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Volumn 52, Issue 6-7, 2013, Pages 370-376

Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase

Author keywords

Biocatalysis; Heme thiolate; Oxygenation; Peroxygenase; Stereoselective

Indexed keywords

2 ,3-DIMETHYL-2-BUTENE; BIOCATALYSIS; BIOTECHNOLOGICAL APPROACHES; CHEMICAL BUILDING BLOCKS; HEME-THIOLATE; MICHAELIS-MENTEN CONSTANT; PEROXYGENASE; STEREO-SELECTIVE;

EID: 84876743333     PISSN: 01410229     EISSN: 18790909     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2013.02.013     Document Type: Article
Times cited : (61)

References (51)
  • 1
    • 84856091958 scopus 로고    scopus 로고
    • Mesoporous SBA-15 modified with manganese pyrazolylpyridine complexes for the catalytic epoxidation of terminal alkenes
    • Tang J., Zu Y., Huo W., Wang L., Wang J., Jia M., et al. Mesoporous SBA-15 modified with manganese pyrazolylpyridine complexes for the catalytic epoxidation of terminal alkenes. Journal of Molecular Catalysis A: Chemical 2011, 355:201-209.
    • (2011) Journal of Molecular Catalysis A: Chemical , vol.355 , pp. 201-209
    • Tang, J.1    Zu, Y.2    Huo, W.3    Wang, L.4    Wang, J.5    Jia, M.6
  • 2
    • 74549171651 scopus 로고    scopus 로고
    • Asymmetric counteranion-directed transition-metal catalysis: enantioselective epoxidation of alkenes with manganese(III) salen phosphate complexes
    • Liao S., List B. Asymmetric counteranion-directed transition-metal catalysis: enantioselective epoxidation of alkenes with manganese(III) salen phosphate complexes. Angewandte Chemie International Edition 2010, 49:628-631.
    • (2010) Angewandte Chemie International Edition , vol.49 , pp. 628-631
    • Liao, S.1    List, B.2
  • 3
    • 84857548597 scopus 로고    scopus 로고
    • Enantioselective synthesis of 2,2-disubstituted terminal epoxides via catalytic asymmetric Corey-Chaykovsky epoxidation of ketones
    • Sone T., Yamaguchi A., Matsunaga S., Shibasaki M. Enantioselective synthesis of 2,2-disubstituted terminal epoxides via catalytic asymmetric Corey-Chaykovsky epoxidation of ketones. Molecules 2012, 17:1617-1634.
    • (2012) Molecules , vol.17 , pp. 1617-1634
    • Sone, T.1    Yamaguchi, A.2    Matsunaga, S.3    Shibasaki, M.4
  • 4
    • 84859184531 scopus 로고    scopus 로고
    • Biomimetic epoxidation of alkenes with sodium periodate catalyzed by tetraphenylporphyrinatomanganese(III) chloride supported on multiwall carbon nanotubes
    • Zakeri M., Moghadam M., Mohammadpoor-Baltork I., Tangestaninejad S., Mirkhani V., Khosropour A., et al. Biomimetic epoxidation of alkenes with sodium periodate catalyzed by tetraphenylporphyrinatomanganese(III) chloride supported on multiwall carbon nanotubes. Transition Metal Chemistry 2012, 37:45-53.
    • (2012) Transition Metal Chemistry , vol.37 , pp. 45-53
    • Zakeri, M.1    Moghadam, M.2    Mohammadpoor-Baltork, I.3    Tangestaninejad, S.4    Mirkhani, V.5    Khosropour, A.6
  • 5
    • 0030798603 scopus 로고    scopus 로고
    • Synthesis of enantiopure epoxides through biocatalytic approaches
    • Archelas A., Furstoss R. Synthesis of enantiopure epoxides through biocatalytic approaches. Annual Review of Microbiology 1997, 51:491-525.
    • (1997) Annual Review of Microbiology , vol.51 , pp. 491-525
    • Archelas, A.1    Furstoss, R.2
  • 8
    • 0015919241 scopus 로고
    • Enzymatic epoxidation: II. Comparison between the epoxidation and hydroxylation reactions catalyzed by the ω-hydroxylation system of Pseudomonas oleovorans
    • May S.W., Abbott B.J. Enzymatic epoxidation: II. Comparison between the epoxidation and hydroxylation reactions catalyzed by the ω-hydroxylation system of Pseudomonas oleovorans. The Journal of Biological Chemistry 1973, 248:1725-1730.
    • (1973) The Journal of Biological Chemistry , vol.248 , pp. 1725-1730
    • May, S.W.1    Abbott, B.J.2
  • 9
    • 0025008988 scopus 로고
    • Epoxidation of gaseous alkenes by a Rhodococcus sp
    • Woods N.R., Murrell J.C. Epoxidation of gaseous alkenes by a Rhodococcus sp. Biotechnology Letters 1990, 12:409-414.
