메뉴 건너뛰기




Volumn 192, Issue 3, 2011, Pages 1633-1640

Enantioselective degradation and unidirectional chiral inversion of 2-phenylbutyric acid, an intermediate from linear alkylbenzene, by Xanthobacter flavus PA1

Author keywords

2 Phenylbutyric acid; Chiral inversion; Enantioselective biodegradation; Linear alkylbenzene sulfonates; Xanthobacter flavus

Indexed keywords

BACTERIA; ENANTIOMERS; ENANTIOSELECTIVITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 80052032514     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2011.06.088     Document Type: Article
Times cited : (5)

References (50)
  • 1
    • 33749016750 scopus 로고    scopus 로고
    • Environmental fate processes and biochemical transformations of chiral emerging organic pollutants
    • Wong C.S. Environmental fate processes and biochemical transformations of chiral emerging organic pollutants. Anal. Bioanal. Chem. 2006, 386:544-558.
    • (2006) Anal. Bioanal. Chem. , vol.386 , pp. 544-558
    • Wong, C.S.1
  • 2
    • 14144251068 scopus 로고    scopus 로고
    • Enantioselectivity in environmental safety of current chiral insecticides
    • Liu W., Gan J., Schlenk D., Jury W.A. Enantioselectivity in environmental safety of current chiral insecticides. Proc. Natl. Acad. Sci. 2005, 102:701-706.
    • (2005) Proc. Natl. Acad. Sci. , vol.102 , pp. 701-706
    • Liu, W.1    Gan, J.2    Schlenk, D.3    Jury, W.A.4
  • 3
    • 2442419885 scopus 로고    scopus 로고
    • Chirality of pollutants-effects on metabolism and fate
    • Müller T.A., Kohler H.-P.E. Chirality of pollutants-effects on metabolism and fate. Appl. Microbiol. Biotechnol. 2004, 64:300-316.
    • (2004) Appl. Microbiol. Biotechnol. , vol.64 , pp. 300-316
    • Müller, T.A.1    Kohler, H.-P.E.2
  • 4
    • 65449158134 scopus 로고    scopus 로고
    • Enantioselective estrogenicity of o,p'-dichlorodiphenyltrichloroethane in the MCF-7 human breast carcinoma cell line
    • Wang L., Zhou S., Lin K., Zhao M., Liu W., Gan J. Enantioselective estrogenicity of o,p'-dichlorodiphenyltrichloroethane in the MCF-7 human breast carcinoma cell line. Environ. Toxicol. Chem. 2009, 28:1-8.
    • (2009) Environ. Toxicol. Chem. , vol.28 , pp. 1-8
    • Wang, L.1    Zhou, S.2    Lin, K.3    Zhao, M.4    Liu, W.5    Gan, J.6
  • 5
    • 33746578492 scopus 로고    scopus 로고
    • Enantioselective degradation and chiral stability of pyrethroids in soil and sediment
    • Qin S., Budd R., Bondarenko S., Liu W., Gan J. Enantioselective degradation and chiral stability of pyrethroids in soil and sediment. J. Agric. Food Chem. 2006, 54:5040-5045.
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 5040-5045
    • Qin, S.1    Budd, R.2    Bondarenko, S.3    Liu, W.4    Gan, J.5
  • 6
    • 1642395893 scopus 로고    scopus 로고
    • Evidence of enantioselective degradation of α-hexachlorocyclohexane in groundwater
    • Law S.A., Bidleman T.F., Martin M.J., Ruby M.V. Evidence of enantioselective degradation of α-hexachlorocyclohexane in groundwater. Environ. Sci. Technol. 2004, 38:1633-1638.
    • (2004) Environ. Sci. Technol. , vol.38 , pp. 1633-1638
    • Law, S.A.1    Bidleman, T.F.2    Martin, M.J.3    Ruby, M.V.4
  • 7
    • 0037080148 scopus 로고    scopus 로고
    • Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil
    • Buser H.-R., Müller M.D., Poiger T., Balmer M.E. Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil. Environ. Sci. Technol. 2002, 36:221-226.
