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Volumn 70, Issue 1, 2006, Pages 53-59

Biotransformation of β-ionone by engineered cytochrome P450 BM-3

Author keywords

[No Author keywords available]

Indexed keywords

GENETIC ENGINEERING; HYDROXYLATION; MUTAGENESIS; SUBSTRATES;

EID: 32544456896     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-005-0028-4     Document Type: Article
Times cited : (81)

References (35)
  • 1
    • 0035876716 scopus 로고    scopus 로고
    • A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes
    • Appel D, Lutz-Wahl S, Fischer P, Schwaneberg U, Schmid RD (2001) A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J Biotechnol 88:167-171
    • (2001) J Biotechnol , vol.88 , pp. 167-171
    • Appel, D.1    Lutz-Wahl, S.2    Fischer, P.3    Schwaneberg, U.4    Schmid, R.D.5
  • 2
    • 0034819837 scopus 로고    scopus 로고
    • Protein engineering of Bacillus megaterium CYP102. The oxidation of polycyclic aromatic hydrocarbons
    • Carmichael AB, Wong LL (2001) Protein engineering of Bacillus megaterium CYP102. The oxidation of polycyclic aromatic hydrocarbons. Eur J Biochem 268:3117-3125
    • (2001) Eur J Biochem , vol.268 , pp. 3117-3125
    • Carmichael, A.B.1    Wong, L.L.2
  • 3
    • 0035264116 scopus 로고    scopus 로고
    • Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3
    • Cowart LA, Falck JR, Capdevila JH (2001) Structural determinants of active site binding affinity and metabolism by cytochrome P450 BM-3. Arch Biochem Biophys 387:117-124
    • (2001) Arch Biochem Biophys , vol.387 , pp. 117-124
    • Cowart, L.A.1    Falck, J.R.2    Capdevila, J.H.3
  • 4
    • 0025523428 scopus 로고
    • Floral attractants for the Cetoniinae and Rutelinae (Coleoptera: Scarabaeidae)
    • Donaldson JMI, McGovern TP, Ladd TLJ (1990) Floral attractants for the Cetoniinae and Rutelinae (Coleoptera: Scarabaeidae). J Econ Entomol 83:1298-1305
    • (1990) J Econ Entomol , vol.83 , pp. 1298-1305
    • Donaldson, J.M.I.1    McGovern, T.P.2    Ladd, T.L.J.3
  • 5
    • 0011480806 scopus 로고
    • Synthesis and structure of the enantiomeric 6-hydroxy-α-ionone and cis- and trans-5,6-dihydroxy-5,6-dihydro-β-ionone
    • Eschenmoser W, Uevelhart P, Eugster CH (1981) Synthesis and structure of the enantiomeric 6-hydroxy-α-ionone and cis- and trans-5,6-dihydroxy-5,6- dihydro-β-ionone. Helv Chim Acta 64:2681-2690
    • (1981) Helv Chim Acta , vol.64 , pp. 2681-2690
    • Eschenmoser, W.1    Uevelhart, P.2    Eugster, C.H.3
  • 7
    • 0036842594 scopus 로고    scopus 로고
    • Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase
    • Glieder A, Farinas ET, Arnold FH (2002) Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase. Nat Biotechnol 20:1135-1139
    • (2002) Nat Biotechnol , vol.20 , pp. 1135-1139
    • Glieder, A.1    Farinas, E.T.2    Arnold, F.H.3
  • 8
    • 0021138883 scopus 로고
    • On the stoichiometry of the oxidase and monooxygenase reactions catalyzed by liver microsomal cytochrome P-450. Products of oxygen reduction
    • Gorsky LD, Koop DR, Coon MJ (1984) On the stoichiometry of the oxidase and monooxygenase reactions catalyzed by liver microsomal cytochrome P-450. Products of oxygen reduction. J Biol Chem 259:6812-6817
    • (1984) J Biol Chem , vol.259 , pp. 6812-6817
    • Gorsky, L.D.1    Koop, D.R.2    Coon, M.J.3