    • (1990) Biotechnology Letters , vol.12 , pp. 409-414
    • Woods, N.R.1    Murrell, J.C.2
  • 11
    • 31344438135 scopus 로고    scopus 로고
    • Enantioselective epoxidation of terminal alkenes to (R)- and (S)-epoxides by engineered cytochromes P450 BM-3
    • Kubo T., Meinhold P., Peters M.W., Arnold F.H. Enantioselective epoxidation of terminal alkenes to (R)- and (S)-epoxides by engineered cytochromes P450 BM-3. Chemistry - A European Journal 2006, 12:1216-1220.
    • (2006) Chemistry - A European Journal , vol.12 , pp. 1216-1220
    • Kubo, T.1    Meinhold, P.2    Peters, M.W.3    Arnold, F.H.4
  • 12
    • 0029941844 scopus 로고    scopus 로고
    • Chloroperoxidase as enantioselective epoxidation catalyst: an efficient synthesis of (R)-(-)-mevalonolactone
    • Lakner F.J., Hager L.P. Chloroperoxidase as enantioselective epoxidation catalyst: an efficient synthesis of (R)-(-)-mevalonolactone. The Journal of Organic Chemistry 1996, 61:3923-3925.
    • (1996) The Journal of Organic Chemistry , vol.61 , pp. 3923-3925
    • Lakner, F.J.1    Hager, L.P.2
  • 13
    • 42449157733 scopus 로고    scopus 로고
    • Models and mechanisms of cytochrome P450 action
    • Springer, US, pp.
    • Ortiz de Montellano P.R., Groves J.T. Models and mechanisms of cytochrome P450 action. Cytochrome P450 2005, Springer, US, pp. 1-43.
    • (2005) Cytochrome P450 , pp. 1-43
    • Ortiz de Montellano, P.R.1    Groves, J.T.2
  • 16
    • 77953151732 scopus 로고    scopus 로고
    • Crystallization of a 45kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron
    • Piontek K., Ullrich R., Liers C., Diederichs K., Plattner D.A., Hofrichter M. Crystallization of a 45kDa peroxygenase/peroxidase from the mushroom Agrocybe aegerita and structure determination by SAD utilizing only the haem iron. Acta Crystallographica Section F 2010, 66:693-698.
    • (2010) Acta Crystallographica Section F , vol.66 , pp. 693-698
    • Piontek, K.1    Ullrich, R.2    Liers, C.3    Diederichs, K.4    Plattner, D.A.5    Hofrichter, M.6
  • 20
    • 80052617631 scopus 로고    scopus 로고
    • New trends in fungal biooxidation
    • Springer, Heidelberg, M. Hofrichter, K. Esser (Eds.)
    • Hofrichter M., Ullrich R. New trends in fungal biooxidation. MYCOTA X - Industrial Applications 2010, 425-449. Springer, Heidelberg. 2nd ed. M. Hofrichter, K. Esser (Eds.).
    • (2010) MYCOTA X - Industrial Applications , pp. 425-449
    • Hofrichter, M.1    Ullrich, R.2
  • 21
  • 22
    • 80052960977 scopus 로고    scopus 로고
    • Selective hydroxylation of alkanes by an extracellular fungal peroxygenase
    • Peter S., Kinne M., Wang X., Ullrich R., Kayser G., Groves J.T., et al. Selective hydroxylation of alkanes by an extracellular fungal peroxygenase. FEBS Journal 2011, 278:3667-3675.
    • (2011) FEBS Journal , vol.278 , pp. 3667-3675
    • Peter, S.1    Kinne, M.2    Wang, X.3    Ullrich, R.4    Kayser, G.5    Groves, J.T.6
  • 23
    • 77950459712 scopus 로고    scopus 로고
    • Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases
    • Aranda E., Ullrich R., Hofrichter M. Conversion of polycyclic aromatic hydrocarbons, methyl naphthalenes and dibenzofuran by two fungal peroxygenases. Biodegradation 2009, 21:267-281.
    • (2009) Biodegradation , vol.21 , pp. 267-281
    • Aranda, E.1    Ullrich, R.2    Hofrichter, M.3
  • 25
    • 50049104412 scopus 로고    scopus 로고
    • Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase
    • Kinne M., Ullrich R., Hammel K.E., Scheibner K., Hofrichter M. Regioselective preparation of (R)-2-(4-hydroxyphenoxy)propionic acid with a fungal peroxygenase. Tetrahedron Letters 2008, 49:5950-5953.
    • (2008) Tetrahedron Letters , vol.49 , pp. 5950-5953
    • Kinne, M.1    Ullrich, R.2    Hammel, K.E.3    Scheibner, K.4    Hofrichter, M.5
  • 26
    • 84857157629 scopus 로고    scopus 로고
    • Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita
    • Kluge M., Ullrich R., Scheibner K., Hofrichter M. Stereoselective benzylic hydroxylation of alkylbenzenes and epoxidation of styrene derivatives catalyzed by the peroxygenase of Agrocybe aegerita. Green Chemistry 2012, 14:440-446.
    • (2012) Green Chemistry , vol.14 , pp. 440-446
    • Kluge, M.1    Ullrich, R.2    Scheibner, K.3    Hofrichter, M.4
  • 27
    • 63949083769 scopus 로고    scopus 로고
    • Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases
    • Aranda E., Kinne M., Kluge M., Ullrich R., Hofrichter M. Conversion of dibenzothiophene by the mushrooms Agrocybe aegerita and Coprinellus radians and their extracellular peroxygenases. Applied Microbiology and Biotechnology 2008, 82:1057-1066.
    • (2008) Applied Microbiology and Biotechnology , vol.82 , pp. 1057-1066
    • Aranda, E.1    Kinne, M.2    Kluge, M.3    Ullrich, R.4    Hofrichter, M.5
  • 28
    • 56649124574 scopus 로고    scopus 로고
    • Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita
    • Ullrich R., Dolge C., Kluge M., Hofrichter M. Pyridine as novel substrate for regioselective oxygenation with aromatic peroxygenase from Agrocybe aegerita. FEBS Letters 2008, 582:4100-4106.
    • (2008) FEBS Letters , vol.582 , pp. 4100-4106
    • Ullrich, R.1    Dolge, C.2    Kluge, M.3    Hofrichter, M.4
  • 30
    • 80052611090 scopus 로고    scopus 로고
    • Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase
    • Kinne M., Poraj-Kobielska M., Ullrich R., Nousiainen P., Sipilä J., Scheibner K., et al. Oxidative cleavage of non-phenolic β-O-4 lignin model dimers by an extracellular aromatic peroxygenase. Holzforschung 2011, 65:673-679.
    • (2011) Holzforschung , vol.65 , pp. 673-679
    • Kinne, M.1    Poraj-Kobielska, M.2    Ullrich, R.3    Nousiainen, P.4    Sipilä, J.5    Scheibner, K.6
  • 32
    • 0031856715 scopus 로고    scopus 로고
    • An EXCEL template for calculation of enzyme kinetic parameters by non-linear regression
    • Hernandez A., Ruiz M.T. An EXCEL template for calculation of enzyme kinetic parameters by non-linear regression. Bioinformatics 1998, 14:227-228.
    • (1998) Bioinformatics , vol.14 , pp. 227-228
    • Hernandez, A.1    Ruiz, M.T.2
  • 34
    • 0025063205 scopus 로고
    • Suicide inactivation of cytochrome P-450 model compounds by terminal olefins. 1. A mechanistic study of heme N-alkylation and epoxidation
    • Collman J.P., Hampton P.D., Brauman J.T. Suicide inactivation of cytochrome P-450 model compounds by terminal olefins. 1. A mechanistic study of heme N-alkylation and epoxidation. Journal of the American Chemical Society 1990, 112:2977-2986.
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 2977-2986
    • Collman, J.P.1    Hampton, P.D.2    Brauman, J.T.3
  • 35
    • 0025090933 scopus 로고
    • Suicide inactivation of cytochrome P-450 model compounds by terminal olefins, 2. Steric and electronic effects in heme N-alkylation and epoxidation
    • Collman J.P., Hampton P.D., Brauman J.I. Suicide inactivation of cytochrome P-450 model compounds by terminal olefins, 2. Steric and electronic effects in heme N-alkylation and epoxidation. Journal of the American Chemical Society 1990, 112:2986-2998.
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 2986-2998
    • Collman, J.P.1    Hampton, P.D.2    Brauman, J.I.3
  • 36
    • 33644515399 scopus 로고    scopus 로고
    • Inhibition of cytochrome P450 enzymes
    • Kluwer Academic/Plenum Publishers, New York, Montellano PROd (Ed.)
    • Correia M.A., Montellano P.R.O.d. Inhibition of cytochrome P450 enzymes. Cytochrome P450: structure, mechanism, and biochemistry 2005, 267-272. Kluwer Academic/Plenum Publishers, New York. 3rd ed. Montellano PROd (Ed.).
    • (2005) Cytochrome P450: structure, mechanism, and biochemistry , pp. 267-272
    • Correia, M.A.1    Montellano, P.2
  • 37
    • 0029103571 scopus 로고
    • Transient heme N-alkylation of chloroperoxidase by terminal alkenes and alkynes
    • Dexter A.F., Hager L.P. Transient heme N-alkylation of chloroperoxidase by terminal alkenes and alkynes. Journal of the American Chemical Society 1995, 117:817-818.
