aromatic compounds
    • Schmidt, E., and H.-J. Knackmuss. 1980. Chemical structure and biodegradability of halogenated aromatic compounds. Biochem. J. 192:339-347.
    • (1980) Biochem. J. , vol.192 , pp. 339-347
    • Schmidt, E.1    Knackmuss, H.-J.2
  • 25
    • 0027522089 scopus 로고
    • Purification and characterization of maleylacetate reductase from Alcaligenes eutrophus JMP134(pJP4)
    • Seibert, V., K. Stadler-Fritzsche, and M. Schlömann. 1993. Purification and characterization of maleylacetate reductase from Alcaligenes eutrophus JMP134(pJP4). J. Bacteriol. 175:6745-6754.
    • (1993) J. Bacteriol. , vol.175 , pp. 6745-6754
    • Seibert, V.1    Stadler-Fritzsche, K.2    Schlömann, M.3
  • 26
    • 0029014004 scopus 로고
    • Characterization of muconate and chloromuconate cycloisomerase from Rhodococcus erythropolis 1CP: Indications for functionally convergent evolution among bacterial cycloisomerases
    • Solyanikova, I. P., O. V. Maltseva, M. D. Vollmer, L. A. Golovleva, and M. Schlömann. 1995. Characterization of muconate and chloromuconate cycloisomerase from Rhodococcus erythropolis 1CP: indications for functionally convergent evolution among bacterial cycloisomerases. J. Bacteriol. 177: 2821-2826.
    • (1995) J. Bacteriol. , vol.177 , pp. 2821-2826
    • Solyanikova, I.P.1    Maltseva, O.V.2    Vollmer, M.D.3    Golovleva, L.A.4    Schlömann, M.5
  • 27
    • 84985058010 scopus 로고
    • Die Stereochemie der fragmentierenden Enthalogenierung von 1-Chlor-1-fluor-2-(1-halogenalkyl)cyclopropanan
    • Spahic, B., and M. Schlosser. 1980. Die Stereochemie der fragmentierenden Enthalogenierung von 1-Chlor-1-fluor-2-(1-halogenalkyl)cyclopropanan. Helv. Chim. Acta 63:1242-1256.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 1242-1256
    • Spahic, B.1    Schlosser, M.2
  • 28
    • 0023240899 scopus 로고
    • Degradation of 1,4-dichlorobenzene by a Pseudomonas sp
    • Spain, J. C., and S. F. Nishino. 1987. Degradation of 1,4-dichlorobenzene by a Pseudomonas sp. Appl. Environ. Microbiol. 53:1010-1019.
    • (1987) Appl. Environ. Microbiol. , vol.53 , pp. 1010-1019
    • Spain, J.C.1    Nishino, S.F.2
  • 30
    • 0027411511 scopus 로고
    • Conversion of 2-chloromaleylacetate in Alcaligenes eutrophus JMP134
    • Vollmer, M. D., K. Stadler-Fritzsche, and M. Schlömann. 1993. Conversion of 2-chloromaleylacetate in Alcaligenes eutrophus JMP134. Arch. Microbiol. 159:182-188.
    • (1993) Arch. Microbiol. , vol.159 , pp. 182-188
    • Vollmer, M.D.1    Stadler-Fritzsche, K.2    Schlömann, M.3
  • 31
    • 0028364164 scopus 로고
    • Inability of muconate cycloisomerases to cause dehalogenation during conversion of 2-chloro-cis,cis-muconate
    • Vollmer, M. D., P. Fischer, H.-J. Knackmuss, and M. Schlömann. 1994. Inability of muconate cycloisomerases to cause dehalogenation during conversion of 2-chloro-cis,cis-muconate. J. Bacteriol. 176:4366-4375.
    • (1994) J. Bacteriol. , vol.176 , pp. 4366-4375
    • Vollmer, M.D.1    Fischer, P.2    Knackmuss, H.-J.3    Schlömann, M.4
  • 32
    • 0029077739 scopus 로고
    • Conversion of 2-chloro-cis,cis-muconate and its metabolites 2-chloro- And 5-chloromuconolactone by chloromuconate cycloisomerases of pJP4 and pAC27
    • Vollmer, M. D., and M. Schlömann. 1995. Conversion of 2-chloro-cis,cis-muconate and its metabolites 2-chloro-and 5-chloromuconolactone by chloromuconate cycloisomerases of pJP4 and pAC27. J. Bacteriol. 177:2938-2941.
    • (1995) J. Bacteriol. , vol.177 , pp. 2938-2941
    • Vollmer, M.D.1    Schlömann, M.2
  • 33
    • 0021100402 scopus 로고
    • Halogenated protocatechuates as substrates for protocatechuate dioxygenase from Pseudomonas cepacia
    • Walsh, T. A., and D. P. Ballou. 1983. Halogenated protocatechuates as substrates for protocatechuate dioxygenase from Pseudomonas cepacia. J. Biol. Chem. 258:14413-14421.
    • (1983) J. Biol. Chem. , vol.258 , pp. 14413-14421
    • Walsh, T.A.1    Ballou, D.P.2
  • 34
    • 0021100507 scopus 로고
    • Rapid reaction studies on the oxygenation reactions of catechol dioxygenase
    • Walsh, T. A., D. P. Ballou, R. Mayer, and L. Que, Jr. 1983. Rapid reaction studies on the oxygenation reactions of catechol dioxygenase. J. Biol. Chem. 258:14422-14427.
    • (1983) J. Biol. Chem. , vol.258 , pp. 14422-14427
    • Walsh, T.A.1    Ballou, D.P.2    Mayer, R.3    Que L., Jr.4
  • 35
    • 0342720828 scopus 로고
    • Fluorine-19 nuclear magnetic resonance spectroscopy
    • Wray, V. 1983. Fluorine-19 nuclear magnetic resonance spectroscopy. Annu. Rep. NMR Spectrosc. 14:179-191.
    • (1983) Annu. Rep. NMR Spectrosc. , vol.14 , pp. 179-191
    • Wray, V.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.