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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2014 ·Vol. 25 ·期 9 ·1704-1711 · IF 1.253

Production of biodiesel catalyzed by Candida rugosa lipase at interface of w/o microemulsion system

Tan Zhongqin,Fang Miaoli,Du Huan,Song Lelian,Ren Dahai,Tang Xiujuan,Han Xiaoxiang,Liang Xinle

The synthesis between palmitic acid and methanol was carried out in a w/o reverse microemulsion prepared from the mixture of dodecylbenzenesulfonic acid (DBSA)/isooctane/water. Box-Behnken design was adopted to evaluate the effect of significant factors on the methyl palmitate yield and response surface methodology (RSM), which was employed to optimize the process parameters in the esterification. The conditions that showed optimal results for methyl palmitate preparation were: 3.33 w0 ([H2O]/[surfactant]), 4.2 h reaction time, 5:1 methanol/acid molar ratio, and 130 mg g-1 lipase ([lipase]/[acid]) concentration. The following verification experiment obtained a result of 97% in almost total agreement with the expected value (98%). The kinetic constants of the model were determined by experiments at 40 °C with initial concentrations of 0.025-0.25 mol L-1 palmitic acid and 0.025-0.3 mol L-1 methanol in the microemulsion system. The kinetic studies showed that the reaction obeyed the Ping-Pong bi-bi mechanism with inhibition by methanol.

CAS / MDL: 112-39-0
研究领域: 生物化学 · 生物工程
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RSC Advances · 2017 ·Vol. 7 ·期 21 ·12518-12523 · IF 3.108

Chemoenzymatic epoxidation of alkenes with Candida antarctica lipase B and hydrogen peroxide in deep eutectic solvents

Pengfei Zhou,Xuping Wang,Bo Yang,Frank Hollmann,Yonghua Wang

Epoxides are important synthetic intermediates for the synthesis of a broad range of industrial products. This study presents a promising solution to the current limitation of enzyme instability. By using simple deep eutectic solvents such as choline chloride/sorbitol, significant stabilization of the biocatalyst has been achieved leading to more robust reactions while using environmentally more acceptable solvents as compared to ionic liquids.

研究领域: 生物化学 · 绿色化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2025 ·Vol. 105 ·期 7 ·3931-3941 · IF 3.5

Selective synthesis of triacylglycerols by the ADS-17-supported Candida antarctica lipase B through esterification of oleic acid and glycerol

Jiawei Zheng,Qiangyue Zhang,Nanjing Zhong

BACKGROUND Immobilized enzyme possessing both high activity and good selectivity is important in practice. In this study, Candida antarctica lipase B (CALB) was immobilized onto the macroporous resin ADS-17 for triacylglycerol (TAG) synthesis through esterification of oleic acid and glycerol. The reaction conditions were optimized by single-factor study and orthogonal test, and the reusability of the immobilized CALB (CALB@ADS-17) was evaluated. In addition, the mechanism of lipase immobilization was studied and the catalytic mechanism of CALB@ADS-17 was investigated. RESULTS Oleic acid conversion up to 99.20% and TAG content at 91.58 wt% could be obtained under optimal conditions. In addition, the CALB@ADS-17 retained 84.28% of its initial activity after 11 cycles of reuse. The mechanism of lipase immobilization was through hydrophobic adsorption. The relationship between temperature and oleic acid conversion was ln V 0 = 6.3316 − 4.3321/ T , and the activation energy ( E a ) was 36.02 kJ mol −1 . CALB@ADS-17 did not exhibit an obvious interfacial activation phenomenon. Its kinetic behavior can be described by the Michaelis–Menten model, whose kinetic parameters of v max , k cat , K m , K i , and k ca t /K m were 0.01265 μmol L −1 s −1 , 9310.72 s −1 , 0.4907 mmol L −1 , 3.997 mmol L −1 , and 1.90 × 10 4 L mmol −1 s −1 , respectively. CONCLUSION CALB@ADS-17 showed good esterification performance and exhibited good selectivity towards TAG generation. In addition, CALB@ADS-17 exhibited good reusability in esterification reactions and has potential in practical applications. © 2025 Society of Chemical Industry.