  • 9
    • 0031021585 scopus 로고    scopus 로고
    • An active site substitution, F87V, converts cytochrome P450 BM-3 into a regio- and stereoselective (14S,15R)-arachidonic acid epoxygenase
    • Graham-Lorence S, Truan G, Peterson JA, Falck JR, Wei S, Helvig C, Capdevila JH (1997) An active site substitution, F87V, converts cytochrome P450 BM-3 into a regio- and stereoselective (14S,15R)-arachidonic acid epoxygenase. J Biol Chem 272:1127-1135
    • (1997) J Biol Chem , vol.272 , pp. 1127-1135
    • Graham-Lorence, S.1    Truan, G.2    Peterson, J.A.3    Falck, J.R.4    Wei, S.5    Helvig, C.6    Capdevila, J.H.7
  • 10
    • 84985084319 scopus 로고
    • Synthese von (-)-(R)-4-hydroxy-β-ionone and (-)-(5R,6S)-5-Hydroxy-4, 5-dihydro-α-ionone aus (-)-(S)-α-ionone
    • Haag A, Eschenmoser W, Eugster CH (1980) Synthese von (-)-(R)-4-hydroxy-β-ionone and (-)-(5R,6S)-5-Hydroxy-4,5-dihydro-α- ionone aus (-)-(S)-α-ionone. Helv Chim Acta 63:10-15
    • (1980) Helv Chim Acta , vol.63 , pp. 10-15
    • Haag, A.1    Eschenmoser, W.2    Eugster, C.H.3
  • 11
    • 0014843496 scopus 로고
    • Metabolism of β-ionone. Isolation, characterization and identification of the metabolites in the urine of rabbits
    • Ide H, Toki S (1970) Metabolism of β-ionone. Isolation, characterization and identification of the metabolites in the urine of rabbits. Biochem J 119:281-287
    • (1970) Biochem J , vol.119 , pp. 281-287
    • Ide, H.1    Toki, S.2
  • 12
    • 0011478549 scopus 로고
    • Biochemical preparation of optically active 4-hydroxy-β-ionone and its transformation to (S)-6-hydoxy-α-ionone
    • Kakeya H, Sugai T, Ohta H (1991) Biochemical preparation of optically active 4-hydroxy-β-ionone and its transformation to (S)-6-hydoxy-α- ionone. Agric Biol Chem 55:1873-1876
    • (1991) Agric Biol Chem , vol.55 , pp. 1873-1876
    • Kakeya, H.1    Sugai, T.2    Ohta, H.3
  • 13
    • 0041636293 scopus 로고
    • Fermentation of fragrances: Biotransformation of β-ionone by Lasiodiplodia theobromae
    • Krasnobajew V, Helmlinger D (1982) Fermentation of fragrances: biotransformation of β-ionone by Lasiodiplodia theobromae. Helv Chim Acta 65:1590-1601
    • (1982) Helv Chim Acta , vol.65 , pp. 1590-1601
    • Krasnobajew, V.1    Helmlinger, D.2
  • 14
    • 0031013972 scopus 로고    scopus 로고
    • The structure of the cytochrome P450 BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid
    • Li H, Poulos TL (1997) The structure of the cytochrome P450 BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nat Struct Biol 4:140-146
    • (1997) Nat Struct Biol , vol.4 , pp. 140-146
    • Li, H.1    Poulos, T.L.2
  • 15
    • 0035653258 scopus 로고    scopus 로고
    • Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons
    • Li QS, Ogawa J, Schmid RD, Shimizu S (2001a) Engineering cytochrome P450 BM-3 for oxidation of polycyclic aromatic hydrocarbons. Appl Environ Microbiol 67:5735-5739
    • (2001) Appl Environ Microbiol , vol.67 , pp. 5735-5739
    • Li, Q.S.1    Ogawa, J.2    Schmid, R.D.3    Shimizu, S.4
  • 16
    • 0035900342 scopus 로고    scopus 로고
    • Residue size at position 87 of cytochrome P450 BM-3 determines its stereoselectivity in propylbenzene and 3-chlorostyrene oxidation
