CHEMICAL ENGINEERING JOURNAL
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2021
·
IF 13.273
Liqin Zhou,Kungang Chai,Xingdong Yao,Hongbing Ji
It is highly desirable to design and fabricate porous bio-based adsorbent for efficient and selective recovery of acetophenone (AP) and 1-phenylethanol (PE) from the effluent of propylene oxide and styrene monomer co-production (PO/SM) process. Herein, using cassava starch as the starting material, starch-graft-styrene hypercrosslinked polymers (SSHCPs) were designed and synthesized facilely by starch-graft-styrene copolymerization and subsequent crosslinking via a Friedel-Crafts alkylation route. SSHCP-3 (knitted by 4,4′-bis-(chloromethyl)-1,1′-biphenyl) shows high BET surface area (818 m 2 ·g −1 ), large pore volume, and high thermal stability, making it a highly efficient adsorbent for removal of aromatic pollutants from water. SSHCP-3 showed high uptake for AP (2.82 mmol·g −1 ) and selectivity (4.95) of AP over PE in binary-solute adsorption experiments. Spectral studies and theoretical calculation demonstrated that AP and PE uptake could occur at glucose units and benzene moiety via van der Waals interaction and π-π stacking interactions. SSHCP-3 also showed excellent adsorption efficiency of AP (93.6%) and PE (74.4%) in the wastewater discharged from PO/SM process. These results demonstrated that transforming styrene and starch to bio-based hypercrosslinked polymers provides an environmentally friendly and attractive strategy for recovery of AP and PE in practical application.
研究领域:
环境科学
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材料科学
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化学工程
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DOI
高影响因子
FOOD CHEMISTRY
·
2018
·
IF 4.946
Ying Zhou,Qiyuan Peng,Lanting Zeng,Jinchi Tang,Jianlong Li,Fang Dong,Ziyin Yang
After tea leaves, tea ( Camellia sinensis ) flowers are becoming a second tea plant resource because they contain not only functional metabolites similar to those found in tea leaves, but also predominant amounts of functional metabolites that only occur in tea leaves in small amounts. 1-Phenylethanol (1PE) is a predominant aroma compound found in tea flowers. A 1PE synthase in tea flowers was isolated, functionally characterized, and shown to have the highest catalytic efficiency for the conversion of acetophenone (AP). To determine why 1PE accumulates more in tea flowers than other plants, we compared their 1PE contents and used a stable isotope labeling method to elucidate the 1PE biosynthetic route. Supplementation with [ 2 H 8 ] l -phenylalanine and [ 2 H 5 ]AP suggested that most plants containing the enzyme/gene catalyzed the conversion of AP to 1PE. Furthermore, the availability of AP derived from l -phenylalanine was responsible for the difference in 1PE accumulation between tea flowers and other plants.
研究领域:
植物学
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生物化学
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植物代谢
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DOI
PubMed
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
·
2024
·
IF 8.1
Yanyan Xing,Mengke Tian,Ruoman Ji,Ting Wang,Xiaohong Hou
The immobilization of bovine serum albumin (BSA) with high efficiency, good reproducibility and stability for chiral separation has attracted much attention in the medicinal field. BSA was immobilized into MIL-101(Cr) by three ways for efficient chiral separation in this research. MIL-101(Cr)@BSA was firstly prepared by adsorption, NH 2 -MIL-101(Cr) ⊂ BSA by direct bonding, and NH 2 -MIL-101(Cr) ⊂ Glu ⊂ BSA by glutaraldehyde crosslinking bonding. Compared to the other two materials, NH 2 -MIL-101(Cr) ⊂ BSA as a new enantioselective separator, with the most BSA loading rate of 437.6 mg g −1 exhibited excellent chiral separation performances and succeeded in realizing a complete chiral separation of racemic 1–phenylethanol within 14 s. It was found that the NH 2 -MIL-101(Cr) ⊂ BSA was more strongly bound to R -1-phenylethanol and the ee value could reach 100 % when the material was added in three batches. The different interactions between BSA and racemates mainly including hydrogen bonding, hydrophobic interaction and π-π interaction were revealed by the molecular docking studies, especially hydrogen bonding, accounting for the observed selective chiral recognition capacity of racemic 1–phenylethanol of NH 2 -MIL-101(Cr) ⊂ BSA. Moreover, both of NH 2 -MIL-101(Cr) ⊂ BSA and NH 2 -MIL-101(Cr) ⊂ Glu ⊂ BSA showed excellent stability and reusability. This combination of theory and experiment provided a clearer basis for other researchers to have different requirements for protein immobilization, and provided new ideas and methods for the development of chiral selectors.
