Lipase Catalyzed Synthesis of Aromatic Esters of Sugar Alcohols

Authors: R. Croitoru, L. A. M. van den Broek, A. E. Frissen, C. M. Davidescu, F. Peter, C. G. Boeriu

Abstract:

Commercially available lipases (Candida antarctica lipase B, Novozyme 435, Thermomyces lanuginosus lipase, and Lipozyme TL IM), as well as sol-gel immobilized lipases, have been screened for their ability to acylate regioselectively xylitol, sorbitol, and mannitol with a phenolic ester in a binary mixture of t-butanol and dimethylsulfoxide. HPLC and MALDI-TOF MS analysis revealed the exclusive formation of monoesters for all studied sugar alcohols. The lipases immobilized by the sol-gel entrapment method proved to be efficient catalysts, leading to high conversions (up to 60%) in the investigated acylation reactions. From a sequence of silane precursors with different nonhydrolyzable groups in their structure, the presence of octyl and i-butyl group was most beneficial for the catalytic activity of sol-gel entrapped lipases in the studied process.

Keywords: Lipase, phenolic ester, specificity, sugar alcohol, transesterification.

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1082706

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