메뉴 건너뛰기




Volumn 108, Issue 12, 2011, Pages 2815-2822

Tolerance of β-diketone hydrolases as representatives of the crotonase superfamily towards organic solvents

Author keywords

diketone hydrolase; Crotonase superfamily; Enzyme stability; Hydrolysis; Solvent effects; Solvent tolerance

Indexed keywords

CROTONASE SUPERFAMILY; DIKETONES; ENZYME STABILITY; SOLVENT EFFECTS; SOLVENT TOLERANCE;

EID: 80054014186     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.23275     Document Type: Article
Times cited : (10)

References (36)
  • 1
    • 33846074007 scopus 로고    scopus 로고
    • Structural characterization of a β-diketone hydrolase from cyanobacterium Anabaena sp. PCC 7120 in native and product-bound forms, a coenzyme A-independent member of the crotonase superfamily
    • Bennett JP, Whittingham JL, Brzozowski AM, Leonard PM, Grogan G. 2007. Structural characterization of a β-diketone hydrolase from cyanobacterium Anabaena sp. PCC 7120 in native and product-bound forms, a coenzyme A-independent member of the crotonase superfamily. Biochemistry 46: 137-144.
    • (2007) Biochemistry , vol.46 , pp. 137-144
    • Bennett, J.P.1    Whittingham, J.L.2    Brzozowski, A.M.3    Leonard, P.M.4    Grogan, G.5
  • 2
    • 79953318587 scopus 로고    scopus 로고
    • Status of protein engineering for biocatalysts: How to design an industrially useful biocatalyst
    • Bommarius AS, Blum JK, Abrahamson MJ. 2010. Status of protein engineering for biocatalysts: How to design an industrially useful biocatalyst. Curr Opin Chem Biol 15: 1-7.
    • (2010) Curr Opin Chem Biol , vol.15 , pp. 1-7
    • Bommarius, A.S.1    Blum, J.K.2    Abrahamson, M.J.3
  • 3
    • 33847653796 scopus 로고    scopus 로고
    • An engineered mutant, L307V of phenylalanine dehydrogenase from Bacillus sphaericus: High activity and stability in organic-aqueous solvent mixtures and utility for synthesis of non-natural L-amino acids
    • Chen S, Engel PC. 2007. An engineered mutant, L307V of phenylalanine dehydrogenase from Bacillus sphaericus: High activity and stability in organic-aqueous solvent mixtures and utility for synthesis of non-natural L-amino acids. Enzyme Microb Technol 40: 1407-1411.
    • (2007) Enzyme Microb Technol , vol.40 , pp. 1407-1411
    • Chen, S.1    Engel, P.C.2
  • 4
    • 75349100918 scopus 로고    scopus 로고
    • Organic solvent-tolerant enzymes
    • Doukyu N, Ogino H. 2010. Organic solvent-tolerant enzymes. Biochem Eng J 48: 270-282.
    • (2010) Biochem Eng J , vol.48 , pp. 270-282
    • Doukyu, N.1    Ogino, H.2
  • 6
    • 80054019847 scopus 로고    scopus 로고
    • N-(3-Amino-2-hydroxy-propyl) substituted alkylamide compounds. US 2003/0109559 A1
    • Gailunas A, Tucker JA, TenBrink R, Mickelson J. 2003. N-(3-Amino-2-hydroxy-propyl) substituted alkylamide compounds. US 2003/0109559 A1.
    • (2003)
    • Gailunas, A.1    Tucker, J.A.2    TenBrink, R.3    Mickelson, J.4
  • 7
    • 21744450137 scopus 로고    scopus 로고
    • Emergent mechanistic diversity of enzyme-catalysed β-diketone cleavage
    • Grogan G. 2005. Emergent mechanistic diversity of enzyme-catalysed β-diketone cleavage. Biochem J 388: 721-730.
    • (2005) Biochem J , vol.388 , pp. 721-730
    • Grogan, G.1
  • 8
    • 0035857569 scopus 로고    scopus 로고
    • An asymmetric enzyme-catalyzed retro-Claisen reaction for the desymmetrization of cyclic β-diketones
