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RSC Advances · 2022 ·Vol. 12 ·期 42 ·27550-27554 · IF 4.036

Dearomative gem-diprenylation of hydroxynaphthalenes by an engineered fungal prenyltransferase

Yuanyuan Xu,Dan Li,Wenxuan Wang,Kangping Xu,Guishan Tan,Jing Li,Shu-Ming Li,Xia Yu

Prenylation usually improves structural diversity and bioactivity in natural products. Unlike the discovered enzymatic gem-diprenylation of mono- and tri-cyclic aromatic systems, the enzymatic approach for gem-diprenylation of bi-cyclic hydroxynaphthalenes is new to science. Here we report an enzymatic example for dearomative C4 gem-diprenylation of α-hydroxynaphthalenes, by the F253G mutant of a fungal prenyltransferase CdpC3PT. Experimental evidence suggests a sequential electrophilic substitution mechanism. We also explained the alteration of catalytic properties on CdpC3PT after mutation on F253 by modeling. This study provides a valuable addition to the synthetic toolkit for compound prenylation and it also contributes to the mechanistic study of prenylating enzymes.

研究领域: 生物化学 · 酶学 · 有机化学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2021 · IF 4.759

Comparison of chromatographic performance of co-grafted silica using octadecene respectively with vinylpyrrolidone, vinylimidazole and vinylpyridine

Chao Fan,Kaijun Quan,Jia Chen,Hongdeng Qiu

Three reversed-phase liquid chromatography (RPLC) stationary phases were obtained by using long-chain 1-octadecene (OD) co-grafted with three short-chain monomers, including N-vinylpyrrolidone (NVP), 1-vinylimidazole (VIm) and 4-vinylpyridine (VPy), respectively (noted as Sil@ODNVP, Sil@ODVIm and Sil@ODVPy). Peak broadening phenomenon in RPLC mode which resulted by short-chain was examined carefully. Compared with Sil@ODNVP, both of Sil@ODVIm and Sil@ODVPy had smaller peak width and higher column efficiency in the separation of 10 polycyclic aromatic hydrocarbons (PAHs), 7 alkyl benzenes, 7 aromatic acids, 7 aromatic esters and 9 phenols. In addition, VPy has the strongest ion exchange capacity than other two short-chains. In this case, we can see that VPy and VIm maybe more suitable to be used as functional monomeric modifiers of new chromatographic stationary phases.

研究领域: 分析化学 · 色谱技术
✓ 已验证 DOI 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2024 · IF 3.3

Controlled and Site-Selective C–H/N–H Alkenylation, Dialkenylation, and Dehydrogenative β-Alkenylation of Various N-Heterocycles

Jin Yan,Suijie Zhong,Xu Chen,Yihuan Luo,Hua Cao,Xiang Liu,Limin Zhao

Here, we report controlled and site-selective C–H alkenylation and dialkenylation of indolizines and pyrrolo[1,2-a]quinolines with β-alkoxyvinyl trifluoromethylketones under simple and practical conditions. Moreover, this direct C–H alkenylation strategy can also be extended to imidazo[1,2-a]pyridines. Notably, without a transition metal and external oxidant, efficient dehydrogenative β-alkenylation of tertiary amines with β-alkoxyvinyl trifluoromethylketones is presented.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI 高影响因子
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FOOD CHEMISTRY · 2021 · IF 7.514

Model studies on the formation of 2-vinylpyrazine and 2-vinyl-6-methylpyrazine in Maillard-type reactions

Yun-Jiao Ma,Xiao-Yuan Wang,Bei-Wei Zhu,Ming Du,Liang Dong,Xiu-Ping Dong,Xian-Bing Xu

Vinylpyrazine compounds are widely present in foods , especially in hot-processed foods, as a class of flavor compounds ; however, their formation mechanism in food systems is still unclear. Therefore, in this study, 2-vinylpyrazine and 2-vinyl-6-methylpyrazine were identified in the Maillard model reaction of d -glucose and glycine. The Maillard model reaction of glucose–glycine was constructed to explore the effects of reaction parameters on vinylpyrazines and the related products. The Maillard reaction of [U- 13 C 6 ] glucose and glycine was established, and alkylpyrazines and formaldehyde were determined via isotope tracing technique as the precursors of vinylpyrazines. The formation of vinylpyrazines was verified by building a model reaction between alkylpyrazines and formaldehyde. The H/D exchange experiment confirmed that the active site of alkylpyrazines was on the methyl group , which was the reaction site for the condensation reaction of alkylpyrazines with formaldehyde. Results suggest that vinylpyrazines are formed by the condensation reaction of alkylpyrazines and formaldehyde.

