Deep Eutectic Solvents Enable the Enhanced Production of <i>n‐3</i> PUFA‐Enriched Triacylglycerols

Xu, Long; Zhang, Li; Li, Daoming; Liu, Pengzhan; Tan, Chin Ping; Wang, Weifei; Liu, Xiangqian; Yang, Bo; Lan, Dongming; Wang, Yonghua

doi:10.1002/ejlt.201700300

Cited by 8 publications

(8 citation statements)

References 30 publications

(29 reference statements)

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“…The maximal n-3 PUFA-rich TAG content 55.8 with similar n-3 PUFA composition to the substrate was obtained at 12 h in CG system. There was a 1.38-fold increase of TAG content in CG system compared with that in the solvent-free system in this study, which was higher than that 1.2-fold at 48 h obtained by Novozym 435 in the literature 48 . It could be concluded that the catalytic efficiency of immobilized MAS1 lipase was better than that of Novozym 435.…”

Section: 3contrasting

confidence: 75%

Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents

et al. 2021

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ed significant attention by virtue of its high catalytic efficiency, mild reaction conditions, wide fatty acid selectivity, high positional and substrate selectivity when compared with chemical methods 12,13 . Enzymatic esterification and glycerolysis reactions have been widely employed to prepare n-3 PUFA-rich TAG. Nevertheless, the synthesized n-3 PUFA-rich TAG content is low and the separation and purification of the complex product are needed when enzymatic reactions are carried out in the solvent-free systems 8,14,15 . Although n-3 PUFA-rich TAG content is relatively high when enzymatic reactions are performed in the organic solvent systems, these organic solvents could cause food safety Abstract: n-3 polyunsaturated fatty acids (PUFA)-rich triacylglycerols (TAG) with many beneficial effects are still difficult to be synthesized efficiently and rapidly by current synthetic techniques. This study reports the fatty acid specificity of immobilized MAS1 lipase and its efficient synthesis of n-3 PUFA-rich TAG by esterification of glycerol with n-3 PUFA in natural deep eutectic solvents (NADES) systems. Immobilized MAS1 lipase showed the highest preference for capric acid [C10:0, the highest specificity constant (1/α)=1] whereas it discriminated strongly against docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) due to their lowest specificity constants (1/α=0.19 and 0.2). Moreover, the highest n-3 PUFA-rich TAG content (55.8%) with similar n-3 PUFA composition to the substrate was obtained in choline chloride/glycerol (CG) system. There was a 1.38-fold increase of TAG content in CG system compared with that in the solvent-free system. Interestingly, immobilized MAS1 lipase exhibited no regiospecificity in the solvent-free and various NADES systems. Besides, the potential reaction mechanism of immobilized MAS1 lipase-catalyzed esterification of glycerol with n-3 PUFA in NADES systems was described. It was found that the use of NADES as solvents could greatly enhance TAG content, and make it easy to separate the product. These results indicated that immobilized MAS1 lipase is a promising biocatalyst for the efficient synthesis of n-3 PUFA-rich TAG by esterification of glycerol with n-3 PUFA in NADES systems.

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Section: 3contrasting

confidence: 75%

Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents

et al. 2021

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“…10 On the basis of DESs, Dai et al ( 2013) 11 discovered that many plant abundant primary metabolites changed their state from solid to liquid when they were mixed in the proper ratio, resulting in the discovery of over 100 DESs from nature. 16 organic synthesis, 17 and electrochemistry. 18 Particularly, NADESs have been widely applied as the assisted extraction solvents for protein 16 and the thermal stability solvents of protein.…”

Section: Introductionmentioning

confidence: 99%

“…16 organic synthesis, 17 and electrochemistry. 18 Particularly, NADESs have been widely applied as the assisted extraction solvents for protein 16 and the thermal stability solvents of protein. 19 Specifically, Dai et al (2013) 20 declared that natural deep eutectic solvents formed by organic acid and sugar was a green approach for the dissolution of wheat proteins.…”

