Synthesis of a glutaraldehyde derivative of calix[4]arene as a cross-linker reagent for lipase immobilization

This article describes the synthesis of a new calix[4]arene 1,3-distal glutaraldehyde derivative 4 as a cross-linker-reagent for immobilization of Candida rugosa lipase (CRL). p-tert-Butylcalix[4]arene 1,3-distal diaminoalkyl derivative (3) synthesized via aminolysis reaction of 5,11,17,23-tert-butyl-25,27-ethoxycarbonylmethoxy-26,28-hydroxycalix[4]arene (2) with 1,8-diaminooctane. Compound 3 was converted to its aldehyde derivative (4) by the treatment with glutaraldehyde solution. 4 was used in lipase immobilization in order to see the role of calix[4]arene binding site on the lipase activity and stability. It was observed that the immobilized lipase activity was maintained at levels exceeding 95% of its original activity after 40 min.