    • Grogan G, Graf J, Jones A, Parsons S, Turner NJ, Flitsch SL. 2001a. An asymmetric enzyme-catalyzed retro-Claisen reaction for the desymmetrization of cyclic β-diketones. Angew Chem Int Ed 40: 1111-1114.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 1111-1114
    • Grogan, G.1    Graf, J.2    Jones, A.3    Parsons, S.4    Turner, N.J.5    Flitsch, S.L.6
  • 9
    • 0035918262 scopus 로고    scopus 로고
    • The desymmetrization of bicyclic β-diketones by an enzymatic retro-Claisen reaction
    • Grogan G, Roberts GA, Bougioukou D, Turner NJ, Flitsch SL. 2001b. The desymmetrization of bicyclic β-diketones by an enzymatic retro-Claisen reaction. J Biol Chem 276: 12565-12572.
    • (2001) J Biol Chem , vol.276 , pp. 12565-12572
    • Grogan, G.1    Roberts, G.A.2    Bougioukou, D.3    Turner, N.J.4    Flitsch, S.L.5
  • 10
    • 50249180217 scopus 로고    scopus 로고
    • Mechanisms and structures of crotonase superfamily enzymes-How nature controls enolate and oxyanion reactivity
    • Hamed RB, Bachelar ET, Clifton IJ, Schofield CJ. 2008. Mechanisms and structures of crotonase superfamily enzymes-How nature controls enolate and oxyanion reactivity. Cell Mol Life Sci 65: 2507-2527.
    • (2008) Cell Mol Life Sci , vol.65 , pp. 2507-2527
    • Hamed, R.B.1    Bachelar, E.T.2    Clifton, I.J.3    Schofield, C.J.4
  • 11
    • 76949088707 scopus 로고    scopus 로고
    • Carboxymethylproline synthase catalysed syntheses of functionalised N-heterocycles
    • Hamed RB, Mecinović J, Ducho C, Claridge TDW, Schofield CJ. 2010. Carboxymethylproline synthase catalysed syntheses of functionalised N-heterocycles. Chem Commun 46: 1413-1415.
    • (2010) Chem Commun , vol.46 , pp. 1413-1415
    • Hamed, R.B.1    Mecinović, J.2    Ducho, C.3    Claridge, T.D.W.4    Schofield, C.J.5
  • 14
    • 34547141829 scopus 로고    scopus 로고
    • On the resolution of chiral substrates by a retro-Claisenase enzyme: Biotransformations of heteroannular bicyclic β-diketones by 6-oxo camphor hydrolase
    • Hill CL, Hung LC, Smith DJ, Verma CS, Grogan G. 2007a. On the resolution of chiral substrates by a retro-Claisenase enzyme: Biotransformations of heteroannular bicyclic β-diketones by 6-oxo camphor hydrolase. Adv Synth Catal 349: 1353-1360.
    • (2007) Adv Synth Catal , vol.349 , pp. 1353-1360
    • Hill, C.L.1    Hung, L.C.2    Smith, D.J.3    Verma, C.S.4    Grogan, G.5
  • 15
    • 34547154816 scopus 로고    scopus 로고
    • Desymmetrisations of 1-alkylbicyclo[3.3.0]octane-2,8-diones by enzymatic retro-Claisen reaction yield optically enriched 2,3-substituted cyclopentanones
    • Hill CL, Verma CS, Grogan G. 2007b. Desymmetrisations of 1-alkylbicyclo[3.3.0]octane-2, 8-diones by enzymatic retro-Claisen reaction yield optically enriched 2, 3-substituted cyclopentanones. Adv Synth Catal 349: 916-924.
    • (2007) Adv Synth Catal , vol.349 , pp. 916-924
    • Hill, C.L.1    Verma, C.S.2    Grogan, G.3
  • 16
    • 27844563238 scopus 로고    scopus 로고
    • Biocatalysis in semi-aqueous and nearly anhydrous conditions
    • Hudson EP, Eppler RK, Clark DS. 2005. Biocatalysis in semi-aqueous and nearly anhydrous conditions. Curr Opin Biotechnol 16: 637-643.
    • (2005) Curr Opin Biotechnol , vol.16 , pp. 637-643
    • Hudson, E.P.1    Eppler, R.K.2    Clark, D.S.3
  • 17
    • 0036708692 scopus 로고    scopus 로고