    • Li QS, Ogawa J, Schmid RD, Shimizu S (2001b) Residue size at position 87 of cytochrome P450 BM-3 determines its stereoselectivity in propylbenzene and 3-chlorostyrene oxidation. FEBS Lett 508:249-252
    • (2001) FEBS Lett , vol.508 , pp. 249-252
    • Li, Q.S.1    Ogawa, J.2    Schmid, R.D.3    Shimizu, S.4
  • 19
    • 0242439281 scopus 로고    scopus 로고
    • Immobilisation of P450 BM-3 and an NADP+ cofactor recycling system: Towards a technical application of heme-containing monooxygenases in fine chemical synthesis
    • Maurer S, Urlacher V, Schulze H, Schmid RD (2003) Immobilisation of P450 BM-3 and an NADP+ cofactor recycling system: towards a technical application of heme-containing monooxygenases in fine chemical synthesis. Adv Synth Catal 345:802-810
    • (2003) Adv Synth Catal , vol.345 , pp. 802-810
    • Maurer, S.1    Urlacher, V.2    Schulze, H.3    Schmid, R.D.4
  • 20
    • 0035256945 scopus 로고    scopus 로고
    • Enhancement of attraction of α-ionol to male Bactrocera latifrons (Diptera: Tephritidae) by addition of a synergist, cade oil
    • McQuate GT, Peck SL (2001) Enhancement of attraction of α-ionol to male Bactrocera latifrons (Diptera: Tephritidae) by addition of a synergist, cade oil. J Econ Entomol 94:39-46
    • (2001) J Econ Entomol , vol.94 , pp. 39-46
    • McQuate, G.T.1    Peck, S.L.2
  • 21
    • 0022878676 scopus 로고
    • Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium
    • Narhi LO, Fulco AJ (1986) Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J Biol Chem 261:7160-7169
    • (1986) J Biol Chem , vol.261 , pp. 7160-7169
    • Narhi, L.O.1    Fulco, A.J.2
  • 22
    • 0023806175 scopus 로고
    • Characterization of the protein expressed in Escherichia coli by a recombinant plasmid containing the Bacillus megaterium cytochrome P-450 BM-3 gene
    • Narhi LO, Wen LP, Fulco AJ (1988) Characterization of the protein expressed in Escherichia coli by a recombinant plasmid containing the Bacillus megaterium cytochrome P-450 BM-3 gene. Mol Cell Biochem 79:63-71
    • (1988) Mol Cell Biochem , vol.79 , pp. 63-71
    • Narhi, L.O.1    Wen, L.P.2    Fulco, A.J.3
  • 23
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I Evidence for its hemoprotein nature
    • Omura T, Sato RJ (1964) The carbon monoxide-binding pigment of liver microsomes. I Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.J.2
  • 24
    • 24144450535 scopus 로고
    • Biological activity and structure of abscisic acid
    • Oritani T, Yamashita K (1984) Biological activity and structure of abscisic acid. Kagaku to Seibutsu 22:21-28
    • (1984) Kagaku to Seibutsu , vol.22 , pp. 21-28
    • Oritani, T.1    Yamashita, K.2
  • 25
    • 0242330792 scopus 로고    scopus 로고
    • Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3
    • Peters MW, Meinhold P, Glieder A, Arnold FH (2003) Regio- and enantioselective alkane hydroxylation with engineered cytochromes P450 BM-3. J Am Chem Soc 125:13442-13450
    • (2003) J Am Chem Soc , vol.125 , pp. 13442-13450
    • Peters, M.W.1    Meinhold, P.2    Glieder, A.3    Arnold, F.H.4
  • 28
    • 84970547135 scopus 로고
    • Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits
    • Sefton MA, Skouroumounis GK, Massy-Westropp RA, Williams PJ (1989) Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits. Aust J Chem 42:2071-2084
