Lipase esterification

The one-pot dynamic kinetic resolution (DKR) of ( )-l-phenylethanol lipase esterification in the presence of zeolite beta followed by saponification leads to (R)-l phenylethanol in 70 % isolated yield at a multi-gram scale. The DKR consists of two parallel reactions kinetic resolution by transesterification with an immobilized biocatalyst (lipase B from Candida antarctica) and in situ racemization over a zeolite beta (Si/Al = 150). With vinyl octanoate as the acyl donor, the desired ester of (R)-l-phenylethanol was obtained with a yield of 80 % and an ee of 98 %. The chiral secondary alcohol can be regenerated from the ester without loss of optical purity. The advantages of this method are that it uses a single liquid phase and both catalysts are solids which can be easily removed by filtration. This makes the method suitable for scale-up. The examples given here describe the multi-gram synthesis of (R)-l-phenylethyl octanoate and the hydrolysis of the ester to obtain pure (R)-l-phenylethanol. 

Index Entries Monolaurin immobilized lipase esterification experimental design solvent-free medium. 

Colombie, S., Tweedell, R. J., Condoret, J. S., and Marty, A., Water activity control a way to improve the efficiency of continuous lipase esterification, Biotechnol. Bioeng., 60, 362-368, 1998. 

PBHF 500 nm Lipase esterification of dodecanol and decanoic acid [109]... 

Young, Y. P, and B. Al-Duri. 1996. Kinetic Studies on Immobilised Lipase Esterification of Oleic Acid and Octanol. Journal of Chemical Technology Biotechnology 65 239-248. 

Stamatis, H., Kolisis, F.N., Xenakis, A., Bornscheuer, U., Scheper, T., Menge, U. 1993. Pseudomonas cepacia lipase Esterification reactions in AOT microemulsion systems. Biotechnol. Lett. 15, 703-708. 

Figure 5. Possible processes for the synthesis of DHA and DPA concentrates from fish oils (modified after Haraldsson and Hjaltason, 2001). (1), Pseudomonas fluorescens lipase hydrolysis of tuna oil, resulting in 80% DHA+EPA in free fatty acids (Rakshit et al, 2000). (2), Rhizomucor miehei lipase ethanolysis of free fatty acids of tuna oil, resulting in 74% DHA + 3% EPA in free fatty acids (Haraldsson and Kristinsson, 1998). (3), Pseudomonas sp. lipase ethanolysis of fish oil, resulting in 50% EPA+DHA in acylglycerols (Haraldsson et al., 1997). (4), Two-step process Pseudomonas sp. lipase ethanolysis, resulting in 46% EPA+DHA in acylglycerols followed by urea fractionation, resulting in 85% EPA+DHA (Breivik era/., 1997). (5), Novozymes 435 lipase esterification of PUFA from cod liver oil with glycerol, resulting in >70% EPA+DHA in triacylglycerols (Esteban Cerdan et al., 1998).

Keywords Biocatalysis, silicone, enzyme, lipase, esterification, copolymer, polyester, polyamide, polycaprolactone,... 

Cemia and Palocci [27] Review, lipase Esterification CO2 and others ... 

Snyder, King, Jackson [68] Van Eijs et al. [69] Lipase esterification of hexanoic acid with hexanol Methylation of lipids Transesterification Supercritical fluids CO2 Continuous and extractive... 

Vija, Telling, Tougu [70] Lipase Esterification CO2, n-hexane reaction... 

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