Journal
MOLECULES
Volume 21, Issue 6, Pages -Publisher
MDPI
DOI: 10.3390/molecules21060767
Keywords
lipase; immobilization; covalent attachment; kinetic resolution; thermal stabilization; continuous-flow reactor
Funding
- New Szechenyi Development Plan (Development of quality oriented and harmonized R+D+I strategy and functional model at BME project) [TAMOP-4.2.1/B-09/1/KMR-2010-0002]
- Gedeon Richter pharmaceutical company
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An efficient and easy-to-perform method was developed for immobilization of CaLB on mesoporous aminoalkyl polymer supports by bisepoxide activation. Polyacrylate resins (100-300 mu m; similar to 50 nm pores) with different aminoalkyl functional groups (ethylamine: EA and hexylamine: HA) were modified with bisepoxides differing in the length, rigidity and hydrophobicity of the units linking the two epoxy functions. After immobilization, the different CaLB preparations were evaluated using the lipase-catalyzed kinetic resolution (KR) of racemic 1-phenylethanol (rac-1) in batch mode and in a continuous-flow reactor as well. Catalytic activity, enantiomer selectivity, recyclability, and the mechanical and long-term stability of CaLB immobilized on the various supports were tested. The most active CaLB preparation (on HA-resin activated with 1,6-hexanediol diglycidyl ether-HDGE) retained 90% of its initial activity after 13 consecutive reaction cycles or after 12 month of storage at 4 degrees C. The specific rate (r(flow)), enantiomer selectivity (E) and enantiomeric excess (ee) achievable with the best immobilized CaLB preparations were studied as a function of temperature in kinetic resolution of rac-1 performed in continuous-flow packed-bed bioreactors. The optimum temperature of the most active HA-HDGE CaLB in continuous-flow mode was 60 degrees C. Although CaLB immobilized on the glycerol diglycidyl ether (GDGE)-activated EA-resin was less active and less selective, a much higher optimum temperature (80 degrees C) was observed with this form in continuous-flow mode KR of rac-1.
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