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Novel nanohybrid biocatalyst: application in the kinetic resolution of secondary alcohols

  • Biomaterials
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Abstract

In this work, a nanohybrid material was developed and used for the first time to the kinetic resolution of secondary alcohols as rac-indanol, rac-1-phenylethanol (rac-1), rac-1-(3-bromophenyl)-1-ethanol (rac-2) and rac-1-(3-methylphenyl)-1-ethanol (rac-3). Chiral indanol is used as a precursor intermediate for the synthesis of enantiomeric drugs, such as (+)-Indatraline, Irindalone, Indinavir, (+)-Sertraline and Rasagiline mesylate. Chiral 1-phenylethanol is used as an ophthalmic preservative, a solvatochromic dye and an inhibitor of cholesterol absorption and as a mild floral fragrance. For this purpose, the ultrasound irradiation was used to couple APTES on the superparamagnetic nanoparticles surface. Then, the system was activated with glutaraldehyde and used as a support for immobilization of lipase from Pseudomonas fluorescens. Thermal stability analysis was performed in buffer and hexane, showing an excellent stability in buffer solution at 60 °C, holding 72% of the initial activity, even after 7 h. In hexane (40 °C), the immobilized enzyme retained 100% of activity with 693 min of half-life time at 50 °C. The high thermal stability is mainly related to the covalent bonding between enzymes and support. Immobilized lipase on magnetic support proved to be a robust biocatalyst in the kinetic resolution, leading to (S)-indanol with high selectivity (e.e. > 99%, E > 200) in 1.75 h at 50 °C, being reused five times without significant loss of the activity and selectivity. The kinetic resolution of rac-1, via acetylation reaction, catalyzed by lipase from Pseudomonas fluorescens immobilized on magnetic support, led to (R)-acetate with enantiomeric excess > 99% and to the remaining (S)-alcohol with enantiomeric excess of 94%, conversion of 49% and E > 200, after 48 h of reaction at 40 °C. Under the same reactions conditions, rac-2 and rac-3 were slightly less reactive, since the corresponding (R)-acetates were obtained with conversion values of 44%, but with high enantioselectivity (enantiomeric excesses > 99% and E values > 200). These results correspond to an important step in heterogeneous catalysis due to the ability to obtain important precursors for the synthesis of enantiomerically pure chiral drugs and other bioactive substances.

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Acknowledgements

We gratefully acknowledge the financial support of Brazilian Agencies for Scientific and Technological Development CAPES, Funcap (PNE-0112-00048.01.00/16) and CNPq (408790/2016-4). The authors thank the Laboratório de Raios X and Laboratório de Produtos e Tecnologia de Processos (LPT) of the Universidade Federal do Ceará for the experiments and analyses. We also acknowledge Brazilian Nanotechnology National Laboratory (LNNano) for the access to electron microscopy facilities.

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Authors and Affiliations

  1. Grupo de Química de Materiais Avançados (GQMAT) - Departamento de Química Analítica e Físico-Química, Universidade Federal do Ceará - UFC, Campus do Pici, CP 12100, Fortaleza, CE, 60451-970, Brazil

    W. S. Galvão & P. B. A. Fechine

  2. Departamento de Engenharia Química, Universidade Federal do Ceará, Campus do Pici, Fortaleza, CE, 60455-760, Brazil

    B. B. Pinheiro & L. R. B. Golçalves

  3. Departamento de Química Orgânica e Inorgânica, Laboratório de Biotecnologia e Síntese Orgânica (LABS), Universidade Federal do Ceará, Campus do Pici, Caixa Postal 6044, Fortaleza, CE, 60455-970, Brazil

    M. C. de Mattos, T. S. Fonseca, T. Regis & D. Zampieri

  4. Instituto de Engenharias e Desenvolvimento Sustentável, Universidade da Integração Internacional da Lusofonia Afro-Brasileira, Acarape, CE, 62785-000, Brazil

    J. C. S. dos Santos

  5. Department of Inorganic Chemistry, Institute of Chemistry, State University of Campinas–UNICAMP, CP 6154, Campinas, SP, 13083-970, Brazil

    L. S. Costa

  6. Laboratório Nacional de Nanotecnologia (LNNano), Centro Nacional de Pesquisa em Energia e Materiais (CNPEM), CEP 13083-970, Campinas, SP, Brazil

    L. S. Costa

  7. Departamento de Física, Universidade Federal do Rio Grande do Norte, Natal, RN, 59078-900, Brazil

    M. A. Correa & F. Bohn

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  1. W. S. Galvão
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Galvão, W.S., Pinheiro, B.B., Golçalves, L.R.B. et al. Novel nanohybrid biocatalyst: application in the kinetic resolution of secondary alcohols. J Mater Sci 53, 14121–14137 (2018). https://doi.org/10.1007/s10853-018-2641-5

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