Molecular Catalysis
·
2025
·
IF 4.9
Duan Zhou,Mouming Zhao,Xiaorong Zhong,Xuefeng Chen,Ning Liu,Daoming Li
Diacylglycerol (DAG) has extensive applications in many fields due to its health benefits and amphiphilic property. Herein, enzymatic esterification of oleic acid and glycerol in natural deep eutectic solvents (NADESs) was employed to synthesize DAG. Firstly, Novozym 435 and choline chloride: glycerol (ChCl:Gly) system were selected as the most appropriate immobilized lipase and NADES for DAG synthesis. Subsequently, the reaction conditions of Novozym 435-catalyzed esterification in ChCl:Gly system were optimized, and the content of DAG reached as high as 67.08 wt % ± 0.79 wt % under the optimal conditions (molar ratio of oleic acid to glycerol of 1:4, reaction temperature of 50 °C, enzyme dosage of 4 wt % with respect to the total weight of substrates, reaction time of 7 h). At last, the reasons why ChCl:Gly could induce a higher DAG content were explored from thermodynamics, water activity and reaction interface. The results showed that ChCl:Gly system could absorb the generated water during esterification and increase the reaction interface, thus beneficial to DAG synthesis. Moreover, the activation energy of DAG production (55.36 kJ/mol) was significantly lower than that of monoacylglycerol (MAG) production (62.60 kJ/mol), leading to the priority of DAG production. Briefly, the multiple beneficial effects of NADESs on lipase-catalyzed esterification collectively contributed to an enhancement of DAG content in esterification products.
研究领域:
生物化学
·
食品科学
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DOI
高影响因子
BIOPROCESS AND BIOSYSTEMS ENGINEERING
·
2015
·Vol. 38
·期 11
·2053-2061
·
IF 1.997
Zeng Chao-Xi,Qi Sui-Jian,Xin Rui-Pu,Yang Bo,Wang Yong-Hua
In this study, enzymatic selective esterification of oleic acid with glycerol based on deep eutectic solvent acting as substrate and solvent was studied. As choline chloride (ChCl) or betaine can effectively change the chemical reaction characteristics of glycerol when they are mixed with a certain molar ratio of glycerol, several factors crucial to the lipase catalytic esterification of glycerol with oleic acid was investigated. Results showed that, betaine had more moderate effects than ChCl on the lipase, and water content had an important influence of the esterification and the enzyme selectivity. Significant changes of the glyceride compositions and enzyme selectivity were found in ChCl adding system compared with pure glycerol system; optimum accumulation of DAG especially 1,3-DAG because of the eutectic effect of ChCl was found in this system. Furthermore, in a model 1,3-DAG esterification synthesis system catalyzed by Novozym 435, high content (42.9 mol%) of the 1,3-DAG could be obtained in ChCl adding system within 1 h.
研究领域:
生物化学
·
食品科学
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DOI
PubMed
高影响因子
RSC Advances
·
2021
·Vol. 11
·期 25
·15054-15059
·
IF 3.361
Miaojia Song,Xiaohui Di,Yu Zhang,Yongming Sun,Zhongming Wang,Zhenhong Yuan,Ying Guo
As an important bio-based chemical, methyl levulinate (ML) can be produced via enzymatic esterification of levulinic acid with methanol. A kinetic model is developed in this work based on the law of mass action and reaction reversibility, to investigate the effect of enzyme loading, alcohol/acid ratio and temperature on ML yield. Data analysis shows that newly developed binary regression is apparently more persuasive than the commonly used unitary regression. Kinetic study reveals: (1) rate constants of esterification/hydrolysis increase with increasing enzyme loading, while their ratio (equilibrium constant) remains invariant. (2) Methanol has no toxicity towards lipase, and hence, neither the rate constants of esterification/hydrolysis nor the equilibrium constant are affected by alcohol/acid ratio. (3) Both rate constants of esterification/hydrolysis and the equilibrium constant increase with temperature elevation, and their relationships agree with Arrhenius equation and Van't Hoff equation, respectively. (4) The esterification is endothermic and spontaneous. In total, the application of binary regression analysis for the developed model to study the enzymatic esterification kinetics is quite successful.
