Lipase Catalyzed Synthesis of ABA-Type Structured Lipid from Single Cell Oil and Tripalmitin

Liu, Silei; Dong, Xuyan; Wei, Fang; Wang, Xiang; Lv, Xiongwen; Lin, Wang; Quek, Siew Young; Hong, Chen

doi:10.1111/jfpp.12843

Cited by 13 publications

(12 citation statements)

References 45 publications

(69 reference statements)

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“…However, acyl migration (AM), occurring and observed in regio-specific STs, even the region-specific lipase, used as a catalyst, which is well known as a severe problem in synthesis because of its lower purity and generation of free fatty acids, monoglycerols (MGs), diglycerols (DGs), and TGs, seriously influences the quality and total yield of STs. Moreover, AM cannot be easily avoided as a side reaction during the process of LCSs [5,6].…”

Section: Introductionmentioning

confidence: 99%

A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications

Mao

et al. 2019

IJMS

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Acyl migration (AM) is the main side reaction in the large-scale, regio-specific lipase catalyzed production of structural triglycerides (STs). A detailed understanding of the mechanism of AM was obtained during the process of lipase-catalyzed schemes (LCSs), which play a vital role in improving the quality and total yield of STs. However, currently, the mechanism of AM remains controversial. Herein, the two mechanisms (non-catalyzed (NCM) and lipase-catalyzed (LCM)) of AM have been analyzed in detail by the density functional theory (DFT) at the molecular level. Based on the computational results, we concluded that the energy barrier of the rate-limiting step in the LCM was 18.8 kcal/mol, which is more in agreement with the available experimental value (17.8 kcal/mol), indicating that LCM could significantly accelerate the rate of AM, because it has an energy barrier ~2 times lower than that of the NCM. Interestingly, we also found that the catalytic triad (Asp-His-Ser) of the lipase and water could effectively drop the reaction barrier, which served as the general acid or base, or shuttle of the proton.

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Section: Introductionmentioning

confidence: 99%

A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications

Mao

et al. 2019

IJMS

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“…Generally, Lipozyme RM IM is used in acidolysis ( 15 , 16 , 39 - 53 ), although several studies also use it in transesterification reactions ( 43 , 54 , 55 ). Lipozyme TL IM is usually used in transesterification reaction ( 56 - 59 ), but some reported works also use it in acidolysis ( 6 , 16 , 60 - 62 ).…”

Section: Lipase For Hmfs Synthesismentioning

confidence: 99%

“…Generally, Lipozyme RM IM is used in acidolysis reaction (15,16,38,39,(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52). In addition, several studies also use Lipozyme RM IM in transesterification reactions (42,53,54). Meanwhile, Lipozyme TL IM is usually used in transesterification reaction (55)(56)(57)(58).…”

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confidence: 99%

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Enzymatic Synthesis of Human Milk Fat Substitute - A Review on Technological Approaches

Hasibuan

Sitanggang

Andarwulan

et al. 2021

Food Technol. Biotechnol. (Online)

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Human milk fat substitute (HMFS) is a structured lipid designed to resemble human milk fat. It contains 60-70 % palmitic acid at the sn-2 position and unsaturated fatty acids at the sn-1,3 positions in triacylglycerol structures. HMFS is synthesized by the enzymatic interesterification of vegetable oils, animal fats, or blend of oils. The efficiency of HMFS synthesis can be enhanced through the selection of appropriate substrates, enzymes, and reaction methods. This review focuses on the synthesis of HMFS by lipase-catalyzed interesterification. This work provides a detailed overview of biocatalysts, substrates, synthesis methods, factors influencing the synthesis, and purification process of HMFS. Major challenges and future research in the synthesis of HMFS are also discussed. This review can be used as an information for developing future strategies in producing HMFS.

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“…Structured lipids can be produced by different methods, and the chemical and enzymatic interesterifications are the most used (Javidipour and Tunçtürk, 2007; Liu et al., 2017; Sivakanthan et al., 2019). The enzymatic process is advantageous and has greater selectivity (Lakum and Sonwai, 2018; Xie & Zang, 2016); however, the use of enzymes is expensive, difficult to separate and reuse (Wang et al., 2012; Zhao et al., 2007).…”

Section: Introductionmentioning

confidence: 99%

Structured lipids of swine lard and oils from byproducts of skipjack tuna and of common carp

Engelmann

Peres

Igansi

et al. 2020

J. Food Process. Preserv.

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The aim was to obtain structured lipids by chemical interesterification of saturated fat (lard) with bleached oils from fish heads (carp and tuna). All materials were characterized by physicochemical analyses, gas chromatography for fatty acid profiles, nuclear magnetic resonance for unsaturated fatty acids esterified in sn‐1,3 and sn‐2 positions of the triacylglycerols, and differential scanning calorimetry for solid fat content (SFC). The amounts of eicosapentaenoic acid and docosahexaenoic acid were much higher for tuna oil (32%), showing the presence of docosahexaenoic acid in the structured lipids. The higher modifications of lard were with 1% of catalyst and 70:30 ratio of lard : fish oil. Through the SFC analysis, information about the structured lipids’ characteristics were obtained, making it possible to define the most suitable technological applications. After the reaction, SFC reduced from 2% to 30% when compared to the swine lard, and the highest changes had occurred when tuna oil was used. Practical applications In recent years, the growing demand for foods with nutritional properties has aroused the interest about the development of a new generation of lipids, the so‐called healthy lipids. This work presents as a differential, the effect evaluation of the fish oils from different cultures (pisciculture and mariculture) in the characteristics of structured lipids, which are obtained by chemical interesterification reaction of these oils with swine lard. The presence of different types of fatty acids in the same triacylglycerol molecule can produce a compound with unique nutritional and metabolic properties. Thus, the use of fish oils with different fatty acid profiles can have a direct effect on the technological applications of the structured lipids. In addition, the incorporation of fatty acids as EPA and DHA, which are not naturally found in fats, besides conferring interesting technological characteristics, increases the nutritional value of the fat.

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Lipase Catalyzed Synthesis of ABA-Type Structured Lipid from Single Cell Oil and Tripalmitin

Cited by 13 publications

References 45 publications

A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications

A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications

Enzymatic Synthesis of Human Milk Fat Substitute - A Review on Technological Approaches

Structured lipids of swine lard and oils from byproducts of skipjack tuna and of common carp

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