Substrate selectivity in esterification of less common fatty acids catalysed by lipases from different sources

Jachmanián, Iván; Schulte, E.; Mukherjee, Kumar D.

doi:10.1007/bf00172486

Cited by 40 publications

(31 citation statements)

References 19 publications

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“…γ-Linolenic acid GLA has been purified to 90 in the free fatty acid fraction after selective esterification of fatty acid from borage oil with n-butanol 12 . Also, ethyl EPA was enriched by selective alcoholysis of ethyl esters with lauryl alcohol using Lipozyme RM IM 13 .…”

Section: Effect Of Alcoholmentioning

confidence: 99%

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Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography

Baik

Kim

et al. 2015

J. Oleo Sci.

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Section: Effect Of Alcoholmentioning

confidence: 99%

“…There have been several studies of lipase-catalyzed esterifications using fatty acids and alcohols 12,13,18 . The appropriate molar ratio of fatty acid in the 1 st reaction mixture to ethanol was examined in a PBR, and the results are shown in Fig.…”

Section: Effect Of Molar Ratiomentioning

confidence: 99%

Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography

Baik

Kim

et al. 2015

J. Oleo Sci.

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“…Bottino et al [26] theorized that the resistance of certain long chain PUFA to enzymatic hydrolysis could be attributed to the inhibitory effect of a double bond located close to the carboxylic group or to the presence of multiple cis double bonds which force the terminal methyl group of the fatty acid to lie close to the ester bond and sterically hinder lipase action. In addition, Jachmanian et al [27] observed that C. rugosa lipase strongly discriminates against unsaturated fatty acids having the first double from the carboxyl end at an even numbered carbon. The presence of a double bond on C-6 of SDA and GLA distinguishes these fatty acids from other 18 carbon unsaturated fatty acids in SDASO and may therefore serve as a structural basis for their resistance to C. rugosa lipasecatalyzed hydrolysis.…”

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Method for Producing Stearidonic Acid Concentrates from Stearidonic Acid Soybean Oil

Ifeduba

Akoh

2013

J Americ Oil Chem Soc

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The aim of this study was to produce stearidonic acid (SDA, 18:4n‐3) omega‐3 concentrates from 25 % SDA soybean oil (SDASO) by enzymatic acidolysis. Substrates were prepared by chemical and enzymatic hydrolysis of SDASO. A 62 % SDA free fatty acid mixture (SDA‐FFA) was obtained by low temperature crystallization of the chemical hydrolyzate while partial hydrolysis of SDASO by non‐immobilized lipase AY 30 (Candida rugosa) yielded a 51 % SDA acylglycerol mixture (SDA‐GLY). Reaction conditions for acidolysis between SDA‐FFA and SDA‐GLY were optimized using response surface methodology (RSM). Incorporation of SDA into SDA‐GLY by immobilized Lipozyme RM IM (Rhizomucor miehei) and non‐immobilized Lipomod 34P‐LO34P (C. cylindracea [rugosa]) lipases were modeled under varying levels of the substrate molar ratio (Sr), temperature (T), and time (t). Optimal conditions for production of a 60 % SDA concentrate were predicted to be Sr = 4.8, T = 65 °C and t = 8 h for Lipozyme RM IM and Sr = 5.0, T = 43 °C and t = 48 h for Lipomod 34P‐L034P. The model was verified experimentally by gram scale synthesis under optimal conditions which resulted in the production of 59.98 and 58.98 % SDA concentrates (≥96 % triacylglycerols) by Lipozyme RM IM and Lipomod 34P‐L034P, respectively.

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“…After the esterification, the DHA concentration increased 3.5-fold, whereas the concentration of the other fatty acids decreased. In previous reports involving the investigation of the fatty acid specificity of the lipase from Rhizomucor miehei, there was a significant level of discrimination observed during the esterification of fatty acids with 1-butanol between unsaturated fatty acids having a (or first) cis-4, a cis-6, or a cis-8 unsaturated bond compared with other fatty acids [41,42]. In particular, the rate of DHA esterification in fatty acids containing double bonds starting from cis-4 was significantly lower than that of the others.…”

Section: Water Content Vs Residence Timementioning

confidence: 99%

Enrichment of DHA from Tuna Oil in a Packed Bed Reactor via Lipase‐Catalyzed Esterification

Hong¹,

Ma²,

No³

et al. 2014

J Americ Oil Chem Soc

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A packed‐bed reactor (length 6.5 cm; id 4.65 mm) has been used to enrich docosahexaenoic acid (DHA) via the lipase‐catalyzed esterification of the fatty acid from tuna oil with ethanol. Lipozyme RM IM (from Rhizomucor miehei) was used for the esterification reaction because of its ability to discriminate between different fatty acids, and several reaction parameters, including the temperature, molar ratio of substrates, and water content were explored as a function of residence time. In this way, the optimum conditions for the enrichment process were determined to be a temperature of 20 °C, a molar ratio of 1:5 (i.e., fatty acid to ethanol), and a water content of 1.0 % (based on the total substrate weight). Under these conditions, a residence time of 90 min gave a DHA concentration of 70 wt% and a DHA recovery yield of 87 wt% in the residual fatty acid fraction.

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Substrate selectivity in esterification of less common fatty acids catalysed by lipases from different sources

Cited by 40 publications

References 19 publications

Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography

Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography

Chemoenzymatic Method for Producing Stearidonic Acid Concentrates from Stearidonic Acid Soybean Oil

Enrichment of DHA from Tuna Oil in a Packed Bed Reactor via Lipase‐Catalyzed Esterification

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