메뉴 건너뛰기




Volumn 59, Issue 2, 1998, Pages 171-177

Enantioselective hydroxylation of 4-alkylphenols by vanillyl alcohol oxidase

Author keywords

4 alkylphenols; 4 vinylphenol; Covalent flavoprotein; Enantioselectivity; Vanillyl alcohol oxidase

Indexed keywords

ALCOHOLS; BIOCONVERSION; CATALYSIS; CATALYST SELECTIVITY; HYDROXYLATION; PHENOLS; SUBSTRATES;

EID: 0032551601     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19980720)59:2<171::AID-BIT5>3.0.CO;2-E     Document Type: Article
Times cited : (37)

References (26)
  • 1
    • 0024358519 scopus 로고
    • Anaerobic oxidation of p-cresol mediated by a partially purified methylhydroxylase from a denitrifying bacterium
    • Bossert, I. D., Whited, G., Gibson, D. T., Young, L. Y. 1989. Anaerobic oxidation of p-cresol mediated by a partially purified methylhydroxylase from a denitrifying bacterium. J. Bacteriol. 171: 2956-2962.
    • (1989) J. Bacteriol. , vol.171 , pp. 2956-2962
    • Bossert, I.D.1    Whited, G.2    Gibson, D.T.3    Young, L.Y.4
  • 2
    • 0028665168 scopus 로고
    • Evaluation of D-amino acid oxidase from Rhodotorula gracilis for the production of α-keto acids: A reactor system
    • Butò, S., Pollegioni, L., D'Angurio, L., Pilone, M. S. 1994. Evaluation of D-amino acid oxidase from Rhodotorula gracilis for the production of α-keto acids: A reactor system. Biotechnol. Bioeng. 44: 1288-1294.
    • (1994) Biotechnol. Bioeng. , vol.44 , pp. 1288-1294
    • Butò, S.1    Pollegioni, L.2    D'Angurio, L.3    Pilone, M.S.4
  • 3
    • 0025759183 scopus 로고
    • Synthesis of optically active compounds: A large scale perspective
    • Crosby, J, 1991. Synthesis of optically active compounds: A large scale perspective. Tetrahedron 47: 4789-4841.
    • (1991) Tetrahedron , vol.47 , pp. 4789-4841
    • Crosby, J.1
  • 5
    • 0026665175 scopus 로고
    • Purification and characterization of vanillyl-alcohol oxidase from Penicillium simplicissimum
    • de Jong, E., van Berkel, W. J. H., van der Zwan, R. P., de Bont, J. A. M. 1992. Purification and characterization of vanillyl-alcohol oxidase from Penicillium simplicissimum. Eur. J. Biochem. 208: 651-657.
    • (1992) Eur. J. Biochem. , vol.208 , pp. 651-657
    • De Jong, E.1    Van Berkel, W.J.H.2    Van Der Zwan, R.P.3    De Bont, J.A.M.4
  • 6
    • 0028985653 scopus 로고
    • The biotransformation of simple phenolic compounds by Brettanomyces anomalus
    • Edlin, D. A. N., Narbad, A., Dickinson, J. R., Lloyd, D. 1995. The biotransformation of simple phenolic compounds by Brettanomyces anomalus. FEMS Microbiol. Lett. 125: 311-316.
    • (1995) FEMS Microbiol. Lett. , vol.125 , pp. 311-316
    • Edlin, D.A.N.1    Narbad, A.2    Dickinson, J.R.3    Lloyd, D.4
  • 7
    • 37049079343 scopus 로고
    • A facile general route to enantiomeric l-(4′-hydroxyphenyl)alkanols, and an improved synthesis of 4-vinylphenol
    • Everhart, E. T., Craig, J. C. 1991. A facile general route to enantiomeric l-(4′-hydroxyphenyl)alkanols, and an improved synthesis of 4-vinylphenol. J. Chem. Soc., Perkin Trans. 1, 1701-1707.
    • (1991) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1701-1707
    • Everhart, E.T.1    Craig, J.C.2
  • 8
    • 0028852139 scopus 로고
    • Substrate specificity of flavin-dependent vanillyl alcohol oxidase from Penicillium simplicissimum
    • Fraaije, M. W., Veeger, C., van Berkel, W. J. H. 1995. Substrate specificity of flavin-dependent vanillyl alcohol oxidase from Penicillium simplicissimum. Eur. J. Biochem. 234: 271-277.