    • (2002) Environ. Sci. Technol. , vol.36 , pp. 221-226
    • Buser, H.-R.1    Müller, M.D.2    Poiger, T.3    Balmer, M.E.4
  • 9
    • 0032815759 scopus 로고    scopus 로고
    • Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge
    • Zipper C., Fleischmann T., Kohler H.-P.E. Aerobic biodegradation of chiral phenoxyalkanoic acid derivatives during incubations with activated sludge. FEMS Microbiol. Ecol. 1999, 29:197-204.
    • (1999) FEMS Microbiol. Ecol. , vol.29 , pp. 197-204
    • Zipper, C.1    Fleischmann, T.2    Kohler, H.-P.E.3
  • 10
    • 77952552212 scopus 로고    scopus 로고
    • Faster degradation of herbicidally-active enantiomer of imidazolinones in soils
    • Ramezani M.K., Oliver D.P., Kookana R.S., Lao W., Gill G., Preston C. Faster degradation of herbicidally-active enantiomer of imidazolinones in soils. Chemosphere 2010, 79:1040-1045.
    • (2010) Chemosphere , vol.79 , pp. 1040-1045
    • Ramezani, M.K.1    Oliver, D.P.2    Kookana, R.S.3    Lao, W.4    Gill, G.5    Preston, C.6
  • 11
    • 0028132696 scopus 로고
    • Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid] by mixed and pure bacterial cultures
    • Tett V.A., Willetts A.J., Lappin-Scott H.M. Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid] by mixed and pure bacterial cultures. FEMS Microbiol. Ecol. 1994, 14:191-199.
    • (1994) FEMS Microbiol. Ecol. , vol.14 , pp. 191-199
    • Tett, V.A.1    Willetts, A.J.2    Lappin-Scott, H.M.3
  • 12
    • 0030793688 scopus 로고    scopus 로고
    • Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans
    • Tett V.A., Willetts A.J., Lappin-Scott H.M. Biodegradation of the chlorophenoxy herbicide (R)-(+)-mecoprop by Alcaligenes denitrificans. Biodegradation 1997, 8:43-52.
    • (1997) Biodegradation , vol.8 , pp. 43-52
    • Tett, V.A.1    Willetts, A.J.2    Lappin-Scott, H.M.3
  • 13
    • 0031802163 scopus 로고    scopus 로고
    • Enantioselective uptake and degradation of the chiral herbicide dichlorprop [(RS)-2-(2,4-dichlorophenoxy)propanoic acid] by Sphingomonas herbicidovorans MH
    • Zipper C., Bunk M., Zehnder A.J.B., Kohler H.-P.E. Enantioselective uptake and degradation of the chiral herbicide dichlorprop [(RS)-2-(2,4-dichlorophenoxy)propanoic acid] by Sphingomonas herbicidovorans MH. J. Bacteriol. 1998, 180:3368-3374.
    • (1998) J. Bacteriol. , vol.180 , pp. 3368-3374
    • Zipper, C.1    Bunk, M.2    Zehnder, A.J.B.3    Kohler, H.-P.E.4
  • 14
    • 0029979765 scopus 로고    scopus 로고
    • Complete microbial degradation of both enantiomers of the chiral herbicide mecoprop [(RS)-2-(4-chloro-2-methylphenoxy)propionic acid] in an enantioselective manner by Sphingomonas herbicidovorans sp. nov
    • Zipper C., Nickel K., Angst W., Kohler H.-P.E. Complete microbial degradation of both enantiomers of the chiral herbicide mecoprop [(RS)-2-(4-chloro-2-methylphenoxy)propionic acid] in an enantioselective manner by Sphingomonas herbicidovorans sp. nov. Appl. Environ. Microbiol. 1996, 62:4318-4322.
