Tailoring the spacer arm for covalent immobilization of Candida antarctica lipase B - Thermal stabilization by bisepoxide-activated aminoalkyl resins in continuous-flow reactors

Emese Abaházi, Dávid Lestál, Zoltán Boros, L. Poppe

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

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 μm; ∼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°C. The specific rate (rflow), 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°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°C) was observed with this form in continuous-flow mode KR of rac-1.

Original languageEnglish
Article number767
JournalMolecules
Volume21
Issue number6
DOIs
Publication statusPublished - Jun 1 2016

Fingerprint

Antarctic regions
immobilization
Immobilization
spacers
resins
1,6-hexanediol diglycidyl ether
Enantiomers
Resins
Stabilization
Hot Temperature
stabilization
reactors
Kinetics
Temperature
enantiomers
Glyceryl Ethers
preparation
ethers
kinetics
Catalyst selectivity

Keywords

  • Continuous-flow reactor
  • Covalent attachment
  • Immobilization
  • Kinetic resolution
  • Lipase
  • Thermal stabilization

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tailoring the spacer arm for covalent immobilization of Candida antarctica lipase B - Thermal stabilization by bisepoxide-activated aminoalkyl resins in continuous-flow reactors. / Abaházi, Emese; Lestál, Dávid; Boros, Zoltán; Poppe, L.

In: Molecules, Vol. 21, No. 6, 767, 01.06.2016.

Research output: Contribution to journalArticle

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abstract = "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 μm; ∼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°C. The specific rate (rflow), 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°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°C) was observed with this form in continuous-flow mode KR of rac-1.",
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