研究领域:
生物化学
·
酶工程
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DOI
高影响因子
RSC Advances
·
2023
·Vol. 13
·期 38
·26690-26699
·
IF 3.9
Zhigang Li,Yinglin Fang,Jiawei Yang,Huayong Chen,Bo Yang,Yonghua Wang
A novel two-step enzymatic esterification-hydrolysis method that generates high-purity conjugated linoleic acid (CLA) isomers was developed. CLA was first partially purified by enzymatic esterification and then further purified by efficient, selective enzymatic hydrolysis in a three-liquid-phase system (TLPS). Compared with traditional two-step selective enzymatic esterification, this novel method produced highly pure cis-9, trans-11 (c9,t11)-CLA (96%) with high conversion (approx. 36%) and avoided complicated rehydrolysis and reesterification steps. The catalytic efficiency and selectivity of CLA ester enzymatic hydrolysis was greatly improved with TLPSs, as high-speed stirring provided a larger interface area for the reaction and product inhibition was effectively reduced by extraction of the product into other phases. Furthermore, the enzyme-enriched phase (liquid immobilization support) was effectively and economically reused more than 8 times because it contained more than 90% of the concentrated enzyme. Therefore, this novel enzymatic esterification-hydrolysis method can be considered ideal to produce high-purity fatty acid monomers.
研究领域:
食品科学
·
生物化学
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DOI
PubMed
高影响因子
Biofuels Bioproducts & Biorefining-Biofpr
·
2021
·Vol. 16
·期 1
·193-203
·
IF 4.102
Miaojia Song,Jianping Lu,Yu Zhang,Yongming Sun,Zhenhong Yuan,Zhongming Wang
Furfural (FF) is an important bio-based platform compound derived from lignocellulose. It can be converted into many industrially valuable chemicals, a typical one being methyl-2-furoate (MF). At present, MF production depends largely on vigorous one-step chemical catalysis (oxidative esterification), in which expensive catalysts (precious metals) and a high temperature (60–120 °C) are required. To reduce the costs of this procedure, a mild, green, and cheap chemoenzymatic process is proposed where FF is initially chemically oxidized to furoic acid (FA), and then FA is enzymatically esterified to MF. Neither step requires an expensive catalyst, and both occur at low temperatures (30–50 °C). For the chemical oxidation process, the optimized FA yield of 83.7% was obtained at 40 °C with an FF/BTIC (1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride) molar ratio of 0.18, 10 mL N -methyl pyrrolidone, and 0.1 MPa oxygen pressure. For the enzymatic esterification, the optimized MF yield reached 80.6% at 50 °C with 50 mg•mL −1 enzyme loading and an alcohol/acid ratio of 7:1. Kinetic studies demonstrated the oxidation to be a sixth-order reaction, and the esterification to be an endothermic reaction. For both oxidation and esterification reactions, the relationship between the rate constant and temperature agreed well with the Arrhenius equation. For esterification, the relationship between the equilibrium constant and the temperature also agreed with the Van't Hoff equation. A 67.5% MF yield was obtained when sequential oxidation and esterification were initiated from FF. The development of chemoenzymatic processes for MF production from FF is effective and has potential value in decreasing the production cost of MF. © 2021 Society of Chemical Industry and John Wiley & Sons, Ltd
研究领域:
化学工程
·
生物技术
·
绿色化学
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DOI
高影响因子
Antioxidants
·
2022
·Vol. 11
·期 10
·1906
·
IF 7.675
Shanxiu Ming,Shuyi Li,Zhe Chen,Xujun Chen,Feifei Wang,Shaonan Deng,Krystian Marszałek,Zhenzhou Zhu,Wenxiang Zhang,Francisco J. Barba
Lipophilization is a promising way to improve the bioavailability of flavonoids. However, the traditional enzymatic esterification methods are time-consuming, and present low yields and purity. Herein, a novel membrane-based lipophilization technology—bioinspired lipase immobilized membranes (BLIMs), including CAL-B@PES, CAL-B@PDA/PES and GA/CAL-B@PDA/PES— were fabricated to improve the antioxidant flavanone glycoside hesperidin lipophilization. Via reverse filtration, PDA coating and GA crosslinking,Candida antarcticalipase B (CAL-B) was stably immobilized on membrane to fabricate BLIMs. Among the three BLIMs, GA/CAL-B@PDA/PES had the greatest enzyme activity and enzyme loading, the strongest tolerance of changes in external environmental conditions (temperatures, pH, heating time, storage time and numbers of cycles) and the highest hesperidin esterification efficiency. Moreover, the optimal operating condition for GA/CAL-B@PDA/PES fabrication was the CAL-B concentration of 0.36 mg/mL, operation pressure of 2 bar, GA concentration of 5% and crosslinking time of 1 h. Afterwards, the hesperidin esterification process did not affect the micromorphology of BLIM, but clearly improved the BLIM permeability and esterified product efficiency. The present study reveals the fabrication mechanism of BLIMs and offers insights into the optimizing strategy that governs the membrane-based lipophilization technology process.Keywords:Candida antarcticalipase B;enzymatic esterification;membrane separation;hesperidin lipophilization;bioinspired lipase immobilized membrane
研究领域:
生物化学
·
食品科学
·
制药工程
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产品关联
DOI
PubMed
高影响因子
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