    • (1996) Appl. Environ. Microbiol. , vol.62 , pp. 4318-4322
    • Zipper, C.1    Nickel, K.2    Angst, W.3    Kohler, H.-P.E.4
  • 15
    • 33644961210 scopus 로고    scopus 로고
    • Preferential attack of the (S)-configured ether-linked carbons in bis-(1-chloro-2-propyl) ether by Rhodococcus sp. strain DTB
    • Garbe L.-A., Moreno-Horn M., Tressl R., Görisch H. Preferential attack of the (S)-configured ether-linked carbons in bis-(1-chloro-2-propyl) ether by Rhodococcus sp. strain DTB. FEMS Microbiol. Ecol. 2006, 55:113-121.
    • (2006) FEMS Microbiol. Ecol. , vol.55 , pp. 113-121
    • Garbe, L.-A.1    Moreno-Horn, M.2    Tressl, R.3    Görisch, H.4
  • 16
    • 33746055712 scopus 로고    scopus 로고
    • Purification and characterization of two enantioselective α-ketoglutarate-dependent dioxygenases, RdpA and SdpA, from Sphingomonas herbicidovorans MH
    • Müller T.A., Fleischmann T., van der Meer J.R., Kohler H.-P.E. Purification and characterization of two enantioselective α-ketoglutarate-dependent dioxygenases, RdpA and SdpA, from Sphingomonas herbicidovorans MH. Appl. Environ. Microbiol. 2006, 72:4853-4861.
    • (2006) Appl. Environ. Microbiol. , vol.72 , pp. 4853-4861
    • Müller, T.A.1    Fleischmann, T.2    van der Meer, J.R.3    Kohler, H.-P.E.4
  • 17
    • 4644224875 scopus 로고    scopus 로고
    • Localization and characterization of two novel genes encoding stereospecific dioxygenases catalyzing 2(2,4-dichlorophenoxy)propionate cleavage in Delftia acidovorans MC1
    • Schleinitz K.M., Kleinsteuber S., Vallaeys T., Babel W. Localization and characterization of two novel genes encoding stereospecific dioxygenases catalyzing 2(2,4-dichlorophenoxy)propionate cleavage in Delftia acidovorans MC1. Appl. Environ. Microbiol. 2004, 70:5357-5365.
    • (2004) Appl. Environ. Microbiol. , vol.70 , pp. 5357-5365
    • Schleinitz, K.M.1    Kleinsteuber, S.2    Vallaeys, T.3    Babel, W.4
  • 19
    • 0030708622 scopus 로고    scopus 로고
    • Involvement of two alpha-ketoglutarate-dependent dioxygenases in enantioselective degradation of (R)- and (S)-mecoprop by Sphingomonas herbicidovorans MH
    • Nickel K., Suter M.J.-F., Kohler H.-P.E. Involvement of two alpha-ketoglutarate-dependent dioxygenases in enantioselective degradation of (R)- and (S)-mecoprop by Sphingomonas herbicidovorans MH. J. Bacteriol. 1997, 179:6674-6679.
    • (1997) J. Bacteriol. , vol.179 , pp. 6674-6679
    • Nickel, K.1    Suter, M.J.-F.2    Kohler, H.-P.E.3
  • 20
    • 0038220923 scopus 로고    scopus 로고
    • Purification and characterization of an inverting stereo- and enantioselective sec-alkylsulfatase from the gram-positive bacterium Rhodococcus ruber DSM 44541
    • Pogorevc M., Faber K. Purification and characterization of an inverting stereo- and enantioselective sec-alkylsulfatase from the gram-positive bacterium Rhodococcus ruber DSM 44541. Appl. Environ. Microbiol. 2003, 69:2810-2815.
