Preparation of One‐Pot Immobilized Lipase with Fe₃O₄ Nanoparticles Into Metal‐Organic Framework For Enantioselective Hydrolysis of (R,S)‐Naproxen Methyl Ester

Abstract

Immobilization of enzyme to magnetic metal‐organic frameworks (MOF) can preserve biological functionality in harsh environments to increase enzymes activity, stability, and improve reusability. The magnetic Fe3O4 nanoparticles were treated with calix[4]arene tetracarboxylic acid (Calix) and Candida rugosa lipase (CRL), and then encapsulated into the zeolitic imidazole framework‐8 (Fe3O4@Calix‐ZIF‐8@CRL). The lipase activity data of Fe3O4@Calix‐ZIF‐8@CRL was 2.88 times higher than that of the Fe3O4@ZIF‐8@CRL (without Calix). The catalytic properties of immobilized lipases were studied on the enantioselective hydrolysis of R/S‐naproxen methyl ester. It was also observed that Fe3O4@Calix‐ZIF‐8@CRL has excellent enantioselectivity (E=371) compared to Fe3O4@ZIF‐8@CRL (E=131). Furthermore, Fe3O4@Calix‐ZIF‐8@CRL was seen to still retain 30 % of the conversion rate after the fifth reuse. This work may also be useful for the pharmaceutical industry due to the increased reusability and stability of enzymes, the enantiomeric selectivity exhibited by MOF‐enzyme biocomposites, and the significant differences in the biological activities of the enantiomers.

Efficient resolution of 4‐chlormandelic acid enantiomers using lipase@UiO‐67(Zr) zirconium–organic frameworks in organic solvent

“…The progress has been achieved in the area of chiral resolution employ lipase immobilization on MOF materials. [22][23][24][25][26][27][28][29][30][31] It can be meet the basic requirements of enzyme immobilization.…”

“…In recent years, the development of MOF materials with high surface area and pore volume, pore size can be adjusted, and materials surface can be modified. The progress has been achieved in the area of chiral resolution employ lipase immobilization on MOF materials 22–31 . It can be meet the basic requirements of enzyme immobilization.…”

Application of novel Fe3O4/Zn-metal organic framework magnetic nanostructures as an antimicrobial agent and magnetic nanocatalyst in the synthesis of heterocyclic compounds

“…The importance of these compounds in the synthesis of organic compounds is their easy separation after performing the reaction by a magnet ( Yao et al, 2016 ; Ghorbani-Choghamarani and Taherinia, 2020 ). Biological properties such as enzyme immobilization, enantioselective hydrolysis of (R, S)-naproxen methyl ester, and immobilization of proline activated lipase from magnetic MOF compounds have been reports ( Nadar and Rathod, 2018 ; Nadar and Rathod, 2020 ; Ozyilmaz et al, 2021 ).…”

Lipase Immobilized onto Metal‐Organic Frameworks for Enantioselective Resolution of Mandelic Acid

“…Moreover, MOFs show superior chemical stability, excellent mechanical strength, ease modification on both metal nodes and ligands [14,15], facile alteration of pore diameters, and ample reactive functional groups such as amino, carboxyl, and hydroxyl on the surface of a support, so it was considered to be a promising carrier for enzyme immobilization [16]. However, the MOFs immobilized enzymes for enantioselective kinetic resolution of racemates is still underdeveloped [17][18][19]. Therefore, the development of immobilized enzymes with MOFs for efficient resolution of enantiomers is highly desirable.…”