    • (1995) Journal of the American Chemical Society , vol.117 , pp. 817-818
    • Dexter, A.F.1    Hager, L.P.2
  • 39
    • 0036239908 scopus 로고    scopus 로고
    • Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes
    • Miyazawa M., Shindo M., Shimada T. Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Drug Metabolism and Disposition 2002, 30:602-607.
    • (2002) Drug Metabolism and Disposition , vol.30 , pp. 602-607
    • Miyazawa, M.1    Shindo, M.2    Shimada, T.3
  • 40
    • 0019466150 scopus 로고
    • A comparative study on the metabolism of d-limonene and 4-vinylcyclohex-1-ene by hepatic microsomes
    • Watabe T., Hiratsuka A., Ozawa N., Isobe M. A comparative study on the metabolism of d-limonene and 4-vinylcyclohex-1-ene by hepatic microsomes. Xenobiotica 1981, 11:333-344.
    • (1981) Xenobiotica , vol.11 , pp. 333-344
    • Watabe, T.1    Hiratsuka, A.2    Ozawa, N.3    Isobe, M.4
  • 42
    • 0026763155 scopus 로고
    • Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene
    • Crowell P.L., Kennan W.S., Haag J.D., Ahmad S., Vedejs E., Gould M.N. Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene. Carcinogenesis 1992, 13:1261-1264.
    • (1992) Carcinogenesis , vol.13 , pp. 1261-1264
    • Crowell, P.L.1    Kennan, W.S.2    Haag, J.D.3    Ahmad, S.4    Vedejs, E.5    Gould, M.N.6
  • 43
    • 0036324584 scopus 로고    scopus 로고
    • Carvone and perillaldehyde interfere with the serum-induced formation of filamentous structures in Candida albicans at substantially lower concentrations than those causing significant inhibition of growth
    • McGeady P., Wansley D.L., Logan D.A. Carvone and perillaldehyde interfere with the serum-induced formation of filamentous structures in Candida albicans at substantially lower concentrations than those causing significant inhibition of growth. Journal of Natural Products 2002, 65:953-955.
    • (2002) Journal of Natural Products , vol.65 , pp. 953-955
    • McGeady, P.1    Wansley, D.L.2    Logan, D.A.3
  • 44
    • 0346964466 scopus 로고    scopus 로고
    • Alkene epoxidation catalyzed by cytochrome P450 BM-3 139-3
    • Farinas E.T., Alcalde M., Arnold F. Alkene epoxidation catalyzed by cytochrome P450 BM-3 139-3. Tetrahedron 2004, 60:525-528.
    • (2004) Tetrahedron , vol.60 , pp. 525-528
    • Farinas, E.T.1    Alcalde, M.2    Arnold, F.3
  • 45
    • 70350381550 scopus 로고    scopus 로고
    • Effect of porphyrin ligands on the regioselective dehydrogenation versus epoxidation of olefins by oxoiron(IV) mimics of cytochrome P450
    • Kumar D., Tahsini L., Pd Visser S., Kang H.Y., Kim S.J., Nam W. Effect of porphyrin ligands on the regioselective dehydrogenation versus epoxidation of olefins by oxoiron(IV) mimics of cytochrome P450. Journal of Physical Chemistry A 2009, 113:11713-11722.
    • (2009) Journal of Physical Chemistry A , vol.113 , pp. 11713-11722
    • Kumar, D.1    Tahsini, L.2    Pd, V.S.3    Kang, H.Y.4    Kim, S.J.5    Nam, W.6
  • 48
    • 0016390626 scopus 로고
    • Stereoselective epoxidation of octadiene catalyzed by an enzyme system of Pseudomonas oleovorans
    • May S.W., Schwartz R.D. Stereoselective epoxidation of octadiene catalyzed by an enzyme system of Pseudomonas oleovorans. Journal of the American Chemical Society 1974, 96:4031-4032.
    • (1974) Journal of the American Chemical Society , vol.96 , pp. 4031-4032
    • May, S.W.1    Schwartz, R.D.2
  • 51
    • 14244251991 scopus 로고    scopus 로고
    • Characterization of the polyene macrolide P450 epoxidase from Streptomyces natalensis that converts de-epoxypimaricin into pimaricin
    • Mendes M.V., Antón N., Martín J.F., Aparicio J.F. Characterization of the polyene macrolide P450 epoxidase from Streptomyces natalensis that converts de-epoxypimaricin into pimaricin. Biochemical Journal 2005, 386:57-62.
    • (2005) Biochemical Journal , vol.386 , pp. 57-62
    • Mendes, M.V.1    Antón, N.2    Martín, J.F.3    Aparicio, J.F.4


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