Abstract
A novel epoxide hydrolase (EHase) from polycyclic aromatic hydrocarbon (PAH)-degrading bacteria was identified and characterized. EHase activity was identified in four strains of PAH-degrading bacteria isolated from commercial gasoline and oil-contaminated sediment based on their growth on styrene oxide and its derivatives, such as 2,3- and 4-chlorostyrene oxides, as a sole carbon source. Gordonia sp. H37 exhibited high enantioselective hydrolysis activity for 4-chlorostyrene oxide with an enantiomeric ratio of 27. Gordonia sp. H37 preferentially hydrolyzed the (R)-enantiomer of styrene oxide derivatives resulting in the preparation of a (S)-enantiomer with enantiomeric excess greater than 99.9 %. The enantioselective EHase activity was identified and characterized in various PAH-degrading bacteria, and whole cell Gordonia sp. H37 was employed as a biocatalyst for preparing enantiopure (S)-styrene oxide derivatives.
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References
Archelas A, Furstoss R (1997) Synthesis of enantiopure epoxides through biocatalytic approaches. Annu Rev Microbiol 51:491–525
Archelas A, Furstoss R (2001) Synthetic applications of epoxide hydrolases. Curr Opin Chem Biol 5:112–119
Besse P, Veschambre H (1994) Chemical and biological synthesis of chiral epoxides. Tetrahedron 50:8885–8892
Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104:7294–7299
Choi SH, Kim HS, Lee EY (2009) Comparative homology modeling-inspired protein engineering for improvement of catalytic activity of Mugil cephalus epoxide hydrolase. Biotechnol Lett 31:1617–1624
de Vries EJ, Janssen DB (2003) Biocatalytic conversion of epoxides. Curr Opin Biotechnol 14:414–420
Grogan G, Roberts SM, Willetts AJ (1996) Novel aliphatic epoxide hydrolase activities from dematiaceous fungi. FEMS Microbiol Lett 141:239–243
Hwang Y-O, Kang SG, Woo J-H, Kwon KK, Sato T, Lee EY, Han MS, Kim S-J (2008) Screening enantioselective epoxide hydrolase activities from marine microorganisms: detection of activities in Erythrobacter spp. Marine Biotechnol 10:366–373
Hwang S, Choi CY, Lee EY (2010) Bio- and chemo-catalytic preparation of chiral epoxides. J Ind Eng Chem 16:1–6
Jia X, Wang Z, Li Z (2008) Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200. Tetrahedron: Asymmetry 19:407–415
Karboune S, Archelas A, Baratti JC (2010) Free and immobilized Aspergillus niger epoxide hydrolase-catalyzed hydrolytic kinetic resolution of racemic p-chlorostyrene oxide in a neat organic solvent medium. Process Biochem 45:210–215
Kasai N, Suzuki T, Furukawa Y (1998) Chiral C3 epoxides and halohydrins: their preparation and synthetic application. J Mol Catal B Enzym 4:237–252
Kim HS, Lee OK, Hwang S, Kim BJ, Lee EY (2008) Biosynthesis of (R)-phenyl-1,2-ethanediol from racemic styrene oxide by using bacterial and marine fish epoxide hydrolases. Biotechnol Lett 30:127–133
Kloosterman M, Elferink VHM, van Iersel J, Roskam JH, Meijer EM, Hulshof LA, Sheldon RA (1988) Lipase in the preparation of β-blockers. Trends Biotechnol 6:251–256
Kwon T-H, Kim J-T, Kim J-S (2010) Application of a modified sublimation method to screen for PAH-degrading microorganisms. Korean J Microbiol 46:109–111
Lee EY (2008) Epoxide hydrolase-mediated enantioconvergent bioconversions to prepare chiral epoxides and alcohols. Biotechnol Lett 30:1509–1514
Orru RV, Faber K (1999) Stereoselectivities of microbial epoxide hydrolases. Curr Opin Chem Biol 3:16–21
Straathof AJJ, Jongejan JA (1997) The enantiomeric ratio: origin, determination and prediction. Enzym Microb Technol 21:559–571
Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN (1997) Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. Science 277:936–938
van Loo B, Kingma J, Arand M, Wubbolts MG, Janssen DB (2006) Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis. Appl Environ Microbiol 72:2905–2917
Weijers CAGM, de Bont JAM (1999) Epoxide hydrolases from yeasts and other sources: versatile tools in biocatalysis. J Mol Catal B Enzym 6:199–214
Woo J-H, Hwang O-K, Kang SG, Lee HS, Cho J, Kim S-J (2007) Cloning and characterization of three novel epoxide hydrolases from a marine bacterium, Erythrobacter litoralis HTCC2594. Appl Microbiol Biotechnol 76:365–375
Woo J-H, Kang JH, Kang SG, Hwang O-K, Kim S-J (2009) Cloning and characterization of an epoxide hydrolase from Novosphingovium aromaticivorans. Appl Microbiol Biotechnol 82:873–881
Woo J-H, Hwang O-K, Kang JH, Kim S-J, Kang SG (2010a) Enantioselective hydrolysis of racemic epichlorohydrin using an epoxide hydrolase from Novosphingobium aromaticivorans. J Biosci Bioeng 110:295–297
Woo J-H, Kang JH, Hwang O-K, Cho J, Kim S-J, Kang SG (2010b) Biocatalytic resolution of glycidyl phenyl ether using a novel epoxide hydrolase from a marine bacterium, Rhodobacterales bacterium HTCC2654. J Biosci Bioeng 109:539–544
Yeate CA, Krie HM, Breytenbac JC (2007) Hydroxypropyl-beta-cyclodextrin induced complexation for the biocatalytic resolution of a poorly soluble epoxide. Enzym Microb Technol 40:228–235
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This work supported by GIMB in-House R&D Program and the Marine and Extreme Genome Research Centre Program, Ministry of Land, Transport and Maritime Affairs, Republic of Korea.
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Woo, JH., Kwon, TH., Kim, JT. et al. Identification and characterization of epoxide hydrolase activity of polycyclic aromatic hydrocarbon-degrading bacteria for biocatalytic resolution of racemic styrene oxide and styrene oxide derivatives. Biotechnol Lett 35, 599–606 (2013). https://doi.org/10.1007/s10529-012-1114-1
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DOI: https://doi.org/10.1007/s10529-012-1114-1