研究领域:
生物化学
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材料科学
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医药工程
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DOI
高影响因子
Catalysts
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2018
·Vol. 8
·期 1
·13
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IF 3.465
Li Xu,Guli Cui,Caixia Ke,Yanli Fan,Yunjun Yan
A kind of pH-responsive particle was synthesized using modified pullulan polysaccharide. The synthesized particle possessed a series of merits, such as good dispersity, chemical stability and variability of particle size, making it a suitable carrier for enzyme immobilization. Then,Burkholderia cepacialipase (BCL), a promising biocatalyst in transesterification reaction, was immobilized on the synthesized particle. The highest catalytic activity and immobilization efficiency were achieved at pH 6.5 because the particle size was obviously enlarged and correspondingly the adsorption surface for BCL was significantly increased. The immobilization enzyme loading was further optimized, and the derivative lipase was applied in chiral resolution. Under the optimal reaction conditions, the immobilized BCL showed a very good performance and significantly shortened the reaction equilibrium time from 30 h of the free lipase to 2 h with a conversion rate of 50.0% andeesat 99.2%. The immobilized lipase also exhibited good operational stability; after being used for 10 cycles, it still retained over 80% of its original activity. Moreover, it could keep more than 80% activity after storage for 20 days at room temperature in a dry environment. In addition, to learn the potential mechanism, the morphology of the particles and the immobilized lipase were both characterized with a scanning electron microscope and confocal laser scanning microscopy. It was found that the enlarged spherical surface of the particle in low pH values probably led to high immobilized efficiency, resulting in the improvement of enantioselectivity activity in chiral resolution.Keywords:immobilization;Burkholderia cepacialipase;chiral resolution;1-phenylethanol;pullulan
研究领域:
生物化学
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酶工程
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DOI
高影响因子
RSC Advances
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2017
·Vol. 7
·期 51
·32336-32343
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IF 3.108
Ying Zhou,Lanting Zeng,Yinyin Liao,Fang Dong,Qiyuan Peng,Jianlong Li,Jinchi Tang,Naoharu Watanabe,Ziyin Yang
Insect attacks change the quantity of volatiles emitted from plants, but little is known about the effects on the volatiles' stereochemical configurations. 1-Phenylethanol (1PE) is a major internal volatile of tea (Camellia sinensis) flowers. In the present study, insect-damaged C. sinensis flowers in the field emitted a different (R)-/(S)-1PE pattern than that emitted from undamaged flowers. Laboratory experiments showed that changes in the (R)-/(S)-1PE ratio were caused by treatments with Thrips hawaiiensis (Morgan), a pest of cut flowers and vegetable crops. These treatments led to an increase in jasmonic acid (JA) through the activation of allene oxide synthase, which is involved in JA biosynthesis. Exposing flowers to exogenous JA induced an (R)-/(S)-1PE emission pattern that was similar to that induced by a T. hawaiiensis attack, suggesting that JA was involved in the changes in the stereochemical configuration of 1PE emitted from the flowers after insect treatments. This study provides new insights into the involvement of volatiles in interactions between plants and insects, showing that not only the quantity but also the stereochemical configuration of plant volatiles is affected by insects.