    • (1989) Aust J Chem , vol.42 , pp. 2071-2084
    • Sefton, M.A.1    Skouroumounis, G.K.2    Massy-Westropp, R.A.3    Williams, P.J.4
  • 29
    • 0033579488 scopus 로고    scopus 로고
    • The FMN to heme electron transfer in cytochrome P450 BM-3. Effect of chemical modification of cysteines engineered at the FMN-heme domain interaction site
    • Sevrioukova IF, Hazzard JT, Tollin G, Poulos TL (1999) The FMN to heme electron transfer in cytochrome P450 BM-3. Effect of chemical modification of cysteines engineered at the FMN-heme domain interaction site. J Biol Chem 274:36097-36106
    • (1999) J Biol Chem , vol.274 , pp. 36097-36106
    • Sevrioukova, I.F.1    Hazzard, J.T.2    Tollin, G.3    Poulos, T.L.4
  • 30
    • 0024961849 scopus 로고
    • Microbial conversion of β-ionone by immobilized Aspergillus niger in the presence of an organic solvent
    • Sode K, Karube I, Araki R, Mikami Y (1989) Microbial conversion of β-ionone by immobilized Aspergillus niger in the presence of an organic solvent. Biotechnol Bioeng 33:1191-1195
    • (1989) Biotechnol Bioeng , vol.33 , pp. 1191-1195
    • Sode, K.1    Karube, I.2    Araki, R.3    Mikami, Y.4
  • 31
    • 11844256914 scopus 로고    scopus 로고
    • Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450 BM-3
    • Sowden RJ, Yasmin S, Rees NH, Bell SG, Wong LL (2005) Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450 BM-3. Org Biomol Chem 3:57-64
    • (2005) Org Biomol Chem , vol.3 , pp. 57-64
    • Sowden, R.J.1    Yasmin, S.2    Rees, N.H.3    Bell, S.G.4    Wong, L.L.5
  • 32
    • 32544453799 scopus 로고    scopus 로고
    • Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds
    • Epub ahead of print
    • Sulistyaningdyah WT, Ogawa J, Li QS, Maeda C, Yano Y, Schmid RD, Shimizu S (2004) Hydroxylation activity of P450 BM-3 mutant F87V towards aromatic compounds and its application to the synthesis of hydroquinone derivatives from phenolic compounds. Appl Microbiol Biotechnol [Epub ahead of print]
    • (2004) Appl Microbiol Biotechnol
    • Sulistyaningdyah, W.T.1    Ogawa, J.2    Li, Q.S.3    Maeda, C.4    Yano, Y.5    Schmid, R.D.6    Shimizu, S.7
  • 33
    • 0033563872 scopus 로고    scopus 로고
    • P450BM-3: Absolute configuration of the primary metabolites of palmitic acid
    • Truan G, Komandla MR, Falck JR, Peterson JA (1999) P450BM-3: absolute configuration of the primary metabolites of palmitic acid. Arch Biochem Biophys 366:192-198
    • (1999) Arch Biochem Biophys , vol.366 , pp. 192-198
    • Truan, G.1    Komandla, M.R.2    Falck, J.R.3    Peterson, J.A.4
  • 34
    • 0023929638 scopus 로고
    • A simple and rapid method for the selection of oligodeoxynucleotide- directed mutants
    • Vandeyar MA, Weiner MP, Hutton CJ, Batt CA (1988) A simple and rapid method for the selection of oligodeoxynucleotide-directed mutants. Gene 65:129-133
    • (1988) Gene , vol.65 , pp. 129-133
    • Vandeyar, M.A.1    Weiner, M.P.2    Hutton, C.J.3    Batt, C.A.4
  • 35
    • 32544447844 scopus 로고    scopus 로고
    • Process for oxidising terpenes. European Patent WO 00/31273, 2 June 2000
    • Wong LL, Bell SG, Carmichael AB (2000) Process for oxidising terpenes. European Patent WO 00/31273, 2 June 2000
    • (2000)
    • Wong, L.L.1    Bell, S.G.2    Carmichael, A.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.