    • (2003) Appl. Environ. Microbiol. , vol.69 , pp. 2810-2815
    • Pogorevc, M.1    Faber, K.2
  • 21
    • 0037954172 scopus 로고    scopus 로고
    • Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 1. Enantiomerization and enantioselective degradation of the chiral 2-phenoxypropionic acid herbicides
    • Müller M.D., Buser H.-R. Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 1. Enantiomerization and enantioselective degradation of the chiral 2-phenoxypropionic acid herbicides. Environ. Sci. Technol. 1997, 31:1953-1959.
    • (1997) Environ. Sci. Technol. , vol.31 , pp. 1953-1959
    • Müller, M.D.1    Buser, H.-R.2
  • 22
    • 0343329895 scopus 로고    scopus 로고
    • Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 2. Elucidation of the enantiomerization process of chiral phenoxy acids from incubation in a D2O/soil system
    • Buser H.-R., Müller M.D. Conversion reactions of various phenoxyalkanoic acid herbicides in soil. 2. Elucidation of the enantiomerization process of chiral phenoxy acids from incubation in a D2O/soil system. Environ. Sci. Technol. 1997, 31:1960-1967.
    • (1997) Environ. Sci. Technol. , vol.31 , pp. 1960-1967
    • Buser, H.-R.1    Müller, M.D.2
  • 23
    • 2642697831 scopus 로고    scopus 로고
    • Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland
    • Buser H.-R., Müller M.D. Occurrence and transformation reactions of chiral and achiral phenoxyalkanoic acid herbicides in lakes and rivers in Switzerland. Environ. Sci. Technol. 1998, 32:626-633.
    • (1998) Environ. Sci. Technol. , vol.32 , pp. 626-633
    • Buser, H.-R.1    Müller, M.D.2
  • 24
    • 0036782116 scopus 로고    scopus 로고
    • Putting chirality to work: the strategy of chiral switches
    • Agranat I., Caner H., Caldwell J. Putting chirality to work: the strategy of chiral switches. Nat. Rev. Drug Discov. 2002, 1:753-768.
    • (2002) Nat. Rev. Drug Discov. , vol.1 , pp. 753-768
    • Agranat, I.1    Caner, H.2    Caldwell, J.3
  • 25
    • 0035986506 scopus 로고    scopus 로고
    • The behavior of polar aromatic sulfonates during drinking water production: a case study on sulfophenyl carboxylates in two European waterworks
    • Eichhorn P., Knepper T.P., Ventura F., Diaz A. The behavior of polar aromatic sulfonates during drinking water production: a case study on sulfophenyl carboxylates in two European waterworks. Water Res. 2002, 36:2179-2186.
    • (2002) Water Res. , vol.36 , pp. 2179-2186
    • Eichhorn, P.1    Knepper, T.P.2    Ventura, F.3    Diaz, A.4
  • 26
    • 11144354588 scopus 로고    scopus 로고
    • Biodegradation of linear alkylbenzene sulfonates and their degradation intermediates in seawater
    • León V.M., Gómez-Parra A., González-Mazo E. Biodegradation of linear alkylbenzene sulfonates and their degradation intermediates in seawater. Environ. Sci. Technol. 2004, 38:2359-2367.
    • (2004) Environ. Sci. Technol. , vol.38 , pp. 2359-2367
    • León, V.M.1    Gómez-Parra, A.2    González-Mazo, E.3
  • 27
    • 0343658521 scopus 로고    scopus 로고
    • Monitoring long-chain intermediate products from the degradation of linear alkylbenzene sulfonates in the marine environment by solid-phase extraction followed by liquid chromatography/ionspray mass spectrometry
    • González-Mazo E., Honing M., Barceló D., Gómez-Parra A. Monitoring long-chain intermediate products from the degradation of linear alkylbenzene sulfonates in the marine environment by solid-phase extraction followed by liquid chromatography/ionspray mass spectrometry. Environ. Sci. Technol. 1997, 31:504-510.