研究领域: 食品科学 · 化学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF APPLIED POLYMER SCIENCE · 2020 ·Vol. 138 ·期 8 ·49872 · IF 2.52

Preparation of composite anion exchange membranes based on in-situ copolymerization of N-vinyl formamide and divinylbenzene in porous PTFE

Wanjie Luo,Lulu Wang,Ruijiang Feng,Chongfeng Zhao,Jilin Wang,Tianzhou Cai

A series of composite anion exchange membranes was synthesized via in-situ copolymerization of various ratios N-vinyl formamide (NVF) and divinylbenzene (DVB), supported by porous polytetrafluoroethylene (PTFE) polymer matrix, and followed by alkaline hydrolysis, and quaternization of the composite membranes with epoxypropyltrimethylammonium chloride (EPTMAC). FTIR and SEM analyses revealed that the composite membranes were successfully prepared. Moreover, the hydrophilic property of the composite membrane improved by introduction of the quaternized poly(NVF-co-DVB) copolymer. Water uptake, swelling ratio, and conductivity showed upward trends by increase of NVF amount. The copolymer with 95% of NVF showed the highest elongation at break (102%, room temperature) and conductivity (5.15 × 10 −2 S/cm, 80°C). After immersion of the PNDB 95% -N membrane in 5 mol/L NaOH solution for 96 h at room temperature, the conductivity (60°C) of the membrane decreased to 3.99 × 10 −2 S/cm. Moreover, the membrane registered weight loss under 4.5%, caused by degradation of the quaternary ammonium groups in NaOH solution. All in all, in 3 mol/L methanol solutions, the composite membranes showed permeability ranging from 7.6% to 19.7%, if compared to the Nafion®-115 membrane, showing good alcohol resistance.

研究领域: 材料科学 · 化学工程
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2020 · IF 5.162

Substrate specificity change of a flavonoid prenyltransferase AhPT1 induced by metal ion

Jiali Yang,Ting Zhou,Yueming Jiang,Bao Yang

Prenylated flavonoids are good drug candidates due to multiple biological activities and health benefits. Prenyltransferase is an important enzyme involved in the biosynthesis of prenylated flavonoids. In this work, a flavonoid prenyltransferase (AhPT1) from Artocarpus heterophyllus showed an unexpectedly metal ion-induced specificity to flavonoid substrates. AhPT1 could catalyse 6- C -prenylation of genistein when Mg 2+ serving as cofactor. Its catalytic activity to 6-hydroxyflavone was undetectable. However, when Mn 2+ was used instead of Mg 2+ , 5- C -prenylated 6-hydroxyflavone was generated with a high conversion rate. Mn 2+ altered the regiospecificity of AhPT1 and turned it into a 5- C -prenyltransferase. 2′-Hydroxyl could improve the conversion rate of 6-hydroxyflavone, whereas 3′- or 4′-hydroxyl impaired the catalysis efficiency of AhPT1. NQIFDADID174 and DLTDVEGD305 were active motifs involved in substrate binding and catalysis. Asn166, Asp170, Asp174, Asp298, Asp301 and Asp305 in the active center were critical to the prenylation reaction.

研究领域: 生物化学 · 酶学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2021 · IF 4.759

Sustainable hydrophilic ultrasmall carbonaceous spheres modified by click reaction for high-performance polymeric ion chromatographic stationary phase

Yuqing Li,Sha Liu,Qiaoyan Zhang,Wan Gong,Hua Yin,Bo Yang,Luping Qin,Qiming Zhao,Yan Zhu

Novel poly(ethylvinylbenzene-divinylbenzene) (EVB-DVB) agglomerated with ultrasmall carbonaceous spheres (UCSs) anion-exchange packings for ion chromatography (IC) were constructed. Hydrophilic UCSs with mean sizes of 62–98 nm were synthesized in quantity by the polydiallyl dimethyl ammonium chloride aided hydrothermal carbonization of fructose. The green strategy based on the thiol-ene click reaction with cysteamine in aqueous system was first designed for the hyperbranched polyquaternary amine (HPA) grafting of UCSs with negligible damage on their monodispersity. The HPA modified UCSs were evenly distributed on sulfonated EVB-DVB substrate to form one uniform layer of functional nanospheres without observable coagulum. Seven typical anions ( F − , Cl − , NO 2 − , Br − , NO 3 − , SO 4 2- and PO 4 3− ) were baseline separated on constructed packing in 5 min with high efficiencies in the range of 44,800–71,100 plates m   −   1 . The rapid separation of polarizable anions, small organic acids and saccharides could be also accomplished under isocratic elution with competitive peak symmetry and efficiency. Good reproducibility was demonstrated by consecutive injection. Thiosulfate in water reducer was further detected on prepared packing in 4 min with detection limit of 0.04 mg L   −   1 (S/ N  = 3) and good repeatability.