研究领域:
植物学
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植物-昆虫互作
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化学生态学
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产品关联
DOI
PubMed
高影响因子
3 Biotech
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2019
·Vol. 9
·期 7
·1-9
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IF 1.786
Yan Hong De,Guo Bing Han,Wang Zhao,Qian Jun Qing
The lipase from Aspergillus oryzae was modified with a surfactant and then observed to exhibit high catalytic efficiency and enantioselectivity for the kinetic resolution of ( RS )-1-phenylethanol. The influential factors of the modified-lipase preparation were investigated, including the surfactant source, the organic cosolvent, and the buffer pH. The optimum modification conditions were found with a surfactant of polyoxyethylene sorbitan monopalmitate, an organic cosolvent of tetrahydrofuran and a phosphate buffer of pH 7.0. In the transesterification of ( RS )-1-phenylethanol with vinyl acetate, the surfactant-modified lipase showed excellent enantioselectivity for the R -isomer ( E > 200), giving an enantiomeric excess of higher than 99% for ( R )-1-phenylethyl acetate at 46.8% conversion with the reaction time of 2 h at 30 °C. The enzymatic activity had barely altered after 30 days even at 50 °C when it was saved in a powdered state. The results indicated that the modification strategy was useful and highly efficient, and that modified A. oryzae lipase was a promising biocatalyst in the kinetic resolution of ( RS )-1-phenylethanol.
研究领域:
生物化学
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酶工程
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
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2018
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IF 4.946
Ying Zhou,Qiyuan Peng,Ling Zhang,Sihua Cheng,Lanting Zeng,Fang Dong,Ziyin Yang
1-Phenylethanol is a chiral flavor compound that has enantiomers, ( R )- and ( S )-1-phenylethanol, with different flavor properties. Given that isolating these enantiomers from plants is low yielding and costly, enzymatic synthesis presents an alternative approach. However, the genes/enzymes that specifically produce ( R )- and ( S )-1-phenylethanol in plants are unknown. To identify these enzymes in tea ( Camellia sinensis ) flowers, 21 short chain dehydrogenase (SDR) genes were isolated from tea flowers, cloned, and functionally characterized. Several recombinant SDRs in Escherichia coli exhibited activity for converting acetophenone to ( S )-1-phenylethanol (CsSPESs, >99.0%), while only one SDR produced ( R )-1-phenylethanol (CsRPES, 98.6%). A pair of homologue enzymes (CsSPES and CsRPES) showed a strong preference for NADPH cofactor, with optimal enzymatic reaction conditions of 45–55 °C and pH 8.0. Identification of the tea flower-derived gene responsible for specific synthesis of ( R )- and ( S )-1-phenylethanolsuggests enzymatic synthesis of enantiopure 1-phenylethanol is possible using a plant-derived gene.
研究领域:
生物化学
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酶学
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植物科学
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产品关联
DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2022
·
IF 16.744
Ziqi Zhao,Shaokun Liang,Chengjun Kang,Zhaoqiang Zhang,Liqin Zhou,Zhenxia Zhao,Xingzhen Qin,Yushan Pang,Hongbing Ji,Kungang Chai
Adsorption is considered as a promising method to purify the mixed acetophenone (AP) and 1-phenylethanol (1-PE) that are generally difficult to separate. Many efforts have been made to improve the preferential uptake of AP over 1-PE in aqueous phase, but there exists a practical bottleneck associated with their limited aqueous solubility. Herein, we demonstrate unprecedented reversal of selectivity in the organic medium enabled by β-ketoenamine-linked covalent organic frameworks (COFs), which were fabricated successfully by polycondensation between 1,3,5-triformylphloroglucinol (Tp) and diamines. The dependence of selective adsorption ability toward 1-PE on pore size was firstly investigated experimentally, indicating that TpBZ-COF with moderate pore size outperformed other analogues. The adsorption behaviors of 1-PE and AP onto TpBZ-COF were examined systematically. The evaluation results revealed a strong affinity toward 1-PE versus AP as well as excellent stability in recycling experiments. Further, the dynamic breakthrough experiments confirmed the practical application potential and remarkable recyclability. To probe the mechanism and structure–activity relationship, an imine-linked COF possessing similar porous structure was used as a reference for comparison of separation performance both experimentally and theoretically. The occurrence of hydrogen bonding between the hydroxyl of 1-PE and β-ketoenamine-linkage as H-bond acceptor in suitable pore spaces endows TpBZ-COF a fantastic candidate for purifying 1-PE and AP from petrochemical by-products.
