Concepedia

Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols

Dongliang Chang, Zunsheng Wang, M. F. Heringa, Renato Wirthner, Bernard Witholt, Zhi Li

Chemical Communications · 2003 · 38 citations · 14 references

DOI

Concepts

Abstract

Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase.

References

14

The X-ray Structure of Epoxide Hydrolase from Agrobacterium radiobacter AD1

Marco Nardini, I.S. Ridder, H.J. Rozeboom et al. · Journal of Biological Chemistry · 1999 · 177 citations · Full text

, , +17

Role of the arene oxide-oxepin system in the metabolism of aromatic substrates. IV. Stereochemical considerations of dihydrodiol formation and dehyrogenation

Donald M. Jerina, Herman Ziffer, John W. Daly · Journal of the American Chemical Society · 1970 · 132 citations

, , +14

Epoxide hydrolases as asymmetric catalysts

Ian Archer · Tetrahedron · 1997 · 109 citations

, , +14

Microbiological transformations. Part 45: A green chemistry preparative scale synthesis of enantiopure building blocks of Eliprodil: elaboration of a high substrate concentration epoxide hydrolase-catalyzed hydrolytic kinetic resolution process

Kelath Murali Manoj, Alain Archelas, J. Baratti et al. · Tetrahedron · 2001 · 95 citations

, , +17

Preparation of (<i>R</i>)- and (<i>S</i>)-<i>N</i>-Protected 3-Hydroxypyrrolidines by Hydroxylation with <i>Sphingomonas</i> sp. HXN-200, a Highly Active, Regio- and Stereoselective, and Easy to Handle Biocatalyst

Zhi Li, Hans-Jürgen Feiten, Dongliang Chang et al. · The Journal of Organic Chemistry · 2001 · 78 citations

, , +9