    • (1995) Eur. J. Biochem. , vol.234 , pp. 271-277
    • Fraaije, M.W.1    Veeger, C.2    Van Berkel, W.J.H.3
  • 9
    • 2642662192 scopus 로고    scopus 로고
    • Vanillyl-alcohol oxidase from Penicillium simplicissimum: Reactivity with p-cresol and preliminary structural analysis
    • K. Stevenson, V. Massey, and Ch. Williams, Jr. (eds.). University Press, Calgary, Canada
    • Fraaije, M. W., Drijfhout, F. P., Meulenbelt, G., van Berkel, W. J. H. 1997. Vanillyl-alcohol oxidase from Penicillium simplicissimum: Reactivity with p-cresol and preliminary structural analysis, pp. 261-264. In: K. Stevenson, V. Massey, and Ch. Williams, Jr. (eds.), Flavins and Flavoproteins XII. University Press, Calgary, Canada.
    • (1997) Flavins and Flavoproteins XII , pp. 261-264
    • Fraaije, M.W.1    Drijfhout, F.P.2    Meulenbelt, G.3    Van Berkel, W.J.H.4
  • 10
    • 0030739371 scopus 로고    scopus 로고
    • Catalytic mechanism of the oxidative demethylation of 4-(methoxymethyl)phenol by vanillyl-alcohol oxidase
    • Fraaije, M. W., van Berkel, W. J. H. 1997. Catalytic mechanism of the oxidative demethylation of 4-(methoxymethyl)phenol by vanillyl-alcohol oxidase. J. Biol. Chem. 272: 18111-18116.
    • (1997) J. Biol. Chem. , vol.272 , pp. 18111-18116
    • Fraaije, M.W.1    Van Berkel, W.J.H.2
  • 11
    • 0017227025 scopus 로고
    • The hydroxylation of p-cresol and its conversion to p-hydroxybenzaldehyde in Pseudomonas putida
    • Hopper, D. J. 1976. The hydroxylation of p-cresol and its conversion to p-hydroxybenzaldehyde in Pseudomonas putida. Biochem. Biophys. Res. Commun. 69: 462-468.
    • (1976) Biochem. Biophys. Res. Commun. , vol.69 , pp. 462-468
    • Hopper, D.J.1
  • 12
    • 0018195707 scopus 로고
    • 18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida
    • 18O]water in the formation of p-hydroxybenzyl alcohol by the p-cresol methylhydroxylase from Pseudomonas putida. Biochem. J. 175: 345-347.
    • (1978) Biochem. J. , vol.175 , pp. 345-347
    • Hopper, D.J.1
  • 13
    • 33751499686 scopus 로고
    • A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia and lipase from Candida rugosa
    • Kazlauskas, R. J., Weissfloch, A. N. E., Rappaport A. T., Cuccia, L. A. 1991. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia and lipase from Candida rugosa. J. Org. Chem. 56: 2656-2665.
    • (1991) J. Org. Chem. , vol.56 , pp. 2656-2665
    • Kazlauskas, R.J.1    Weissfloch, A.N.E.2    Rappaport, A.T.3    Cuccia, L.A.4
  • 14
    • 0026071385 scopus 로고
    • Three-dimensional structure of p-cresol methylhydroxylase (flavocytochrome c) from Pseudomonas putida at 3.0 Å resolution
    • Mathews, F. S., Chen, Z.-W., Bellamy, H. D., McIntire, W. S. 1991. Three-dimensional structure of p-cresol methylhydroxylase (flavocytochrome c) from Pseudomonas putida at 3.0 Å resolution. Biochemistry 30: 238-247.
    • (1991) Biochemistry , vol.30 , pp. 238-247
    • Mathews, F.S.1    Chen, Z.-W.2    Bellamy, H.D.3    McIntire, W.S.4
  • 15
    • 0031571090 scopus 로고    scopus 로고
    • Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: The shape of the active-site cavity controls substrate specificity
    • Mattevi, A., Fraaije, M. W., Mozarelli, A., Olivi, L., Coda, A., van Berkel, W. J. H. 1997. Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity. Structure 5: 907-920.
    • (1997) Structure , vol.5 , pp. 907-920