研究领域: 生物化学 · 酶工程
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2018 · IF 3.909

Immobilization of Candida antarctica Lipase B onto organically-modified SBA-15 for efficient production of soybean-based mono and diacylglycerols

Yue Li,Nanjing Zhong,Ling-Zhi Cheong,Jianrong Huang,Hongxiao Chen,Shaoyan Lin

In this study, SBA-15 was modified by a series of silane coupling reagents and later used to immobilize Candida antartica lipase B (CALB). The enzymatic properties of the immobilized CALB samples were studied. In addition, the catalytic performance in glycerolysis of soybean oil for diacylglycerols (DAG) production was also investigated. The highest enzymatic activity up to 6100.00 ± 246.41 U/g was observed from the propyl methacrylate group modified SBA-15 supported CALB. No loss of activity was observed from the propyl methacrylate group modified SBA-15 supported CALB, but a higher-than-initial activity was notably found from 3-aminopropyl group and n -octyl group modified SBA-15 supported CALB after a 4-h incubation in air at 70 °C. 1-isocyanatopropane group modified SBA-15 supported CALB exhibited selectivity for DAG production. DAG content up to 61.90 ± 2.38 wt% and a DAG/MAG ratio at 3.11 ± 0.08 was obtained after a 24-h reaction at 60 °C in a solvent-free system.

研究领域: 生物化学 · 酶工程 · 食品科学
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CHINESE CHEMICAL LETTERS · 2016 · IF 1.947

Enzyme-catalyzed direct three-component aza-Diels–Alder reaction using lipase from Candida sp. 99–125

Dong-Hang Yin,Wei Liu,Zhi-Xiang Wang,Xin Huang,Jing Zhang,De-Chun Huang

The direct three-component aza-Diels–Alder reaction was conducted with lipase as a catalyst for the first time. Under the optimized conditions, the aza-Diels–Alder reaction catalyzed by lipase from Candida sp. 99–125 provided the products in moderate to excellent yields. Meanwhile, the endo / exo ratio reached up to 88:12.

研究领域: 生物化学 · 有机合成 · 酶学
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JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC · 2015 · IF 2.128

Improved enzymatic properties of Candida rugosa lipase immobilized on ZnO nanowires/macroporous SiO2 microwave absorbing supports

Chuan-Yang Shang,Wei-Xun Li,Feng Jiang,Rui-Feng Zhang

ZnO nanowires/macroporous SiO 2 composites were used as a new type of microwave absorbing support to immobilize Candida rugosa lipase (CRL). Under microwave irradiation the immobilized lipase was used to catalyze esterification of phytosterol and oleic acid for the synthesis of phytosterol esters. A great improvement of the catalytic activity was found in the systems in which composited ZnO nanowires were present. The microwave absorbing properties of ZnO nanowires have been proved to be helpful for the synergistic effect between microwave irradiation and enzyme catalysis. The immobilized CRL showed higher thermal stability at 55   °C under microwave irradiation than conventional heating. A maximum molar conversion of 95.4% under microwave irradiation was achieved under the optimal condition: 0.1   M phytosterol, 0.2   M oleic acid, water activity ( a w ) of 0.11, reaction temperature at 50   °C and reaction time of 1   h.

研究领域: 生物化学 · 酶工程 · 纳米材料科学
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MATERIALS RESEARCH BULLETIN · 2015 · IF 2.288

Immobilization of Candida rugosa lipase on ZnO nanowires/macroporous silica composites for biocatalytic synthesis of phytosterol esters

Chuan-Yang Shang,Wei-Xun Li,Rui-Feng Zhang

ZnO nanowires were successfully introduced into a macroporous SiO 2 by in-situ hydrothermal growth in 3D pores. The obtained composites were characterized by SEM and XRD, and used as supports to immobilize Candida rugosa lipase (CRL) through adsorption. The high specific surface area (233   m 2 /g) and strong electrostatic interaction resulted that the average loading amount of the composite supports reached 287.2   mg/g. Both adsorption capacity and the activity of the CRL immobilized on the composite supports almost kept unchanged as the samples were soaked in buffer solution for 48   h. The immobilized CRL exhibited better thermal stability, reusability and pH adaptability in comparison to free CRL. The immobilized CRL was used as biocatalyst for the preparation of phytosterol esters by the esterification of phytosterol and oleic acid. A maximum molar conversion of 96.5% was achieved under the optimal condition. After twelve recycles the immobilized lipase could retain 89.9% of its initial activity.

