Functional Group Effects of New Calixarene Derivatives on Catalytic and Enantioselective Behavior of Lipase

ABSTRACT

In this study, two new calixarene derivatives bearing thiourea and carbamate moieties were synthesized and characterized. Moreover, thiourea- and carbamate-bridged calixarene derivatives with Fe₃O₄ magnetic nanoparticle were employed for the first time as the convenient additives in the encapsulation process of lipase. The results of catalytic activity and enantioselectivity of the encapsulated lipases in the hydrolysis reaction of racemic flurbiprofen methyl ester indicate that both of the encapsulated lipases (Enc-TuC[4]@Fe₃O₄ and Enc-CbC[4]@Fe₃O₄) exhibit higher conversion and enantioselectivity compared to the free-encapsulated lipase (Enc-Lipase). However, the highest affinities result was obtained when the encapsulated lipase (Enc-CbC[4]@Fe₃O₄) was used in the kinetic resolution reaction of racemic flurbiprofen methyl ester.

KEYWORDS:

• Calixarene
• enantioselectivity
• Fe₃O₄nanoparticles
• flurbiprofen
• lipase

Funding

This work was supported by the Research Foundation of Selcuk University (BAP grant no. 15201004), Konya, Turkey.