    • (1997) Environ. Sci. Technol. , vol.31 , pp. 504-510
    • González-Mazo, E.1    Honing, M.2    Barceló, D.3    Gómez-Parra, A.4
  • 29
    • 0343603525 scopus 로고    scopus 로고
    • Handling of marine and estuarine samples for the determination of linear alkylbenzene sulfonates and sulfophenylcarboxylic acids
    • León V.M., González-Mazo E., Gómez-Parra A. Handling of marine and estuarine samples for the determination of linear alkylbenzene sulfonates and sulfophenylcarboxylic acids. J. Chromatogr. A 2000, 889:211-219.
    • (2000) J. Chromatogr. A , vol.889 , pp. 211-219
    • León, V.M.1    González-Mazo, E.2    Gómez-Parra, A.3
  • 31
    • 0034059439 scopus 로고    scopus 로고
    • An α-proteobacterium converts linear alkylbenzenesulfonate surfactants into sulfophenylcarboxylates and linear alkyldiphenyletherdisulfonate surfactants into sulfodiphenylethercarboxylates
    • Schleheck D., Dong W., Denger K., Heinzle E., Cook A.M. An α-proteobacterium converts linear alkylbenzenesulfonate surfactants into sulfophenylcarboxylates and linear alkyldiphenyletherdisulfonate surfactants into sulfodiphenylethercarboxylates. Appl. Environ. Microbiol. 2000, 66:1911-1916.
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 1911-1916
    • Schleheck, D.1    Dong, W.2    Denger, K.3    Heinzle, E.4    Cook, A.M.5
  • 32
    • 34250851829 scopus 로고    scopus 로고
    • Monitoring the primary biodegradation of linear alkylbenzene sulfonates and their coproducts in anoxic sediments using liquid chromatography-mass spectrometry
    • Lara-Martin P.A., Gomez-Parra A., Kochling T., Sanz J.L., Gonzalez-Mazo E. Monitoring the primary biodegradation of linear alkylbenzene sulfonates and their coproducts in anoxic sediments using liquid chromatography-mass spectrometry. Environ. Sci. Technol. 2007, 41:3580-3586.
    • (2007) Environ. Sci. Technol. , vol.41 , pp. 3580-3586
    • Lara-Martin, P.A.1    Gomez-Parra, A.2    Kochling, T.3    Sanz, J.L.4    Gonzalez-Mazo, E.5
  • 33
    • 3242753673 scopus 로고    scopus 로고
    • Mineralization of individual congeners of linear alkylbenzenesulfonate by defined pairs of heterotrophic bacteria
    • Schleheck D., Knepper T.P., Fischer K., Cook A.M. Mineralization of individual congeners of linear alkylbenzenesulfonate by defined pairs of heterotrophic bacteria. Appl. Environ. Microbiol. 2004, 70:4053-4063.
    • (2004) Appl. Environ. Microbiol. , vol.70 , pp. 4053-4063
    • Schleheck, D.1    Knepper, T.P.2    Fischer, K.3    Cook, A.M.4
  • 34
    • 0026615648 scopus 로고
    • Complete oxidation of linear alkylbenzene sulfonate by bacterial communities selected from coastal seawater
    • Sigoillot J.-C., Nguyen M.-H. Complete oxidation of linear alkylbenzene sulfonate by bacterial communities selected from coastal seawater. Appl. Environ. Microbiol. 1992, 58:1308-1312.
    • (1992) Appl. Environ. Microbiol. , vol.58 , pp. 1308-1312
    • Sigoillot, J.-C.1    Nguyen, M.-H.2
  • 35
    • 76149107167 scopus 로고    scopus 로고
    • The missing link in linear alkylbenzenesulfonate surfactant degradation: 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl)butyrate by Comamonas testosteroni KF-1
    • Schleheck D., von Netzer F., Fleischmann T., Rentsch D., Huhn T., Cook A.M., Kohler H.P. The missing link in linear alkylbenzenesulfonate surfactant degradation: 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl)butyrate by Comamonas testosteroni KF-1. Appl. Environ. Microbiol. 2010, 76:196-202.
