<abstract xmlns="http://www.w3.org/1999/xhtml"><p>The enantioselective resolution of racemic styrene oxide (<italic>rac</italic>-SO) to (<italic>R</italic>)-SO by whole cells of a recombinant <italic>Escherichia coli</italic> expressing epoxide hydrolase (EH) activity in aqueous and biphasic system were studied. Some parameters that may alter this bio-resolution, such as the concentration of recombinant cell, substrate and product were evaluated. The effect of the addition of different additives on the course of <italic>rac</italic>-SO biotransformation was also investigated. The results showed that the yield and the enantiomeric excess (<italic>ee</italic>) of (<italic>R</italic>)-SO were dependent on these variables. When the kinetic resolution was conducted with 350 mM of <italic>rac</italic>-SO, enantiopure (<italic>R</italic>)-SO with high (≥99%) <italic>ee</italic> was obtained with a yield of 38.2% yield at 12.2 h in the presence of 10% (v/v) Tween 80. An isooctane/aqueous system was developed to overcome the adverse factors in the aqueous phase, resulting in an improvement of yield from 38.2% to 42.9%. The results will provide a useful guidance for further application of this enzyme in the biocatalytic production of chiral synthons.</p></abstract>

The enantioselective resolution of racemic styrene oxide (rac-SO) to (R)-SO by whole cells of a recombinant Escherichia coli expressing epoxide hydrolase (EH) activity in aqueous and biphasic system were studied. Some parameters that may alter this bio-resolution, such as the concentration of recombinant cell, substrate and product were evaluated. The effect of the addition of different additives on the course of rac-SO biotransformation was also investigated. The results showed that the yield and the enantiomeric excess (ee) of (R)-SO were dependent on these variables. When the kinetic resolution was conducted with 350 mM of rac-SO, enantiopure (R)-SO with high (≥99%) ee was obtained with a yield of 38.2% yield at 12.2 h in the presence of 10% (v/v) Tween 80. An isooctane/aqueous system was developed to overcome the adverse factors in the aqueous phase, resulting in an improvement of yield from 38.2% to 42.9%. The results will provide a useful guidance for further application of this enzyme in the biocatalytic production of chiral synthons.

Production of (<italic>R</italic>)-styrene oxide by recombinant whole-cell biocatalyst in aqueous and biphasic system

School of Marine and Bioengineering, Yancheng Institute of Technology

Polish Journal of Chemical Technology

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Production of ()-styrene oxide by recombinant whole-cell biocatalyst in aqueous and biphasic system

The enantioselective resolution of racemic styrene oxide (rac-SO) to (R)-SO by whole cells of a recombinant Escherichia coli expressing epoxide hydrolase (EH)...

Production of (R)-styrene oxide by recombinant whole-cell biocatalyst in aqueous and biphasic system

Published Online: Jul 25, 2018

Page range: 54 - 60

DOI: https://doi.org/10.2478/pjct-2018-0023

Keywords
Kinetic resolution, Epoxide hydrolase, Enantioselectivity, ()-styrene oxide

© 2018 Feng Xue et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Production of (R)-styrene oxide by recombinant whole-cell biocatalyst in aqueous and biphasic system

Published Online: Jul 25, 2018

Page range: 54 - 60

DOI: https://doi.org/10.2478/pjct-2018-0023

KeywordsKinetic resolution, Epoxide hydrolase, Enantioselectivity, ()-styrene oxide

© 2018 Feng Xue et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Keywords
Kinetic resolution, Epoxide hydrolase, Enantioselectivity, ()-styrene oxide