4.5 Article

Flow synthesis of phenylserine using threonine aldolase immobilized on Eupergit support

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 2168-2179

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.254

Keywords

Eupergit; flow chemistry; immobilized enzyme; threonine aldolase

Funding

  1. ProAChim project (ERA IB) [035581]

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Threonine aldolase (TA) from Thermotoga maritima was immobilized on an Eupergit support by both a direct and an indirect method. The incubation time for the direct immobilization method was optimized for the highest amount of enzyme on the support. By introducing the immobilized TA in a packed-bed microreactor, a flow synthesis of phenylserine was developed, and the effects of temperature and residence time were studied in particular. Calculations of the Damkohler number revealed that no mass transfer limitations are given in the micro-interstices of the packed bed. The yield does not exceed 40% and can be rationalized by the natural equilibrium as well as product inhibition which was experimentally proven. The flow synthesis with the immobilized enzyme was compared with the corresponding transformation conducted with the free enzyme. The product yield was further improved by operating under slug flow conditions which is related to the very short residence time distribution. In all cases 20% diastereomeric excess (de) and 99% enantiomeric excess (ee) were observed. A continuous run of the reactant solution was carried out for 10 hours in order to check enzyme stability at higher temperature. Stable operation was achieved at 20 minute residence time. Finally, the productivity of the reactor was calculated, extrapolated to parallel run units, and compared with data collected previously.

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