Pseudomonas cepacia lipase immobilized on Zn₂Al layered double hydroxides: Evaluation of different methods of immobilization for the kinetic resolution of (R,S)-1-phenylethanol

Abstract

The present work deals with the preparation and characterization of Zn₂Al layered double hydroxides (LDHs) intercalated with chloride and dodecyl sulfate ions and their use as supports for the immobilization of Pseudomonas cepacia lipase (LipPS). LipPS was immobilized on LDH by adsorption, in situ entrapment and delamination entrapment methods. The performance of free and immobilized LipPS in the transesterification of (R,S)-1-phenylethanol was compared. The immobilized derivatives prepared by adsorption gave the highest conversions (c = 50%), with an enantiomeric excess of the product (ee_p) greater than 99% and a high enantiomeric ratio (E > 200). For immobilization by in situ entrapment (coprecipitation), a conversion of 31.5% and E > 200 were obtained. For immobilization by delamination entrapment, a conversion of 36% and E= 155 were obtained. Although the best results were obtained by adsorption, these results show that the delamination entrapment method can also be used to prepare bioinorganic-enzyme materials based on LDH. Our work therefore increases the range of methods that can be used to immobilize lipases for use in the production of optically pure secondary alcohols.

Graphical Abstract

Keywords:

• Lipases
• layered double hydroxide
• immobilization
• kinetic resolution
• secondary alcohols

Acknowledgements

The authors thank Centro de Microscopia Eletrônica – CME/UFPR for the SEM and EDS measurements, Centro de Estudo do Mar – CEM/UFPR for the CHN analysis and Central Analítica da Química – UFPR for the TGA analysis and David Mitchell for the help with the English expression.

Author contributions

Lilian FM do Amaral: experimental work and writing – original draft; Cristiane Pilissão and Nadia Krieger: conceptualization, writing – review and editing. Fernando Wypych: conceptualization, writing – review and editing, supervision.

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Funding

Research scholarships were granted to F. Wypych and N. Krieger, by CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico), a Brazilian government agency for the advancement of science and technology, and to L.F.M. Amaral by CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), a Brazilian government agency for the development of personnel in higher education. Grants were given by CNPq [F. Wypych: 300988/2019-2] and FINEP (Financiadora de Estudos e Projetos). The Postgraduate Program in Chemistry of the Federal University of Paraná is financed by CAP ES (Finance Code 001).