Epoxide hydrolases immobilization

Devi, A.V., Lahari, G., Swamalatha, L. and Fadnavis, N.W. (2008) Gelozymes in organic s5mthesis. Part IV resolution of glycidate esters with crude mung bean (Phaseolus radia-tus) epoxide hydrolase immobilized in gelatin matrix. Tetrahedron Asymmetry, 19, 1139-1144. 

Petri, A., Marconcini, P. and Salvadori, P. (2005) Efficient immobilization of epoxide hydrolase onto silica gel and use in the enantioselective hydrolysis of racemic para-nitrostyrene oxide. J. Mol. Catal. B Enzymatic, 32, 219. 

In biocatalysis, hydrolases are the most important class of enzymes for carrying out enzymatic resolutions. Many hydrolases, such as esterases, lipases, epoxide hydrolases, proteases, peptidases, acylases, and amidases, are commercially available a substantial number of them are bulk enzymes [87]. Resting-cell systems, if they are not immobilized, are used in diluted suspensions and could be handled as quasi-homogeneous catalysts. 

When racemic aryl glycidyl ethers were subjected to aminolysis in aqueous buffer catalyzed by hepatic microsomal epoxide hydrolase from rat, the corresponding (S)-configurated amino-alcohols were obtained in 51-88% ee 131. On the other hand, when azide was employed as nucleophile for the asymmetric opening of 2-methyl-1,2-epoxyheptane in the presence of an immobilized crude enzyme preparation derived from Rhodococcus sp., which contains an epoxide hydrolase activity, the reaction revealed a complex picture 1321. The (S)-epoxide from the racemate was hydrolyzed (as in the absence of azide), and the less readily accepted (i )-enantiomer was transformed into the corresponding azido-alcohol (ee >60%). Although at present only speculations can be made about the actual mechanism of both the aminolysis and azidolysis reaction, in both cases it was proven that the reaction was catalyzed by a protein and that no reaction was observed in the absence of biocatalyst... 

SP 361 SP 409 Immobilized enzyme mixture from Rhodococcus sp. containing nitrilase, nitril hydratase,esterase, epoxide hydrolase and amidase activity discontinued... 

Immobilized coli cells expressing epoxide hydrolase activity... 

Grulich, M., Marsalek, J., Kyslik, P, Stepanek, V. and Kotik, M. (2011) Production, enrichment and immobilization of a metagenome-derived epoxide hydrolase. Process Biochem., 46,526-532. 

Mateo, C., Femandez-Lafuente, R., Archelas, A., Guisan, J.M. and Furstoss, R. (2007) Preparation of a very stable immobilized Solanum tuberosum epoxide hydrolase. Tetrahedron Asymmetry, 18,1233-1238. 

Karboune, S., Archelas, A., Fiustoss, R. and Baratti, J. (2005) Immobilization of the Solanum tuberosum epoxide hydrolase and its ap>plication in an enantioconvergent process. Biocatal. Biotransformation, 23,397—105. 

Yildirim, D., Tiikel, S.S., Alptekin, O. and Alagoz, D. (2013) Immobilized Aspergillus niger epoxide hydrolases cost-effective biocatalysts for the preparation of enantiopure styrene oxide, propylene oxide and epichlorohydrin. /. Mol. Catal. B Enzym., 88, 84r-90. 

Karboune, S., Archelas, A. and Baratti, J.C. (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., 45,210-216. 

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