Synthesis of CLA‐enriched TAG by <i>Candida antarctica</i> lipase under vacuum

Hong, Seung In; Kim, Yangha; Yoon, Sung Won; Cho, Seung Yong; Kim, In Hwan

doi:10.1002/ejlt.201100233

Cited by 21 publications

(9 citation statements)

References 45 publications

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“…d). The trend was similar to the effect of enzyme loading on esterification between conjugated linoleic acid and glycerol catalyzed by Novozym 435 under vacuum (Hong et al, ). It was observed that the reactants could not be well agitated when enzyme dosage exceeded 100% based on AKG if transesterification was carried out in a solvent‐free system.…”

Section: Resultssupporting

confidence: 79%

Enzymatic Synthesis of Ether Lipids Rich in Docosahexaenoic Acid with Squalene as Reaction Medium

Sun

Zhang

Wang

et al. 2019

J Americ Oil Chem Soc

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Using squalene as reaction medium was tried for the enzymatic synthesis of ether lipids rich in docosahexaenoic acid (DHA) via transesterification of alkylglycerols (AKG) obtained from shark liver oil and DHA-enriched ethyl esters (DHA-EE) from Schizochytrium sp. The effects of reaction time, temperature, molar ratio (AKG /DHA-EE), and enzyme dosage were investigated. DHA conversion of 74.47% was achieved for 48 hours of reaction at 60 C using a molar ratio of 1:2 and an enzyme dosage of 30% based on AKG in the presence of squalene with Lipozyme ® 435 (Novozymes, Tianjin, China) as the catalyst. With a high boiling point, squalene could act as a solvent without being vaporized from the reaction system under vacuum and improve the operational stability of immobilized lipase, which may be useful for enzymatic reactions under vacuum for lipid modification with byproducts of low boiling points.The scaled-up reactions were performed at 60 C for 48 hours with a Lipozyme 435 dosage of 30%, and the 138 J Am Oil Chem Soc J Am Oil Chem Soc (2020) 97: 135-140

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Section: Resultssupporting

confidence: 79%

Enzymatic Synthesis of Ether Lipids Rich in Docosahexaenoic Acid with Squalene as Reaction Medium

Sun

Zhang

Wang

et al. 2019

J Americ Oil Chem Soc

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“…LPC exists naturally on cell membranes as a minor component and has been widely used in the food, cosmetic, and pharmaceutical industries as emulsifier or medicine . LPC has been shown to be a preferred carrier form of FAs compared with triacylglycerols (TAG) and free FA, because it is more bioavailable than FAs in the TAG form and more stable and suitable for ingestion than FAs in the free FA form …”

Section: Introductionmentioning

confidence: 99%

Synthesis of CLA‐Rich Lysophosphatidylcholine by Immobilized MAS1‐H108A‐Catalyzed Esterification: Effects of the Parameters and Monitoring of the Reaction Process