研究领域: 生物化学 · 纳米材料科学 · 酶工程
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Scientific Reports · 2021 ·Vol. 11 ·期 1 ·1-10 · IF 4.38

The influence of the chemical composition of essential oils of Clausena lansium seeds on the growth of Candida strains

Ma Yinzheng,Wang Yuanxiao,Zhou Xia,Yang Heng,Zhang Huixin,Chen Wenhan,Zhang Haiying,Zhang Yunxia,He Xiaowen

Clausena lansium (Lour.) Skeels seeds have been shown to have diverse beneficial medical value due to their unique active components. This study analysed the composition of essential oils (EOs) of C. lansium seeds and investigated their potential antifungal effects against Candida strains . A total of forty-six components were identified in all samples by gas chromatography-mass spectrometry (GC–MS). The main components were sabinene, β -phellandrene and 4-terpineol. Thirteen EOs of C. lansium seeds were classified into three clusters based on their components. Cluster analysis showed that the difference between the tropics and subtropics was the greatest. These EOs and the three main chemicals showed different antifungal activities against five Candida species ( C. albicans , C. tropicalis , C. glabrata , C. krusei and C. parapsilosis ). The antifungal activity against C. glabrata and C. krusei was higher than that against other Candida strains. EOs of C. lansium seeds displayed noteworthy antifungal activity against both sensitive and fluconazole-resistant strains, with inhibition zone diameters in the range of 9.4–23.4 mm. Comprehensive analysis illustrated the importance of sabinene, β -phellandrene and 4-terpineol to antifungal activity, and there may be some synergistic effects with other components. These results represent the first report about the correlation between the chemical composition of EOs of C. lansium seeds and antifungal activity. Taken together, the results obtained provide scientific evidence for the traditional use of C. lansium seeds waste.

研究领域: 植物化学 · 微生物学 · 药理学
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BIOPROCESS AND BIOSYSTEMS ENGINEERING · 2015 ·Vol. 38 ·期 5 ·939-946 · IF 1.997

Enzymatic synthesis of phytosterol esters catalyzed by Candida rugosa lipase in water-in-[Bmim]PF6 microemulsion

Zeng Chaoxi,Qi Suijian,Li Zhigang,Luo Riming,Yang Bo,Wang Yonghua

A water-in-ionic liquid microemulsion ([Bmim]PF 6 /Tween20/H 2 O) was applied as reusable reaction medium to esterify phytosterols with fatty acid by Candida rugosa lipase (CRL) successfully. Two kinds of commercial CRLs, AY30 and AYS which cannot effectively catalyze esterification in conventional reaction system were found effective in the microemulsion system. Effects of reaction parameters on esterification were investigated; results showed that the conversion rate of 87.9 and 95.1 % was obtained in 24 and 48 h of reaction, respectively, under the optimized condition: the molar ratio of water to Tween 20 ( w 0 value) at 5.4, Tween 20 at a concentration of 305 mM, 50 °C,pH 7.4, 10 % of enzyme loading (w/w, with respect to total reactants), and phytosterols/lauric acid molar ratio of 1:2. Moreover, by using n-hexane as the extraction agent, the lipase-encapsulated microemulsion could be reused at least seven times (>168 h) without significant changes in the conversion rate, while achieving a purpose of simple separation and purification.

