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Open AccessFeature PaperArticle

Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity

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Graduate Program in Chemical Engineering, Federal University of Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil
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Department of Chemical Engineering, Federal University of Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil
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Institute of Chemistry, Federal University of Alfenas, 37130-001 Alfenas, MG, Brazil
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Departamento de Biocatálisis, ICP–CSIC, Campus UAM, Cantoblanco, 28049 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Catalysts 2020, 10(2), 218; https://doi.org/10.3390/catal10020218
Received: 22 January 2020 / Revised: 7 February 2020 / Accepted: 8 February 2020 / Published: 11 February 2020
The present study aims the enzymatic synthesis of solketal palmitate by esterification between solketal and palmitic acid using heptane as solvent. Lipases from Thermomyces lanuginosus (TLL), Candida rugosa type VII (CRL), and Pseudomonas fluorescens (PFL) were immobilized via interfacial activation on rice husk silica functionalized with triethoxy(octyl)silane (Octyl–SiO2) and used as biocatalysts. A loading of 20–22 mg of lipase/g of support was immobilized independently of the studied enzyme. TLL–Octyl–SiO2 was the most active biocatalyst in oil hydrolysis (656.0 ± 23.9 U/g) and ester synthesis (productivity of 6.8 mmol/min.gbiocat), and it has been chosen for further ester synthesis optimization. The effect of some important parameters such as biocatalyst concentration, reaction temperature and acid:alcohol molar ratio on the reaction has been evaluated using a central composite rotatable design at fixed mechanical stirring (240 rpm) and reaction time (15 min). Subsequently, the effect of reactants concentration and molecular sieve concentration has also been examined. Under optimal conditions (56 °C, acid:alcohol molar ratio of 1:3 with a palmitic acid concentration of 1 M, and 20% wt. of TLL–Octyl–SiO2 per volume of reaction mixture), 83% acid conversion was obtained after 150 min of reaction. The biocatalyst retained 87% of its initial activity after seven successive reaction batches. The product was identified by nuclear magnetic resonance analysis. Antimicrobial activity studies showed that the synthesized ester demonstrated antifungal activity against Candida albicans and Candida parapsilosis, with minimum inhibitory concentration (MIC) between 200 and 400 µg/mL, and bacteriostatic/fungistatic action – minimum microbicial concentration (MMC)>400 µg/mL.
Keywords: solketal ester; immobilized lipase; esterification; optimization; structural characterization; antimicrobial activity solketal ester; immobilized lipase; esterification; optimization; structural characterization; antimicrobial activity
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Mendoza-Ortiz, P.A.; Gama, R.S.; Gómez, O.C.; Luiz, J.H.H.; Fernandez-Lafuente, R.; Cren, E.C.; Mendes, A.A. Sustainable Enzymatic Synthesis of a Solketal Ester—Process Optimization and Evaluation of Its Antimicrobial Activity. Catalysts 2020, 10, 218.

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