ENZYME AND MICROBIAL TECHNOLOGY
·
2015
·
IF 2.322
Xuemei Tian,Suoqin Zhang,Liangyu Zheng
The first Novozym 435 lipase-catalyzed Morita–Baylis–Hillman (MBH) reaction with amides as co-catalyst was realized. Results showed that neither Novozym 435 nor amide can independently catalyze the reaction. This co-catalytic system that used a catalytic amount of Novozym 435 with a corresponding amount of amide was established and optimized. The MBH reaction strongly depended on the structure of aldehyde substrate, amide co-catalyst, and reaction additives. The optimized reaction yield (43.4%) was achieved in the Novozym 435-catalyzed MBH reaction of 2, 4-dinitrobenzaldehyde and cyclohexenone with isonicotinamide as co-catalyst and β-cyclodextrin as additive only in 2 days. Although enantioselectivity of Novozym 435 was not found, the results were still significant because an MBH reaction using lipase as biocatalyst was realized for the first time.
研究领域:
生物化学
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催化反应
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DOI
PubMed
高影响因子
MOLECULES
·
2020
·Vol. 25
·期 3
·687
·
IF 3.267
Wan-Xia Wu,Zi Liu
A series of new hyperbranched aliphatic poly(β-thioether ester)s were prepared by the enzymatic ring-opening polycondensation of 1,4-oxathiepan-7-one (OTO) and AB2/ABB’ comonomer with acid-labile β-thiopropionate groups. Two kinds of comonomers, methyl 3-((3-hydroxy-2-(hydroxymethyl)propyl)thio)propanoate (HHTP) and methyl 3-((2,3-dihydroxypropyl)thio)propanoate (DHTP), with different primary alcohols and secondary alcohols, were synthesized by thiol–ene click chemistry and thiol-ene Michael addition, respectively. Immobilized lipase B fromCandida antarctica(CALB), Novozym 435, was used as the catalyst. The random copolymers were characterized by1H-NMR,13C-NMR, GPC, TGA, and DSC. All branched copolyesters had high molecular weights over 15,000 Da with narrow polydispersities in the range of 1.75–2.01 and were amorphous polymers. Their degradation properties under acidic conditions were also studied in vitro. The polymeric nanoparticles of hyperbranched poly(β-thioether ester)s were successfully obtained and showed good oxidation-responsive properties, indicating their potential for biomedical applications.Keywords:Novozym 435;poly(β-thioether ester);hyperbranched;acid degradation;oxidation response
研究领域:
高分子化学
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生物材料
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酶催化
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DOI
PubMed
高影响因子
Molecular Catalysis
·
2023
·
IF 4.6
Qianrui Zhao,Xi Zhang,Meng Zhou,Miao Lai,Dingxia Zhou,Yake Wang,Fang Liu,Mingqin Zhao
A new method for rapid synthesis of pyridine esters without stirring based on Novozym 435 catalysis had been reported, which was from pyridine methanols and vinyl esters. Based on single factor experiment, the optimization of the enzymatic transesterification was received by response surface methodology (RSM). The high yield of 82% was still reached when Novozym 435 had been recycled 12 times. Under optimal conditions, a total of 22 pyridine esters were synthesized. The kinetic model of Novozym 435-catalyzed transesterification of vinyl acetate with 3-pyridinemethanol was established by enzymatic assay. It was discovered that the reaction followed the Ping-Pong Bi-Bi mechanism, and 3-pyridinemethanol inhibited the reaction. Gas chromatography-mass spectrometry-olfactometry (GC–MS-O) was used to analyze the synthesized pyridine esters, of which pyridin-3-ylmethylhexanoate ( 3e ), pyridin-3-ylmethylcinnamate ( 3i ), and 2-(pyridin-2-yl)ethyl acetate (3 s) possessed strong and excellent aromas. These three flavor compounds ( 3e, 3i and 3 s) were found to have good stability at the specified temperature by thermogravimetric (TG) analysis.