Section: Introductionmentioning

confidence: 99%

“…Liu et al (2020) prepared high freeze–thaw stability of wheat gluten-based emulsions by incorporating DESs, indicating a potential hydrocolloid for wheat gluten after the treatment of incorporated DESs,which is the first available food production application reported concerning wheat gluten after the treatment of DESs or NADESs. So far, NADESs have been applied extensively in many fields such as separation and extraction technique, biocatalysis, organic synthesis, and electrochemistry . Particularly, NADESs have been widely applied as the assisted extraction solvents for protein and the thermal stability solvents of protein .…”

Section: Introductionmentioning

confidence: 99%

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Highly Efficient Deamidation of Wheat Gluten by Glucose-Citric Acid-Based Natural Deep Eutectic Solvent: A Potential Effective Reaction Media

Cao

Zheng

Chen

et al. 2021

J. Agric. Food Chem.

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An efficient technique using citric acid and glucose based natural deep eutectic solvent (G-C-NADES) was developed to obtain ultrahigh deamidated wheat gluten (UDWG) (deamidation degree (DD) > 90%). FTIR and 1 H NMR indicated intensive hydrogen bonds (HBs) in G-C-NADES supermolecules. Quantum chemical calculations and molecular dynamic simulations demonstrated that 10 wt % diluted G-C-NADES still had a myriad of HBs. Physicochemical results showed UDWG had DD up to 92.45% after G-C-NADES deamidation, that is, 22% higher than citric-acid-DWG with a weak degree of hydrolysis (1.75%). Conformational characterization demonstrated the obvious conversion from α-helix to β-sheet via FTIR, the least amount of disulfide bonds by Raman spectra, and more exposure of tryptophan residues by fluorescence measurement for UDWG. It is proven that enhanced accessible conformation of WG reached with HBs of G-C-NADESs could contribute to the improvement on nucleophilic attack of deamidation, declaring that G-C-NADES might be a potential solvent for obtaining an ultrahigh deamidation for WG to successfully guarantee the safety of wheat gluten based cereal food regarding to lowering its allergy.

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“…Up to date, several enzymes such as lipases, proteases and epoxide hydrolases have shown great catalytic performance in DES, demonstrating their potential to replace ILs and/or organic solvents in biocatalytic reactions. Nevertheless, some questions remains to answer and an in-depth understanding on how DESs can activate and stabilize enzymes or how the biocatalysis products may actually be separated from DES will promote the application of DESs in biocatalysis to laboratory or industrial scale 8,13 .…”

Section: Scaled Up?mentioning

confidence: 99%

How do we drive deep eutectic systems towards an industrial reality?

Paiva

Matias

Duarte

2018

Current Opinion in Green and Sustainable Chemistry

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Deep eutectic systems (DES) have received considerable attention in the past 5 years of research.Up to 2013 little had been explored over these systems both in which concerns fundamentals and applications. The definition of a deep eutectic system is still controversial and in this manuscript we highlight the different definitions proposed in the literature and discuss what, in our opinion, should be pursued in order to have an agreement in the scientific community studying this field.From the definition of DES to its applications also interesting changes have been observed in the topics published. From electrochemistry to newer applications, such as cryopreservation, the field is evolving as new outcomes on DES properties are unraveled. We herein present and discuss new trends on DES research and present some perspectives on what we consider to be the most promising applications of DES at industrial scale.

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Deep Eutectic Solvents Enable the Enhanced Production of n‐3 PUFA‐Enriched Triacylglycerols

Cited by 8 publications

References 30 publications

Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents

Immobilized MAS1 Lipase-catalyzed Synthesis of n-3 PUFA-rich Triacylglycerols in Deep Eutectic Solvents

Highly Efficient Deamidation of Wheat Gluten by Glucose-Citric Acid-Based Natural Deep Eutectic Solvent: A Potential Effective Reaction Media

How do we drive deep eutectic systems towards an industrial reality?

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