Epoxide hydrolase enantioconvergent

Furstoss et al. have reported their studies on the use of an epoxide hydrolase with four styrene oxide derivatives (Figure 5.26) [39]. The (R)-diol (43) was obtained in 91% ee at 100% conversion from racemic (42), demonstrating an enantioconvergent... 

Figure 5.25 Enantioconvergent hydrolysis of epoxides (35) to the corresponding diols (36) using mung bean epoxide hydrolase.

Lee, E.Y. and Shuler, M.L. (2007) Molecular engineering of epoxide hydrolase and its application to asymmetric and enantioconvergent hydrolysis. Biotechnology and Bioengineering, 98, 318-327. 

Epoxide hydrolases from mung bean Enantioconvergent biohydrolysis X= H, NOj.CI... 

Scheme 2.3 Enantioconvergent hydrolysis of styrene epoxides by Vigna radiata epoxide hydrolases.

Another example of an enantioconvergent transformation of racemic epoxides was reported by Faber and coworkers who employed a chemoenzymatic approach for the synthesis of optically enriched diols. They used an (S)-selective epoxide hydrolase from Nocardia sp. in connection with an add catalyzed hydrolytic step to convergently prepare (S)-diols 41 in good to excellent yields (71-98%) with enantiomeric excess values up to 99% (Scheme 9.13) [75]. 

R. V.A. Orm, W. Kroutil, K. Faber, Deracemization of (+/-)-2,2-disubstituted epoxides via enantioconvergent chemoenzymatic hydrolysis using Nocardia EHl epoxide hydrolase and sulfuric acid. Tetrahedron Lett. 38 (1997) 1753-1754. 

Monteide, M.I., Lombard, M., Archelas, A., Cronin, A., Arand, M. and Furstoss, R. (2004) Enzymatic transformations. Part 58 Enantioconvergent biohydrolysis of styrene oxide derivatives catalysed by the Solanum tuberosum epoxide hydrolase. Tetrahedron Asymmetry, 15,2801-2805. 

Kotik, M., Archelas, A., FamSrova, V., Oubrechtova, P and Kfen, V. (2011) Laboratory evolution of an epoxide hydrolase— towards an enantioconvergent biocatalyst. /. BiotechnoL, 156,1-10. 

Kotik, M., Zhao, W., lacazio, G. and Archelas, A. (2013) Directed evolution of metagenome-derived epoxide hydrolase for improved enantioselectivity and enantioconvergence. /. Mol Catal. B Enzym., 91,44-51. 

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. 

Gao, L., Lee, J., Chen, W. and Wood, T.K. (2006) Enantioconvergent production of (R)-l-phenyl-l,2-ethanediol from styrene oxide by combining the Solatium tuberosum and an evolved Agrobacterium radiobacter ADI epoxide hydrolases. Biotechnol. Bioeng., 94, 522-529. 

Hwang, S., Choi, C.Y. and Lee, E.Y. (2008) Enantioconvergent bioconversion of p-chlo-rostyrene oxide to (R)-p-chlorophenyl-l,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus. Biotechnol. Lett., 30,1219-1225. 

Kroutil, W., Mischitz, M. and Faber, K. (1997) Deracemisation of ( )-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases kinetics of an enantioconvergent process. /. Chem. Soc. Perkin Trans. 1, 3629-3636. 

Steinreiber, A., Hellstrom, H., Mayer, S.R, Orru, R.V.A. and Faber, K. (2001) Chemoenzymatic enantioconvergent S5mthesis of C4-building blocks containing a fully substituted chiral carbon center using bacterial epoxide hydrolases. Synlett, 111-113. 

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