研究领域:
生物化学
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酶工程
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食品科学
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DOI
高影响因子
CHIRALITY
·
2018
·Vol. 30
·期 11
·1225-1232
·
IF 1.833
Yinjun Zhang,Feifei Cheng,Hongde Yan,Jianyong Zheng,Zhao Wang
The kinetic resolution of (R,S)-1-(4-chlorophenyl)ethylamine was accomplished using a commercial lipase from Candida antarctica (Novozym 435). The performance of this lipase was investigated for the enantioselective amidation of (R,S)-1-(4-chlorophenyl)ethylamine, leaving the target product (S)-1-(4-chlorophenyl)ethylamine in its unreacted form. The effects of various types of solvents and an acyl donor, the molar ratio of the substrate to the acyl donor, and the reaction temperature were studied. The optimum reaction conditions were found to result in amidation with methyl 2-tetrahydrofuroate at 40°C in methyl tert-butyl ether, with a substrate/acyl donor molar ratio of 1:2.4. The conversion rate of (R,S)-1-(4-chlorophenyl)ethylamine was 52%, with an enantiomeric excess of 99% towards the unreacted substrate in a reaction time of 22 hours. Finally, using optically pure (S)-1-(4-chlorophenyl)ethylamine as the raw material, the chemical synthesis of (S)-N-(1-(4-chlorphenyl)ethyl)-2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)acetamide, a novel triazolopyrimidine herbicide, was achieved, and the total yield and purity were 83.5% and 95.3%, respectively.
研究领域:
生物化学
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有机合成
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酶工程
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DOI
PubMed
高影响因子
BIOMACROMOLECULES
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2021
·
IF 6.988
Yu Zhang,Bo Xia,Yanyan Li,Xianfu Lin,Qi Wu
The synthesis of optically pure polymers is one of the most challenging tasks in polymer chemistry. Herein, Novozym 435 (Lipase B from Candida antarctica, immobilized on Lewatit VP OC 1600)-catalyzed polycondensation between d-/l-aspartic acid (Asp) diester and diols for the preparation of helical chiral polyesters was reported. Compared with d-Asp diesters, the fast-reacting l-Asp diesters easily reacted with diols to provide a series of chiral polyesters containing N-substitutional l-Asp repeating units. Besides amino acid configuration, N-substituent side chains and the chain length of diols were also investigated and optimized. It was found that bulky acyl N-substitutional groups like N-Boc and N-Cbz were more favorable for this polymerization than small ones probably due to competitively binding of these small acyl groups into the active site of Novozym 435. The highest molecular weight can reach up to 39.5 × 103 g/mol (Mw,Đ = 1.64). Moreover, the slow-reacting d-Asp diesters were also successfully polymerized by modifying the substrate structure to create a “nonchiral” condensation environment artificially. These enantiocomplementary chiral polyesters are thermally stable and have specific helical structures, which was confirmed by circular dichroism (CD) spectra, scanning electron microscope (SEM), and molecular calculation.
研究领域:
高分子化学
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生物催化
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材料科学
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DOI
高影响因子
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
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食品科学
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产品关联
DOI
高影响因子
Heliyon
·
2024
·
IF 3.4
Longxin Wang,Qianrui Zhao,Guangpeng Wu,Pengze Wang,Meng Zhou,Zhiyong Wu,Miao Lai,Mingqin Zhao
An efficient method was discovered for catalyzing the esterification under air using Novozym 435 to obtain pyridine esters. The following conditions were found to be optimal: 60 mg of Novozyme 435, 5.0 mL of n-hexane, a molar ratio of 2:1 for nicotinic acids (0.4 mmol) to alcohols (0.2 mmol), 0.25 g of molecular sieve 3A, a revolution speed of 150 rpm, a reaction temperature of 50 °C, and reaction time of 48 h. Under nine cycles of Novozym 435, the 80 % yield was consistently obtained. Optimum conditions were used to synthesize 23 pyridine esters, including five novel compounds. Among them, gas chromatography-mass spectrometry-olfactometry (GC-MS-O) showed phenethyl nicotinate ( 3g ), ( E )-hex-4-en-1-yl nicotinate ( 3m ), and octyl nicotinate ( 3n ) possessed strong aromas. Thermogravimetric analysis (TG) revealed that the compounds 3g , 3m and 3n exhibited stability at the specified temperature. This finding provides theoretical support for adding pyridine esters fragrance to high-temperature processed food.
研究领域:
有机化学
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生物催化
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食品科学
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产品关联
DOI
PubMed
高影响因子
ULTRASONICS SONOCHEMISTRY
·
2017
·
IF 4.218
Chunfang Xu,Haiping Zhang,Jie Shi,Mingming Zheng,Xia Xiang,Fenghong Huang,Junyong Xiao
Monoglyceryl phenolic acids (MPAs) were known as the natural hydrophilic antioxidants which could be used in different fields such as food, pharmaceutical, cosmetic etc. A novel enzymatic route of MPAs synthesis by the alcoholysis of phenolic acid ethyl esters with glycerol under ultrasound irradiation in solvent free system was developed. Optimization of reaction parameters shows that a high conversion of above 97.4% can be obtained under the following conditions: phenolic acid ethyl esters to glycerol molar ratio of 1:10, with 6% catalyst (Novozym 435), at 60 °C and 200 rpm, with ultrasound input of 250 W, at 20 kHz frequency. Compared to the conventional stirring method, the activation energy for phenolic acid ethyl esters conversion was decreased from 65.0 kJ/mol to 32.1 kJ/mol under ultrasound promotion; the apparent kinetic constant (V m /K m ) increased above 1.2-folds; the lipase amount decreased to 50%; the time required for the maximum conversion reduced up to 3-folds without damaging the lipase activity, which is the fastest report for enzymatic synthesis of MPAs.