研究领域: 分析化学 · 材料科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2019 · IF 7.65

Preparation and performance of poly(4-vinylpyridine)-b-polysulfone-b-poly(4-vinylpyridine) triblock copolymer/polysulfone blend membrane for separation of palladium (II) from electroplating wastewaters

Yichang Ma,Jianxian Zeng,Yajie Zeng,Hu Zhou,Guoqing Liu,Yuan Liu,Lingwei Zeng,Jian Jian,Zhengqiu Yuan

In order to separate palladium (II) from electroplating wastewaters, poly(4-vinylpyridine)-b-polysulfone-b-poly(4-vinylpyridine) (P4VP-PSF-P4VP) / polysulfone blend membranes were fabricated by combining non-solvent induced phase separation, surface segregation and self-assembly of block copolymer . Amphiphilic P4VP-PSF-P4VP was used as the membrane base material, which was synthesized by introducing the functional monomer of 4-vinylpyridine (4-VP), and polysulfone as the additive. Effects of blend ratio and 4-VP content on membrane performance, such as structure, hydrophilicity, pure water flux and adsorption capacity towards Pd (II), were investigated. The membranes exhibited dense surface structure and low roughness due to surface segregation and self-assembly of P4VP-PSF-P4VP. The presence of 4-VP increased hydrophilicity and water flux of membrane, and it also provided good adsorption capacity towards Pd (II) (up to 103.1 ± 5.15 mg/g). Further, the membrane was used to separate Pd (II) from simulated wastewaters during filtration. It showed good rejection ability and high selectivity towards Pd (II) in co-existence of Cu (II) and Ni (II), and selectivity coefficients of Pd/Cu and Pd/Ni are 41.9 ± 1.88 and 97.8 ± 4.32, respectively. In filtration process of actual electroplating wastewater, the membrane also exhibited excellent rejection performance (Pd (II) rejection reached up to 96.8 ± 2.71%). Perhaps it is suitable for future practice applications.

研究领域: 材料科学 · 环境科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS · 2022 · IF 3.322

Novel strategy to produce prenylated resveratrol by prenyltransferase iacE and evaluation of neuroprotective mechanisms

Ting Zhou,Bao Yang

Prenylated resveratrols are drug candidates presented in many natural sources. They possess multiple pharmacological activities. Due to the limited abundance in nature and disadvantage of chemical synthesis, it is required to produce prenylated resveratrols by biological strategy. In this work, a prenyltransferase iacE from Pestalotiopsis fici was prepared by heterologous overexpression. It could catalyze 2- C -prenylation of resveratrol efficiently. Dimethylallyl diphosphate (DMAPP) and geranyl diphosphate (GPP) could serve as prenyl donor. Glu97, Thr114 and Tyr413 were proved to be important residues in the active site by site-directed mutagenesis. The product was purified and identified to be 2- C -prenyl resveratrol by NMR . 2- C -prenyl resveratrol exerted neuroprotective activity through inhibiting ROS overproduction and improving the activities of antioxidant enzymes in HT22 cell. The genes involved in antioxidant defense were regulated, including upregulated CAT , SOD2 , NFE2L2 , GPx4 , and downregulated PTGS2 and ACSL4 . These results supplied a novel technique for prenylated resveratrols production.

CAS / MDL: 501-36-0
研究领域: 生物技术 · 药理学 · 神经科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Reaction Kinetics Mechanisms and Catalysis · 2023 ·Vol. 136 ·期 2 ·771-786 · IF 1.8

Efficient conversion of vinyltrimethoxysilane to vinyltris(β-methoxyethoxy)silane through economic γ-Al2O3 loaded with K2CO3

