ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

E-mail: fatiha.benamia@univ-annaba.org

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 www.springerlink.com.

DOI: 10.1007/s11696-016-0080-9

Chemical Papers 71 (4) 785–793 (2017)