    • Liquid densities and excess volumes of diisopropyl ether (DIPE)+1-butanol mixtures from 273 to 473K and pressures up to 35MPa
    • Ihmels EC, Gmehling J. 2002. Liquid densities and excess volumes of diisopropyl ether (DIPE)+1-butanol mixtures from 273 to 473K and pressures up to 35MPa. J Chem Eng Data 47: 1314-1319.
    • (2002) J Chem Eng Data , vol.47 , pp. 1314-1319
    • Ihmels, E.C.1    Gmehling, J.2
  • 18
    • 0025882622 scopus 로고
    • Denaturation capacity: A new quantitative criterion for selection of organic solvents as reaction media in biocatalysis
    • Khmelnitsky YL, Mozhaev VV, Belova AB, Sergeeva MV, Martinek K. 1991. Denaturation capacity: A new quantitative criterion for selection of organic solvents as reaction media in biocatalysis. Eur J Biochem 198: 31-41.
    • (1991) Eur J Biochem , vol.198 , pp. 31-41
    • Khmelnitsky, Y.L.1    Mozhaev, V.V.2    Belova, A.B.3    Sergeeva, M.V.4    Martinek, K.5
  • 19
    • 34548232365 scopus 로고    scopus 로고
    • Inference of macromolecular assemblies from crystalline state
    • Krissinel E, Henrick K. 2007. Inference of macromolecular assemblies from crystalline state. J Mol Biol 372: 774-797.
    • (2007) J Mol Biol , vol.372 , pp. 774-797
    • Krissinel, E.1    Henrick, K.2
  • 20
    • 84857237925 scopus 로고    scopus 로고
    • Substituted 2-mercapto-3-aminopyridines as KNCQ2/3 modulators. WO 2010/102810 A1.
    • Kühnert S, Merla B, Kless A, Bahrenberg G, Schröder W. 2010. Substituted 2-mercapto-3-aminopyridines as KNCQ2/3 modulators. WO 2010/102810 A1.
    • (2010)
    • Kühnert, S.1    Merla, B.2    Kless, A.3    Bahrenberg, G.4    Schröder, W.5
  • 21
    • 0023385987 scopus 로고
    • Rules for optimization of biocatalysis in organic solvents
    • Laane C, Boeren S, Vos K, Veeger C. 1987. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30: 81-87.
    • (1987) Biotechnol Bioeng , vol.30 , pp. 81-87
    • Laane, C.1    Boeren, S.2    Vos, K.3    Veeger, C.4
  • 22
    • 76149110500 scopus 로고    scopus 로고
    • Solvent effects on catalysis by Escherichia coli dihydrofolate reductase
    • Loveridge EJ, Tey L-H, Allemann RK. 2010. Solvent effects on catalysis by Escherichia coli dihydrofolate reductase. J Am Chem Soc 132: 1137-1143.
    • (2010) J Am Chem Soc , vol.132 , pp. 1137-1143
    • Loveridge, E.J.1    Tey, L.-H.2    Allemann, R.K.3
  • 23
    • 34250844401 scopus 로고    scopus 로고
    • Xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus performs asymmetric reduction of hydrophobic ketones in organic solvents
    • Musa MM, Ziegelmann-Fjeld KI, Vieille C, Zeikus JG, Phillips RS. 2007. Xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus performs asymmetric reduction of hydrophobic ketones in organic solvents. Angew Chem Int Ed 46: 3091-3094.
    • (2007) Angew Chem Int Ed , vol.46 , pp. 3091-3094
    • Musa, M.M.1    Ziegelmann-Fjeld, K.I.2    Vieille, C.3    Zeikus, J.G.4    Phillips, R.S.5
  • 24
    • 77954038128 scopus 로고    scopus 로고
    • Activity and enantioselectivity of the hydroxynitrile lyase MeHNL in dry organic solvents
    • Paravidino M, Sorgedrager MJ, Orru RVA, Hanefeld U. 2010. Activity and enantioselectivity of the hydroxynitrile lyase MeHNL in dry organic solvents. Chem Eur J 16: 7596-7604.
    • (2010) Chem Eur J , vol.16 , pp. 7596-7604
    • Paravidino, M.1    Sorgedrager, M.J.2    Orru, R.V.A.3    Hanefeld, U.4
  • 25