研究领域:
化学工程
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材料科学
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产品关联
DOI
高影响因子
CATALYSIS COMMUNICATIONS
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2018
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IF 3.463
Baojiao Gao,Coco Bi
N-hydroxyphthalimide (NHPI) was synchronously synthesized and immobilized on crosslinked polystyrene (CPS) microspheres via a short-cut of polymer reactions, obtaining the heterogenous catalyst. Some compositional catalysts were constituted by CPS-NHPI microspheres and metal salts, and they were used in the oxidation reactions of 1-phenylethanol with molecular oxygen as oxidant. Among four co-catalysts, vanadyl acetacetonate (VO(acac) 2 ), Co(OAc) 2 , CoCl 2 and Mn(OAc) 2 , the catalytic activity of VO(acac) 2 is the best although cobalt and manganese salts are conventional co-catalysts of NHPI. Under mild conditions, CPS-NHPI microspheres in combination with VO(acac) 2 can transform selectively 1-phenylethanol into acethenone with a conversion of 40%.
研究领域:
化学
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催化反应
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DOI
高影响因子
CATALYSIS LETTERS
·
2019
·Vol. 149
·期 11
·2973-2983
·
IF 2.372
Luo Wei,Du Hui-Jun,Bonku Emmanuel Mintah,Hou Ya-Li,Li Ling-Ling,Wang Xiao-Qiang,Yang Zhong-Hua
Abstract Enantiopure alcohols have received much attention due to their widespread use as pharmaceutical intermediates. In the asymmetric biosynthesis of enantiopure alcohols, the excellent performance of carbonyl reductase makes it be the best choice as the biocatalysts. In this work, an alkali-tolerant carbonyl reductase ( Bs CR, encoded by yueD ) from Bacillus subtilis (strain 168) was obtained through gene mining, and successfully heterologously expressed in Escherichia coli with pET-32a. Bs CR showed excellent alkali resistance and even can keep more than 70% of its peak activity after incubation in Tris–HCl buffer at pH 9.0 for 40 h. The Michaelis constants and maximal velocity of the Bs CR to NADPH (A) and ethyl 4-chloroacetoacetate (B) are \(K_{m}^{A}\) = 5.390 × 10 −2 mmol/L, \(K_{m}^{B}\) = 1.855 mmol/L, and \(V_{max}\) = 147.3 μmol·min −1 ·mg −1 , respectively. Applying the E. coli BL21(DE3)/pET-32a-yueD to catalyze asymmetric reduction of ethyl 4-chloroacetoacetate and acetophenone, the yield of S -CHBE reached 89.9% and S -1-phenyl ethanol reached 66.7%, and e.e. of both products reached more than 99%. This work provides a novel CR for asymmetric reduction. Graphic Abstract A carbonyl reductase ( Bs CR) and its gene were identified through gene mining, and overexpressed in Escherichia coli BL21(DE3) for whole-cell biocatalytic asymmetric reduction
研究领域:
生物技术
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生物化学
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药物科学
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酶学
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DOI
高影响因子
BIOCATALYSIS AND BIOTRANSFORMATION
·
2021
·
IF 2.181
Lu Dong,Shujuan Qi,Jianwei Jia,Yun Zhang,Yunfeng Hu
Bacillus sp. DL-1 was isolated from the deep sea of the Western Pacific Ocean and behaved very good resistance to NaCl. The extracellular proteases of Bacillus sp. DL-1 were found to exhibit excellent enantioselectivity for the kinetic resolution of (±)-1-phenylethyl acetate. To improve the stability of the enzyme, the immobilized extracellular proteases were preparated by using 60 g kieselguhr and 1-L crude fermentation broth containing extracellular proteases of Bacillus sp. DL-1, shaking at 25 °C, 200 r/min for 10 h. Every gram of kieselguhr adsorbed 25.7 mg