Esterification of fatty acids using Candida antarctica lipase A in water-abundant systems

Abstract

The feasibility of using native lipase A from Candida antarctica (CAL-A) to esterify fatty acids with water-insoluble alcohols in the presence of excess water was investigated in stirred-tank reactors. For high reaction rates, a ratio of water:substrates of 0.6-1.4:1 (v/v) was required. CAL-A showed higher substrate selectivity for the esterification of saturated palmitic acid with branched-chain 2-ethyl-1-hexanol than for unsaturated oleic acid with linear alcohol (1-decanol). After 18 h at 70 °C in a 1.5 l bulk stirred-tank reactor, an 2-ethyl-1-hexyl palmitic acid ester was obtained near 100 % yield [molar ratio palmitic acid:2-ethyl-1-hexanol ~1:1.25, with 1.11 % (w/w) Novocor ADL (based on palmitic acid weight)].

The 3D model of the lipase/acyltransferase from Candida parapsilosis, a tool for the elucidation of structural determinants in CAL-A lipase superfamily

“…One is the esterification of free fatty acids, where a lipase is used to catalyze reverse hydrolysis to reach the thermodynamic equilibrium of the hydrolysis/ esterification reaction. This has been successfully used in various studies, for example with lipases from Candida deformans, Mucor miehei, Rhizopus delemar, Pseudomonas fluorescens, Rhizopus arrhizus or with lipase A from P. antarctica [9][10][11][12][13][14][15]. With such lipases, a so-called transesterification can also be obtained through the hydrolysis of an ester substrate followed by the re-esterification of the released fatty acids with an alcohol acceptor.…”

Fungal Screening on Olive Oil for Extracellular Triacylglycerol Lipases: Selection of a Trichoderma harzianum Strain and Genome Wide Search for the Genes

“…Interestingly, 526309 does not belong to class 3 of the lipases and is not even annotated as TAG lipase in the genome database of T. harzianum but Brennes and Baeck [ 92 ] showed that CALA, its homologue, works on long-chain TAGs. Therefore, transfer function based on structure-homology predicts triacylglycerol lipolytic activity for 526309.…”

Biocatalytic solutions to cyclomethicones problem in cosmetics

“…Most processes are carried out with immobilized lipases in water‐free medium to shift equilibrium towards ester production. An exception is esters synthesis with free Candida antarctica lipase A in aqueous medium, reaching 100% conversion in 18 hours . Processes conducted in petroleum ether require also long times (10–24 h) and moderate conversions were obtained (90–91%) .…”