    • 33746238128 scopus 로고    scopus 로고
    • Towards a general scale of nucleophilicity?
    • Phan TB, Breugst M, Mayr H. 2006. Towards a general scale of nucleophilicity? Angew Chem Int Ed 45: 3869-3874.
    • (2006) Angew Chem Int Ed , vol.45 , pp. 3869-3874
    • Phan, T.B.1    Breugst, M.2    Mayr, H.3
  • 26
    • 78149432825 scopus 로고    scopus 로고
    • Laboratory evolution of stereoselective enzymes: A prolific source of catalyst for asymmetric reactions
    • Reetz MT. 2011. Laboratory evolution of stereoselective enzymes: A prolific source of catalyst for asymmetric reactions. Angew Chem Int Ed 50: 138-174.
    • (2011) Angew Chem Int Ed , vol.50 , pp. 138-174
    • Reetz, M.T.1
  • 27
    • 78149450306 scopus 로고    scopus 로고
    • Increasing the stability of an enzyme toward hostile organic solvents by directed evolution based on iterative saturation mutagenesis using the B-FIT method
    • Reetz MT, Soni P, Fernández L, Gumulya Y, Carballeira JD. 2010. Increasing the stability of an enzyme toward hostile organic solvents by directed evolution based on iterative saturation mutagenesis using the B-FIT method. Chem Commun 46: 8657-8658.
    • (2010) Chem Commun , vol.46 , pp. 8657-8658
    • Reetz, M.T.1    Soni, P.2    Fernández, L.3    Gumulya, Y.4    Carballeira, J.D.5
  • 30
    • 37349126715 scopus 로고    scopus 로고
    • Enzyme activation for organic solvents made easy
    • Serdakowski AL, Dordick JS. 2008. Enzyme activation for organic solvents made easy. Trends Biotechnol 26: 48-54.
    • (2008) Trends Biotechnol , vol.26 , pp. 48-54
    • Serdakowski, A.L.1    Dordick, J.S.2
  • 31
    • 0042808596 scopus 로고    scopus 로고
    • Is logP a convenient criterion to guide the choice of solvents for biphasic enzymatic reactions?
    • Villela Filho M, Stillger T, Müller M, Liese A, Wandrey C. 2003. Is logP a convenient criterion to guide the choice of solvents for biphasic enzymatic reactions? Angew Chem Int Ed 42: 2993-2996.
    • (2003) Angew Chem Int Ed , vol.42 , pp. 2993-2996
    • Villela Filho, M.1    Stillger, T.2    Müller, M.3    Liese, A.4    Wandrey, C.5
  • 32
    • 79251559401 scopus 로고    scopus 로고
    • Immobilization of Thermoanaerobium brockii alcohol dehydrogenase on SBA-15
    • Vittorini M, Dumitriu E, Barletta G, Secundo F. 2011. Immobilization of Thermoanaerobium brockii alcohol dehydrogenase on SBA-15. Bioprocess Biosyst Eng 34: 247-251.
    • (2011) Bioprocess Biosyst Eng , vol.34 , pp. 247-251
    • Vittorini, M.1    Dumitriu, E.2    Barletta, G.3    Secundo, F.4
  • 35
    • 78650392878 scopus 로고    scopus 로고
    • Drying of organic solvents: Quantitative evaluation of the efficiency of several desiccants
    • Williams DBG, Lawton M. 2010. Drying of organic solvents: Quantitative evaluation of the efficiency of several desiccants. J Org Chem 75: 8351-8354.
    • (2010) J Org Chem , vol.75 , pp. 8351-8354
    • Williams, D.B.G.1    Lawton, M.2
  • 36
    • 0842278671 scopus 로고    scopus 로고
    • Laboratory evolution of cytochrome P450 BM-3 monooxygenase for organic cosolvents
    • Wong TS, Arnold FH, Schwaneberg U. 2004. Laboratory evolution of cytochrome P450 BM-3 monooxygenase for organic cosolvents. Biotechnol Bioeng 85: 351-358.
    • (2004) Biotechnol Bioeng , vol.85 , pp. 351-358
    • Wong, T.S.1    Arnold, F.H.2    Schwaneberg, U.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.