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Calix[n]arene Carboxylic Acid Derivatives as Regulators of Enzymatic Reactions: Enhanced Enantioselectivity in Lipase-Catalyzed Hydrolysis of (R/S)-Naproxen Methyl Ester

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Abstract

Candida rugosa lipase was immobilized with a sol–gel encapsulation procedure in the presence and absence of a calix[n]arene carboxylic acid derivative grafted onto magnetic nanoparticles or in the presence of the calix[n]arene carboxylic acid derivative with Fe3O4 magnetic nanoparticles as an additive. Through the enantioselective hydrolysis of racemic naproxen methyl ester and the hydrolysis of p-nitrophenylpalmitate, the relative enzyme activity was evaluated and tested. These results show that the encapsulated lipase without supports has lower conversion and enantioselectivity compared to the Calix[n]COOH-based encapsulated lipase. It has also been observed that the Calix[4]COOH-based encapsulated lipase has excellent enantioselectivity (enantiomeric ratio (E) > 400) as compared to encapsulated-free lipase enantioselectivity (E = 137), and it also has an enantiomeric excess value of ~98 % for S-naproxen.

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Acknowledgments

We would like to thank the Scientific and Technological Research Council of Turkey (TUBITAK grant number 111T027 and CMST COST Action CM1005) and the Research Foundation of Selcuk University (BAP) for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Selcuk University, 42031, Konya, Turkey

    Enise Akoz, Osman Y. Akbulut & Mustafa Yilmaz

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  1. Enise Akoz
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  2. Osman Y. Akbulut
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  3. Mustafa Yilmaz
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Correspondence to Mustafa Yilmaz.

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Akoz, E., Akbulut, O.Y. & Yilmaz, M. Calix[n]arene Carboxylic Acid Derivatives as Regulators of Enzymatic Reactions: Enhanced Enantioselectivity in Lipase-Catalyzed Hydrolysis of (R/S)-Naproxen Methyl Ester. Appl Biochem Biotechnol 172, 509–523 (2014). https://doi.org/10.1007/s12010-013-0527-1

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