Lipase B from Candida antarctica Immobilized on Epoxy-functionalized Hollow Silica Microspheres: Efficient Biocatalysts for Enantiomer Selective Acylation of Alcohols and Amines

  • Márk Oláh Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Műegyetem rkp. 3, Hungary
  • Szandra Suba Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Műegyetem rkp. 3, Hungary
  • Zoltán Boros SynBiocat LLC., H-1172 Budapest, Szilasliget u. 3, Hungary
  • Péter Kovács Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Magyar tudósok kt. 2, Hungary
  • Mathilde Gosselin Materium Innovations INC., Boulevard Industriel 790, J2G 9J5 Granby, Canada
  • Charles Gaudreault Materium Innovations INC., Boulevard Industriel 790, J2G 9J5 Granby, Canada
  • Gábor Hornyánszky Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1111 Budapest, Műegyetem rkp. 3, Hungary; SynBiocat LLC., H-1172 Budapest, Szilasliget u. 3, Hungary

Abstract

Hollow silica microspheres with promising physical properties (MAT540TM) as support for enzyme immobilization and biocatalyst were investigated in this study. The amine-functionalized MAT540TM was activated by six bisepoxides inclosing different spacers and used as epoxy-functionalized carrier for immobilization of lipase B from Candida antarctica (CaLB). The novel, covalently fixed CaLB biocatalysts were compared in kinetic resolution (KR) of racemic 1-phenyethanol rac-1 and five racemic amines rac-3a-e using shaken flasks and continuous-flow packed-bed microreactors. Mechanic stability, re-usability and the effect of temperature (0–90 °C) on productivity and enantiomer selectivity of the covalently immobilized CaLB were investigated. The best performing CaLB biocatalyst showed good mechanic stability after 24 h operation time in continuous-flow mode at 60 °C and provided in KRs of racemic 1-phenyethanol rac-1 with vinyl acetate and of five racemic amines with isopropyl 2-ethoxyacetate as acylating agent the non-reacted (S)-alcohol [(S)-1] or (S)-amines [(S)-3a-e] and the forming (R)-ester [(R)-2] or (R)-amide [(R)-4a-e] in good yields with high enantiomeric excess (ee > 99 %, for all).

Keywords: alcohol, amine, biocatalysis, continuous-flow mode, kinetic resolution
Published online
2018-10-01
How to Cite
Oláh, M., Suba, S., Boros, Z., Kovács, P., Gosselin, M., Gaudreault, C. and Hornyánszky, G. (2018) “Lipase B from Candida antarctica Immobilized on Epoxy-functionalized Hollow Silica Microspheres: Efficient Biocatalysts for Enantiomer Selective Acylation of Alcohols and Amines”, Periodica Polytechnica Chemical Engineering, 62(4), pp. 519–532. doi: https://doi.org/10.3311/PPch.12517.
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Articles