Conventional enantioselective preparative chromatographic separation using columns packed with chiral stationary phase is characterized by a 50% yield constraint. Racemization of the undesired enantiomer and recycling the formed mixture is an attractive option to tackle this limit. To implement this concept, potential is seen in particular in applying enzymes immobilized in a second fixed bed. However, the identification of suitable operating conditions and the direct connection of a chromatographic column and an enzymatic reactor is not trivial. The paper presents results of an experimental study applying jointly a batch-wise operated chiral Chirobiotic T column to resolve the two enantiomers of mandelic acid (MA) and a mandelate racemase immobilized on Eupergit CM. The general concept could be successfully demonstrated over several cycles focusing on the provision of (S)-MA. A mathematical model was developed in order to illustrate essential process features and to quantitatively describe the coupled separation and racemization processes. The key ingredients of this model, namely, the adsorption isotherms of the two enantiomers on the chiral column and the rate of racemization in the enzymatic reactor, were determined experimentally. The potential of applying the model for further process optimization and generalization is indicated.
Combination of Enantioselective Preparative Chromatography and Racemization: Experimental Demonstration and Model-Based Process Optimization
link https://pubs.acs.org/doi/10.1021/acs.oprd.8b00254
Dr. Katarzyna Wrzosek
Phone:+49 391 6110 321
Max-Planck Institute for Dynamics of Complex Technical System, Physical and Chemical Foundations of Process Engineering, 39106 Magdeburg, Germany
*E-mail: wrzosek@mpi-magdeburg.mpg.de.
M. Sc. Isabel Harriehausen
Phone:+49 391 6110 447 harriehausen@mpi-magdeburg.mpg.de
Prof. Dr.-Ing. Andreas Seidel-Morgenstern
Phone:+49 391 6110 401
Magdeburg, Germany
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///////////////enantioselective chromatography, enzymatic reactor, equilibrium dispersion model, mandelate racemase, racemization