CAS / MDL: 143-07-7
研究领域: 生物化学 · 酶工程
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BIOCHEMICAL ENGINEERING JOURNAL · 2021 · IF 3.978

Immobilization of Candida rugosa lipase (CRL) on a hierarchical magnetic zeolitic imidazole framework-8 for efficient biocatalysis

Yumei Xiao,Yanxia Chen,Ruowei Lu,Yongchao Wang,Cuijuan Wang

A novel hierarchical magnetic zeolitic imidazolate framework-8 material (Hierarchical mZIF-8) is fabricated by using the cetyltrimethylammonium bromide (CTAB) and L -histidine (His) as templates. Comparing to usual magnetic ZIF-8 (mZIF-8), there are not only micropores (1.1 nm) but also new mesopores (23.3 nm) in hierarchical mZIF-8 material. It is the first time that Candida rugosa lipase (CRL) has been immobilized into hierarchical mZIF-8 with significantly higher enzyme loading capacity than mZIF-8. Furthermore, the temperature stability, pH stability and recycling convenience of immobilized CRL are all enhanced compared with free CRL.

研究领域: 生物化学 · 材料科学 · 酶工程
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Materials Science & Engineering C-Materials for Biological Applications · 2014 · IF 2.736

Improvement of the activation of lipase from Candida rugosa following physical and chemical immobilization on modified mesoporous silica

Chunfeng Wang,Yanjing Li,Guowei Zhou,Xiaojie Jiang,Yunqiang Xu,Zhaosheng Bu

Lipase from Candida rugosa (CRL) was chemically and physically immobilized onto four types of rod-shaped mesoporous silica (RSMS). RSMS prepared using surfactant P123 and poly(ethylene glycol) as co-templates was functionalized with (3-aminopropyl)triethoxysilane (APTES) to obtain P-RSMS by post-synthesis grafting. Tetraethoxysilane was hydrothermally co-condensed with APTES to obtain C-RSMS. A two-step process using APTES and glutaraldehyde was also performed to obtain G-RSMS. The effects of modification methods (including post-synthesis grafting and co-condensation) and glutaraldehyde on the mesoscopic order, interplanar spacing d 100 , cell parameter a 0 , mesoporous structure, and wall thickness of RSMS were studied in detail. Results showed that all samples were mesoporous materials with 2D mesostructures ( p 6 mm ). Pore size and d 100 decreased, whereas the wall thickness increased after different modifications. CRL was used as a model enzyme to determine the effect of physical and chemical adsorption on loading amount and enzymatic activity. The possible mechanism of CRL immobilization on G-RSMS by chemical adsorption was systematically investigated. The chemical immobilization of CRL on G-RSMS increased the loading amount, hydrolytic activity, thermal stability, and reusability. Moreover, immobilized CRL was employed to catalyze the resolution of 2-octanol by esterification with caprylic acid. The enantiomeric excess of 2-octanol was 45.8% when the reaction was catalyzed by G-RSMS-CRL and decreased to about 38%–39% using the physically immobilized CRL, after 48   h of reaction in hexane.

CAS / MDL: 123-96-6
研究领域: 生物化学 · 材料科学
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BIOPROCESS AND BIOSYSTEMS ENGINEERING · 2014 ·Vol. 37 ·期 8 ·1617-1626 · IF 1.823

Chemical modification with functionalized ionic liquids: a novel method to improve the enzymatic properties of Candida rugosa lipase

Hu Yi,Yang Jiao,Jia Ru,Ding Yan,Li Shuang,Huang He

Chemical modification of lysine residues in Candida rugosa lipase (CRL) was carried out using five different functional ionic liquids, and about 15.4–25.0 % of the primary amino groups of lysine were modified. Enzymatic properties of the native and modified CRLs were investigated in olive oil hydrolysis reaction. Improved thermal stability, catalytic activity in organic solvents, and adaptability to temperature and pH changes were achieved compared with the native enzyme. CRL modified by [choline][H 2 PO 4 ] showed the best results, bearing a maximum improvement of 16.7 % in terms of relative activity, 5.2-fold increase in thermostability (after incubation at 45 °C for 5 h), and 2.3-fold increase in activity in strong polar organic solvent (80 % dimethyl sulfoxide) compared with the native enzyme. The results of ultraviolet, circular dichroism and fluorescence spectroscopy suggested that the change of the secondary and tertiary structures of CRL caused by the chemical modification resulted in the enhancement of enzymatic performance. The modification of CRL with functional ionic liquids was proved to be a novel and efficient method for improving the enzymatic properties of CRL.

CAS / MDL: 530-62-1
研究领域: 生物化学 · 酶工程
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