extracellular protease and the enzymatic activity recovery was 79.86%. The immobilized proteases preserved about 35.8% of its activity after 6 repeated uses, which were also used as biocatalyst to asymmetrically hydrolyse (±)-1-phenylethyl acetate for the preparation of (R)-1-phenylethanol and (S)-1-phenylethyl acetate with high optical purities. The effects of pH, temperature, enzyme concentration, substrate concentration, reaction time and additives (metal ions/surfactants) on the resolution were investigated by single factor experiments. Under the optimal reaction conditions (10 mM (±)-1-phenylethyl acetate, 40 mg/mL immobilized extracellular proteases, pH 7.5 (Tris-HCl), 5% (v/v) methanol and 45 °C for 2 h), (R)-1-phenylethanol was generated with the e.e.p being > 97%, and the yield being 53%, respectively. Analogously, under the optimal reaction conditions (10-mM (±)-1-phenylethyl acetate, 360 mg/mL immobilized extracellular proteases, pH 6.0 (PB), 5% (v/v) DMSO and 35 °C for 1.5 h), (S)-1-phenylethyl acetate was generated with the e.e.s being over 99% and the yield being 79%, respectively. Compared with the extracellular proteases from Bacillus sp. DL-2, the immobilized extracellular proteases from Bacillus sp. DL-1 exhibited higher hydrolytic activity and could asymmetrically hydrolyse (±)-1-phenylethyl acetate by using higher substrate concentrations, shorter reaction times to obtain higher yields. Notably, the extracellular proteases of Bacillus sp. DL-1 were demonstrated to behave the same enantio-preference as those of most other reported esterases/lipases. Proteases from deep-sea Bacillus sp. DL-1 are promising biocatalysts for the synthesis of valuable chiral chemicals.
研究领域:
生物催化
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酶学
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微生物学
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有机化学
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产品关联
DOI
高影响因子
APPLIED SURFACE SCIENCE
·
2025
·
IF 6.9
Gankai Huang,Yubao Wang,Yan Du,Qunhua Long,Kungang Chai
Adsorption-based separation of 2-phenylethanol (2-PE) and 1-phenylethanol (1-PE) is crucial yet challenging in the petrochemical industry. In this study, we report that an ultra-micropore aluminum-based metal–organic framework (Al-MOF) (i.e., CAU-23) exhibits higher 2-PE/1-PE selectivity (6.12) and 2-PE adsorption capacity (2.52 mmol g −1 ) in liquid phase compared to its pseudo-isostructural analogue of Al-MOFs, MIL-160 and MOF-303 at 293 K. The micropore diffusion model was employed to give the best fit to the adsorption kinetics of the CAU-23 with a rate achieved higher than MIL-160 and MOF-303. Computational analysis confirmed that 2-PE preferential adsorption stems from CAU-23′s well-matched pore geometry which enables efficient molecular confinement. In combination of inspecting the static adsorption properties of 2-PE and 1-PE onto CAU-23, we found that the superior affinity of CAU-23 toward 2-PE over 1-PE originates from entropy and enthalpy effect. The remarkable 2-PE/1-PE separation capability of CAU-23 was confirmed through breakthrough curve analysis (separation factor ≈ 4). As the first Al-MOF developed for 2-PE/1-PE separation, CAU-23 offers valuable insights into the design of advanced 2-PE-selective adsorbents.
研究领域:
化学工程
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材料科学
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吸附技术
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分离科学
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计算化学
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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）