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Aldol Reactions by Lipase From Rhizopus niveus, an Example of Unspecific Protein Catalysis

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Abstract

The lipase from Rhizopus niveus (RNL) catalyzed by unspecific protein catalysis the aldol reactions between cyclohexanone and aromatic aldehydes in organic solvents with water or aqueous buffer solution. The reactional conditions strongly influenced the yield (0–99%) and enantioselectivities in the anti-products (6–55% ee anti ). The aldol products with enantioselectivities in the anti-product were observed for inactive enzyme and in denaturing conditions. Therefore, the reactions in the evaluated conditions proceeded by unspecific protein catalysis with moderate enantioselectivities and not by promiscuous activity. These enzymatic studies identify a new green catalyst for aldol reactions and new possibilities for lipases, especially for the use of the lipase RNL, which has been scarcely reported in the literature and catalyzed the aldol reaction between different aromatic aldehydes and cyclohexanone.

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Acknowledgements

The authors would like to acknowledge Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq/PVE, Grant No. 400202/2014-0) and Fundação de Amparo à pesquisa do Estado de São Paulo (FAPESP, Grant No. 2014/18257-0) for their financial support. W. G. Birolli is grateful to CNPq for his scholarship (Grant No. 141656/2014-0) and to the Institute for Bioengineering and Biosciences, University of Lisbon, for availability and collaboration.

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Authors and Affiliations

  1. Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa Angelina, São Carlos, SP, 13563-120, Brazil

    Willian G. Birolli & André L. M. Porto

  2. Bioengineering Department, Institute for Bioengineering and Biosciences, Instituto Superior Técnico, University of Lisbon, Av. Rovisco Pais, Lisbon, 1049-001, Portugal

    Luis P. Fonseca

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  1. Willian G. Birolli
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  2. Luis P. Fonseca
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  3. André L. M. Porto
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Correspondence to André L. M. Porto.

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Birolli, W.G., Fonseca, L.P. & Porto, A.L.M. Aldol Reactions by Lipase From Rhizopus niveus, an Example of Unspecific Protein Catalysis. Catal Lett 147, 1977–1987 (2017). https://doi.org/10.1007/s10562-017-2121-6

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  • DOI: https://doi.org/10.1007/s10562-017-2121-6

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