Su Haitang,Yang Zhixiu,Xiao Guomin,Gao Lijing,Wei Ruiping,Zhang Jin

A series of cost-effective (X) K 2 CO 3 /γAl 2 O 3 catalysts for efficient conversion of vinyltrimethoxysilane (VTMOS) to vinyltris(β-methoxyethoxy)silane (VTMOEOS) were synthesized. The microstructure and active site of the synthesized catalysts were analyzed by BET, XRD, FT-IR, SEM, and CO 2 -TPD. The results showed that the synthesized catalysts formed K–O–Al strong basic sites while maintaining the original structure, which greatly improved the basic strength of the catalysts. It was found that the 60%K 2 CO 3 /γAl 2 O 3 possessed the highest the catalytic activity under the activation temperature of 600 °C by optimizing the preparation conditions of K 2 CO 3 /γAl 2 O 3 . Moreover, the optimal reaction process conditions were also determined by optimizing the experimental reaction temperature, reaction time, catalyst dosage, and reactant molar ratio under (60%, 600 °C) K 2 CO 3 /γAl 2 O 3 catalysis. Under the optimal reaction conditions, the conversion of VTMOS was 92.5% and the yield of VTMOEOS was 65%. Meanwhile, the 60%K 2 CO 3 /γAl 2 O 3 catalyst was satisfactorily reusable and maintained a high catalytic activity after four cycles of catalytic reactions.

CAS / MDL: 67-68-5 2768-02-7
研究领域: 材料化学 · 催化化学
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EUROPEAN POLYMER JOURNAL · 2023 · IF 6

Exploring anionic homopolymerization and copolymerization of vinyl monomers in deep eutectic solvent

Jintao Li,Mingzu Zhang,Jinlin He,Peihong Ni

Deep eutectic solvent (DES) represents a kind of eutectic mixture made of two or more substances in a certain ratio with a melting point lower than that of either individual component. As a typical green solvent, DES has been used in polymerization reactions such as condensation polymerization, free radical polymerization, electrochemical polymerization, ring-opening polymerization and oxidative polymerization, but little research has been reported in anionic polymerization. In this work, we explored the anionic homopolymerization, random and block copolymerizations of several vinyl monomers in DES, including styrene (St) and its derivatives (ClSt, MeOSt), isoprene (Ip), and 2-vinylpyridine (2VP). The microstructures and molecular weights of (co)polymers were characterized by nuclear magnetic resonance ( 1 H NMR, 13 C NMR), Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography (GPC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), while the thermal properties of the copolymers were investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results showed that the polymerization products with certain molecular weights, favorable yield and molecular weight distribution could be prepared in DES. In addition, the experimental results indicated that DES can be recycled for polymerization and has little effect on the final product. The anionic polymerization with DES as the reaction medium exhibits mild reaction conditions, which reduces the operational difficulty of traditional anionic polymerization and broadens the application scope of active organolithium reagents.

CAS / MDL: 67-48-1 1073-67-2
研究领域: 高分子科学 · 材料科学 · 绿色化学
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Journal of Materials Chemistry C · 2015 ·Vol. 3 ·期 31 ·8066-8073 · IF 4.696

Intense green-light emission from 9,10-bis (4-(1,2,2-triphenylvinyl)styryl)anthracene emitting electroluminescent devices

Shunyu Jin,Yan Tian,Fei Liu,Jun Chen,Shaozhi Deng,Ningsheng Xu

Although 9,10-bis(4-(1,2,2-triphenylvinyl)styryl)anthracene (TPE-An) with excellent aggregation-induced emission (AIE) properties can effectively enhance the luminescence efficiency of light-emitting materials, the practical TPE-An-emitting electroluminescent (EL) devices have not been successfully fabricated until now. In our paper, the energy-band diagram of TPE-An is determined by the combination of ultraviolet-visible (UV-Vis) spectroscopy and cyclic voltammetry (CV) techniques. Subsequently, the space-charge-limited-current (SCLC) method is firstly used to obtain the hole mobility of TPE-An and design a better EL device structure. By calculation, the maximum hole mobility of the 50 nm TPE-An film can arrive at 4.00 × 10−4 cm2 V−1 s−1 at 0.1 MV cm−1 field. Finally, TPE-An-emitting EL devices have been, respectively, fabricated on glass and flexible PET substrates. Both of these two EL devices exhibit an intense green-light emission at 515 nm. Moreover, the maximum luminance of the EL device on glass can reach 24721.8 cd m−2 at 10.0 V, and its maximum current efficiency is as high as 14.7 cd A−1 at 131.6 mA cm−2. It is noted that the flexible EL device on the PET substrate maintains a stable emission and nice working performance even if the bending angles arrive at 140°. Therefore, it suggests that TPE-An should have a promising future in EL device applications.

CAS / MDL: 7789-24-4
研究领域: 材料科学 · 光学 · 电子工程
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