Wang

Zhang

et al. 2018

Euro J Lipid Sci & Tech

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Conjugated linoleic acid (CLA)‐rich lysophosphatidylcholine (LPC) with many proven beneficial effects is successfully synthesized by an immobilized mutant lipase (MAS1‐H108A)‐catalyzed esterification of glycerophosphorylcholine (GPC) and CLA‐rich FAs. Under the optimized conditions (temperature of 55 °C, substrate molar ratio of CLA‐rich FAs to GPC of 40:1, and enzyme loading of 300 U g−1), LPC content as high as 89.10 mol.% is achieved, which is exceptionally higher than any ever‐reported value. By monitoring the esterification process, it is found that sn1‐LPC is easy to synthesize and is the predominant product, while sn2‐LPC and phosphatidylcholine (PC) are difficult to synthesize and are with lower content in the final product. The formed sn2‐LPC during esterification may mainly attribute to the acyl migration of sn1‐LPC and the ratio of sn1‐LPC to sn2‐LPC finally plateaus at approximately 7. Besides, our results also demonstrate that sn2‐LPC is the main template for the synthesis of PC. Finally, a complete reaction scheme for the synthesis of LPC by immobilized MAS1‐H108A‐catalyzed esterification of GPC and fatty acids is mapped out. Overall, the highest LPC content can be obtained by immobilized MAS1‐H108A‐catalyzed esterification and there is the first study for systematical studying the reaction process of CLA‐rich LPC synthesis. Practical Applications: Previous studies have demonstrated that Novozym 435 is the most suitable catalyst for the synthesis of CLA‐rich LPC. However, the LPC content obtained by Novozym 435 is only 70 mol.% and the reaction process for the synthesis of CLA‐rich LPC has not been studied systematically, which restricts the commercial production of CLA‐rich LPC in some extent. Therefore, further exploration of alternative enzyme resources for highly efficient synthesis of CLA‐rich LPC and trying to clarify the reaction process of CLA‐rich LPC synthesis are of significant importance for the future commercially industrial production of CLA‐rich LPC. A complete reaction scheme for the synthesis of LPC using GPC and FAs as substrates by immobilized MAS1‐H108A‐catalyzed esterification. CLA‐rich FAs are used as model FAs in this study. Reaction parameters, such as temperature, CLA‐rich FAs/GPC ratio, and enzyme loading are selected to study their effects on the esterification. Concurrently, the reaction process is monitored. LPC content as high as 89.10 mol.% is obtained, which is the highest reported value thus far for the synthesis of CLA‐rich LPC. Finally, the reaction scheme for the synthesis of LPC by immobilized MAS1‐H108A‐catalyzed esterification is mapped out.

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“…However, we observed a different result in the present work that not only the TAG content but also the EE conversion was affected by the enzyme dosage: higher enzyme dosage led to higher EE conversion and TAG content. Hong et al (2012) also found an increase in the conversion of TAG when enzyme loading was increased from 5% to 10% throughout the course of esterification between conjugated linoleic acid and glycerol.…”

Section: Effect Of Substrate Ratios On Glycerolysismentioning

confidence: 70%

Preparation of Triacylglycerols Enriched in DHA from Single Cell Glycerides via Molecular Distillation and Enzymatic Glycerolysis

Sun

Yang

Xue

et al. 2014

Journal of Aquatic Food Product Technology

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In the present study, the total lipids from Schizochytrium sp. were ethylated, and ethyl esters (EE) enriched in C22:6n-3(DHA) were obtained through molecular distillation and converted to glyceride form via lipase-catalyzed glycerolysis under vacuum with activated clay as absorbents in non-solvent system. Total lipids were extracted from dry powder of Schizochytrium sp., which was followed by lipase catalyzed ethylation. EE with 83.04% DHA Downloaded by [North Carolina State University] at 08:41 30 March 2015 ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2 was obtained through a three-stage procedure of molecular distillation. The effect of vacuum, temperature, reaction time, substrate ratio, and enzyme dosage on glycerolysis was investigated.Vacuum and increase in temperature had a positive effect on glycerolysis, and the increase in substrate ratio led to an increase in TAG content but a decrease in EE conversion. The adsorption of glycerol onto activated clay played a positive role in glycerolysis, and the operational stability of immobilized lipase. The conditions which gave the glycerides with more than 75% TAG were 60°C, 24h, 0.048mol EE, 0.016mol glycerol, 2.25g activated clay, and 3% Lipozyme435, and the immobilized lipase showed good operational stability in 10 batches of reactions with activated clay as absorbent.

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Synthesis of CLA‐enriched TAG by Candida antarctica lipase under vacuum

Cited by 21 publications

References 45 publications

Enzymatic Synthesis of Ether Lipids Rich in Docosahexaenoic Acid with Squalene as Reaction Medium

Enzymatic Synthesis of Ether Lipids Rich in Docosahexaenoic Acid with Squalene as Reaction Medium

Synthesis of CLA‐Rich Lysophosphatidylcholine by Immobilized MAS1‐H108A‐Catalyzed Esterification: Effects of the Parameters and Monitoring of the Reaction Process

Preparation of Triacylglycerols Enriched in DHA from Single Cell Glycerides via Molecular Distillation and Enzymatic Glycerolysis

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