    • (2010) Appl. Environ. Microbiol. , vol.76 , pp. 196-202
    • Schleheck, D.1    von Netzer, F.2    Fleischmann, T.3    Rentsch, D.4    Huhn, T.5    Cook, A.M.6    Kohler, H.P.7
  • 36
    • 77749258519 scopus 로고    scopus 로고
    • Anaerobic degradation pathway of linear alkylbenzene sulfonates (LAS) in sulfate-reducing marine sediments
    • Lara-Martin P.A., Gomez-Parra A., Sanz J.L., Gonzalez-Mazo E. Anaerobic degradation pathway of linear alkylbenzene sulfonates (LAS) in sulfate-reducing marine sediments. Environ. Sci. Technol. 2010, 44:1670-1676.
    • (2010) Environ. Sci. Technol. , vol.44 , pp. 1670-1676
    • Lara-Martin, P.A.1    Gomez-Parra, A.2    Sanz, J.L.3    Gonzalez-Mazo, E.4
  • 37
    • 77950340502 scopus 로고    scopus 로고
    • Anaerobic degradation of linear alkylbenzene sulfonate (LAS) in fluidized bed reactor by microbial consortia in different support materials
    • de Oliveira L.L., Costa R.B., Okada D.Y., Vich D.V., Duarte I.C., Silva E.L., Varesche M.B. Anaerobic degradation of linear alkylbenzene sulfonate (LAS) in fluidized bed reactor by microbial consortia in different support materials. Bioresource Technol. 2010, 101:5112-5122.
    • (2010) Bioresource Technol. , vol.101 , pp. 5112-5122
    • de Oliveira, L.L.1    Costa, R.B.2    Okada, D.Y.3    Vich, D.V.4    Duarte, I.C.5    Silva, E.L.6    Varesche, M.B.7
  • 38
    • 0020394743 scopus 로고
    • Degradation of 3-phenylbutyric acid by Pseudomonas sp.
    • Sariaslani F.S., Sudmeier J.L., Focht D.D. Degradation of 3-phenylbutyric acid by Pseudomonas sp. J. Bacteriol. 1982, 152:411-421.
    • (1982) J. Bacteriol. , vol.152 , pp. 411-421
    • Sariaslani, F.S.1    Sudmeier, J.L.2    Focht, D.D.3
  • 39
    • 0029911753 scopus 로고    scopus 로고
    • Enantioselective metabolism of chiral 3-phenylbutyric acid, an intermediate of linear alkylbenzene degradation, by Rhodococcus rhodochrous PB1
    • Simoni S., Klinke S., Zipper C., Angst W., Kohler H.-P.E. Enantioselective metabolism of chiral 3-phenylbutyric acid, an intermediate of linear alkylbenzene degradation, by Rhodococcus rhodochrous PB1. Appl. Environ. Microbiol. 1996, 62:749-755.
    • (1996) Appl. Environ. Microbiol. , vol.62 , pp. 749-755
    • Simoni, S.1    Klinke, S.2    Zipper, C.3    Angst, W.4    Kohler, H.-P.E.5
  • 40
    • 0034095435 scopus 로고    scopus 로고
    • Enantiomeric degradation of 2-(4-sulfophenyl)butyrate via 4-sulfocatechol in Delftia acidovorans SPB1
    • Schulz S., Dong W., Groth U., Cook A.M. Enantiomeric degradation of 2-(4-sulfophenyl)butyrate via 4-sulfocatechol in Delftia acidovorans SPB1. Appl. Environ. Microbiol. 2000, 66:1905-1910.
