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Efficient Candida rugosa lipase immobilization on Maghnite clay and application for the production of (1R)-(−)-Menthyl acetate

Fatiha Benamia, Sabrina Benouis, Abderahmane Belafriekh, Noura Semache, Nacer Rebbani, and Zeineddine Djeghaba

Laboratory of Applied Organic Chemistry, Chemistry Department, Faculty of Sciences, Badji Mokhtar University, Annaba, Algeria



Abstract: This work focused on the identification of natural, economical, and efficient supports for immobilization of Candida rugosa lipase (CRL) to catalyze the resolution of (±)-menthol. To this purpose, CRL has been immobilized on natural montmorillonite from Algeria (Maghnite-H), ion-exchange resins (Amberjet®1200-H and Amberjet®4200-Cl), and diatomaceous earth (Celite®545). After a preliminary screening of supports, the immobilization of CRL led to a markedly improved enantioselectivity. Excellent enantioselectivity (E ≥ 134) was achieved by the four supported lipases (E = 68 for free enzyme). Compared to the three other supports tested, higher enantioselectivity was observed with Maghnite-H used as immobilization matrix. In this work, the effects of solvent, reaction time, and temperature, on the conversion as well as on enantioselectivity were investigated. The maximum of conversion (% C = 43%) with high enantiomeric excess of products (eep > 99) was obtained when the reaction is catalyzed by CRL immobilized on Maghnite-H at 30 °C for 24 h, and using toluene as selected solvent. Immobilized CRL on Maghnite-H exhibited good thermostability over a wide temperature range (30–90 °C) compared to the free one. These results suggest that CRL immobilized on Maghnite-H has good potential as biocatalyst for the production of (1R)-(−)-menthyl acetate.

Keywords: Maghnite clay; Candida rugosa lipase; Immobilization effect; Biocatalysis; (1R)-(−)-Menthyl acetate; Transesterification;

Full paper is available at

DOI: 10.1007/s11696-016-0080-9


Chemical Papers 71 (4) 785–793 (2017)

Monday, June 17, 2024

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