    • Mattevi, A.1    Fraaije, M.W.2    Mozarelli, A.3    Olivi, L.4    Coda, A.5    Van Berkel, W.J.H.6
  • 16
    • 0021666137 scopus 로고
    • Stereochemistry of 1-(4′-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase
    • McIntire, W. S., Hopper, D. J., Craig, J. C., Everhart, E. T., Webster, R. V., Causer, M. J., Singer, T. P. 1984. Stereochemistry of 1-(4′-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase. Biochem. J. 224: 617-621.
    • (1984) Biochem. J. , vol.224 , pp. 617-621
    • McIntire, W.S.1    Hopper, D.J.2    Craig, J.C.3    Everhart, E.T.4    Webster, R.V.5    Causer, M.J.6    Singer, T.P.7
  • 17
    • 0037560441 scopus 로고
    • The chemical and stereochemical course of oxidation of 4-ethylphenol and other 4-alkylphenols by p-cresol methylhydroxylase
    • D. E. Edmondson and D. B. McCormick (eds.). W. de Gruyter, Berlin
    • McIntire, W. S., Bohmont, C. 1987. The chemical and stereochemical course of oxidation of 4-ethylphenol and other 4-alkylphenols by p-cresol methylhydroxylase, pp. 677-686. In: D. E. Edmondson and D. B. McCormick (eds.), Flavins and Flavoproteins IX. W. de Gruyter, Berlin.
    • (1987) Flavins and Flavoproteins IX , pp. 677-686
    • McIntire, W.S.1    Bohmont, C.2
  • 18
    • 0024430224 scopus 로고
    • The purification and characterization of 4-ethylphenol methylhydroxylase, a flavoprotein from Pseudomonas putida JD1
    • Reeve, C. D., Carver, M. A., Hopper, D. J. 1989. The purification and characterization of 4-ethylphenol methylhydroxylase, a flavoprotein from Pseudomonas putida JD1. Biochem. J. 263: 431-437.
    • (1989) Biochem. J. , vol.263 , pp. 431-437
    • Reeve, C.D.1    Carver, M.A.2    Hopper, D.J.3
  • 19
    • 0025309994 scopus 로고
    • Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme 4-ethylphenol methylenehydroxylase
    • Reeve, C. D., Carver, M. A., Hopper, D. J. 1990. Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme 4-ethylphenol methylenehydroxylase. Biochem. J. 269: 815-819.
    • (1990) Biochem. J. , vol.269 , pp. 815-819
    • Reeve, C.D.1    Carver, M.A.2    Hopper, D.J.3
  • 22
    • 0028831731 scopus 로고
    • Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: Relationship to toxicity
    • Thompson, D. C., Perera, K., London, R. 1995. Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: Relationship to toxicity. Chem. Res. Toxicol. 8: 55-60.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 55-60
    • Thompson, D.C.1    Perera, K.2    London, R.3
  • 23
    • 0029417196 scopus 로고
    • Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols
    • Uppenberg, J., Öhrner, N., Norin, M., Hult, K., Kleywegt, G. J., Patkar, S., Waagen, V., Anthonsen, T., Jones, T. A. 1995. Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry 34: 16838-16851.
    • (1995) Biochemistry , vol.34 , pp. 16838-16851
    • Uppenberg, J.1    Öhrner, N.2    Norin, M.3    Hult, K.4    Kleywegt, G.J.5    Patkar, S.6    Waagen, V.7    Anthonsen, T.8    Jones, T.A.9
  • 25
  • 26
    • 0028855317 scopus 로고
    • Chloroperoxidase-catalyzed asymmetric oxidations: Substrate specificity and mechanistic study
    • Zaks, A., Dodds, D. R. 1995. Chloroperoxidase-catalyzed asymmetric oxidations: Substrate specificity and mechanistic study. J. Am. Chem. Soc. 117: 10419-10424.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10419-10424
    • Zaks, A.1    Dodds, D.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.