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Effect of mass transfer limitations on the enzymatic kinetic resolution of epoxides in a two‐liquid‐phase system
Author(s) -
Baldascini Helen,
Ganzeveld Klaassien J.,
Janssen Dick B.,
Beenackers Antonie A. C. M.
Publication year - 2001
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/1097-0290(20010405)73:1<44::aid-bit1035>3.0.co;2-c
Subject(s) - kinetic resolution , chemistry , epoxide , yield (engineering) , epoxide hydrolase , styrene , styrene oxide , aqueous two phase system , octane , aqueous solution , organic chemistry , mass transfer , chromatography , enzyme , enantioselective synthesis , materials science , catalysis , polymer , copolymer , metallurgy , microsome
Optically active epoxides can be obtained by kinetic resolution of racemic mixtures using enantioselective epoxide hydrolases. To increase the productivity of the conversion of sparingly aqueous soluble epoxides, we investigated the use of a two‐phase aqueous/organic system. A kinetic model which takes into account interphase mass transfer, enzymatic reaction, and enzyme inactivation was developed to describe epoxide conversion in the system by the epoxide hydrolase from Agrobacterium radiobacter. A Lewis cell was used to determine model parameters and results from resolutions carried out in the Lewis cell were compared to model predictions to validate the model. It was found that n‐octane is a biocompatible immiscible solvent suitable for use as the organic phase. Good agreement between the model predictions and experimental data was found when the enzyme inactivation rate was fitted. Simulations showed that mass transfer limitations have to be avoided in order to maximize the yield of enantiomerically pure epoxide. Resolution of a 39 g/L solution of racemic styrene oxide in octane was successfully carried out in an emulsion batch reactor to obtain (S)‐styrene oxide in high enantiomeric excess (>95% e.e.) with a yield of 30%. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng 73:44–54, 2001.