    • (2000) Appl. Environ. Microbiol. , vol.66 , pp. 1905-1910
    • Schulz, S.1    Dong, W.2    Groth, U.3    Cook, A.M.4
  • 41
    • 0036005636 scopus 로고    scopus 로고
    • Understanding nature's strategies for enzyme-catalyzed racemization and epimerization
    • Tanner M.E. Understanding nature's strategies for enzyme-catalyzed racemization and epimerization. Acc. Chem. Res. 2002, 35:237-246.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 237-246
    • Tanner, M.E.1
  • 42
  • 43
    • 33947722903 scopus 로고    scopus 로고
    • A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery
    • Reddy A., Hashim M., Wang Z., Penn L., Stankovic C.J., Burdette D., Surendran N., Cai H. A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery. Int. J. Pharm. 2007, 335:63-69.
    • (2007) Int. J. Pharm. , vol.335 , pp. 63-69
    • Reddy, A.1    Hashim, M.2    Wang, Z.3    Penn, L.4    Stankovic, C.J.5    Burdette, D.6    Surendran, N.7    Cai, H.8
  • 46
    • 0027471547 scopus 로고
    • Metabolic inversion of (R)-ibuprofen. Formation of ibuprofenyl-coenzyme A
    • Tracy T.S., Wirthwein D.P., Hall S.D. Metabolic inversion of (R)-ibuprofen. Formation of ibuprofenyl-coenzyme A. Drug Metab. Dispos. 1993, 21:114-120.
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 114-120
    • Tracy, T.S.1    Wirthwein, D.P.2    Hall, S.D.3
  • 47
    • 0027440325 scopus 로고
    • Modulation of enantioselective metabolism and inversion of ibuprofen by xenobiotics in isolated rat hepatocytes
    • Xiaotao Q., Hall S.D. Modulation of enantioselective metabolism and inversion of ibuprofen by xenobiotics in isolated rat hepatocytes. J. Pharmacol. Exp. Ther. 1993, 266:845-851.
    • (1993) J. Pharmacol. Exp. Ther. , vol.266 , pp. 845-851
    • Xiaotao, Q.1    Hall, S.D.2
  • 48
    • 0030903324 scopus 로고    scopus 로고
    • Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen
    • Reichel C., Brugger R., Bang H., Geisslinger G., Brune K. Molecular cloning and expression of a 2-arylpropionyl-coenzyme A epimerase: a key enzyme in the inversion metabolism of ibuprofen. Mol. Pharmacol. 1997, 51:576-582.
    • (1997) Mol. Pharmacol. , vol.51 , pp. 576-582
    • Reichel, C.1    Brugger, R.2    Bang, H.3    Geisslinger, G.4    Brune, K.5
  • 49
    • 33847697768 scopus 로고    scopus 로고
    • The catalysis of the 1,1-proton transfer by α-methyl-acyl-CoA racemase is coupled to a movement of the fatty acyl moiety over a hydrophobic, methionine-rich surface
    • Bhaumik P., Schmitz W., Hassinen A., Hiltunen J.K., Conzelmann E., Wierenga R.K. The catalysis of the 1,1-proton transfer by α-methyl-acyl-CoA racemase is coupled to a movement of the fatty acyl moiety over a hydrophobic, methionine-rich surface. J. Mol. Biol. 2007, 367:1145-1161.
    • (2007) J. Mol. Biol. , vol.367 , pp. 1145-1161
    • Bhaumik, P.1    Schmitz, W.2    Hassinen, A.3    Hiltunen, J.K.4    Conzelmann, E.5    Wierenga, R.K.6
  • 50
    • 0033987892 scopus 로고    scopus 로고
    • Enantiomer fractions are preferred to enantiomer ratios for describing chiral signatures in environmental analysis
    • Harner T., Wiberg K., Norstrom R. Enantiomer fractions are preferred to enantiomer ratios for describing chiral signatures in environmental analysis. Environ. Sci. Technol. 2000, 34:218-220.
    • (2000) Environ. Sci. Technol. , vol.34 , pp. 218-220
    • Harner, T.1    Wiberg, K.2    Norstrom, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.