研究领域:
生物化学
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食品科学
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制药工程
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DOI
PubMed
高影响因子
RSC Advances
·
2013
·Vol. 4
·期 14
·7013-7018
·
IF 2.562
Yaoliang Zhou,Qiuyan Jin,Zhanyang Gao,Hongtao Guo,Haibo Zhang,Xiaohai Zhou
We have successfully developed an easy and efficient bioprocess for asymmetric organic carbonate synthesis by performing Novozym 435 mediated esterification of DMC and alcohols in this work. Under the optimized conditions (60 °C, molar ratio of alcohol to DMC 1 : 12), the highest yield of carbonate can reach 95.6%. An additional advantage of the new process is the fact that 90% of the original activity of the enzyme is retained after being recycled nine times. Consequently it has potential as a useful enzyme-catalyzed process for the industrial production of asymmetric organic carbonates.
研究领域:
生物化学
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绿色化学
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工业酶学
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DOI
高影响因子
JOURNAL OF BIOTECHNOLOGY
·
2013
·
IF 3.183
Peiliang Xiao,Suoqin Zhang,Huayu Ma,Aijun Zhang,Xiaoli Lv,Liangyu Zheng
In this study, a new method was developed to prepare enantiopure caffeic acid amides by enzyme-catalyzed asymmetric aminolysis reaction. Methoxymethyl chloride (MOMCl) was first introduced as a protective and esterified reagent to obtain the MOM-protected caffeic acid MOM ester 1d . Aminolysis reaction occurred between 1d and ( R , S )-α-phenylethylamine in the presence of an immobilized lipase ( Novozym 435) from Candida antarctica . Compared with the methyl-protected caffeic acid methyl ester 1c , 1d as substrate improved the lipase-catalyzed reaction rate by 5.5-fold. After Novozym 435-catalyzed aminolysis reaction was established, we evaluated the effects of synthesis parameters on the catalytic activity and enantioselectivity of Novozym 435. A reaction conversion rate of 25.5% and an E value of >100 were achieved under the following optimum conditions: reaction solvent, anhydrous isooctane; reaction temperature, 70 °C; reaction time, 24 h; ester-to-amine substrate molar ratio, 1:40; and enzyme additive amount, 40 mg. Kinetic and thermodynamic analyses were conducted to determine the main factors affecting enantiomeric discrimination. Novozym 435 still showed 80% of its initial activity after recycling five times. Highly optically pure caffeic acid amides with an enantiomeric excess of 98.5% were finally obtained by HCl deprotection. The established enzyme-catalyzed asymmetric aminolysis method in this study might be used to prepare other caffeic acid amides.
研究领域:
有机化学
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生物催化
·
药物合成
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产品关联
DOI
PubMed
高影响因子
GREEN CHEMISTRY
·
2020
·Vol. 22
·期 6
·1944-1951
·
IF 9.48
Anlian Zhu,Wanlu Feng,Zhiyong Li,Shuang Cheng,Qianhan Chen,Dongshuang Fan,Yuanyang Guo,Lingjun Li,Jianji Wang
The great challenges of modern industry and the environment make it important to develop sustainable energy resources with low cost. In this work, a cleaner enzymatic procedure for biodiesel production was developed through the utilization of a biocompatible and hydrophilic ionic liquid [Choline][H2PO4]. This ionic liquid can be synthesized from cheap raw materials through simple neutralization procedures, and it has been proved to be well biocompatible. The utilization of this ionic liquid in Novozym 435 catalyzed biodiesel production makes the reaction and work-up procedures very simple, because its hydrophilicity can lead to the implementation of a pseudo homogeneous reaction and then heterogeneous separation. Various oil resources such as triolein, sunflower oil and castor oil can all be converted to biodiesels with high yields. After the completion of reaction, both the ionic liquid and Novozym 435 can be recycled and reutilized for at least five cycles without a significant activity decrease. In addition, this reaction system can be conveniently scaled up to the multi-gram level with high efficiency and feasible separation. Overall, the above mentioned benefits make this ionic liquid based enzymatic system cleaner for the production of biodiesel and promising for further industrial applications.
研究领域:
化学工程
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环境科学
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生物技术
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）