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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2022 ·Vol. 103 ·期 4 ·2014-2022 · IF 4.125

Effect of co-treatment of microwave and exogenous l-phenylalanine on the enrichment of flavonoids in Tartary buckwheat sprouts

Wenping Peng,Nan Wang,Shunmin Wang,Junzhen Wang,Zixiu Bian

BACKGROUND Tartary buckwheat is rich in flavonoids. The application of physical processing technology and exogenous materials treatment can effectively promote grain germination and the accumulation of bioactive secondary metabolites. The content of four flavonoids, the activities of key enzymes (phenylalanine ammonia-lyase (PAL), chalcone isomerase (CHI), flavonol synthase (FLS)) and the expression of key enzyme genes ( FtPAL , FtCHI , FtFLS1 , FtFLS2 ) in Tartary buckwheat sprouts treated with microwave and l -phenylalanine ( l -Phe) were investigated, and the relationship between them was analyzed to explore the mechanism of promoting flavonoid accumulation, and to provide a theoretical basis for the development of functional Tartary buckwheat sprout food. RESULTS Germination can promote the synthesis of flavonoids. The contents of chlorogenic acid and rutin in 7-day sprouts increased by 13 420.63% and 225.12% compared with seeds, respectively. Under the best treatment condition T 3 (microwave 250 W, 90 s, 2.9 mmol L −1 L-Phe), the specific activities of PAL, CHI and FLS in 5-day-old sprouts increased by 47.84%, 53.04% and 28.02% compared with control check (CK), respectively; and the expression of FtPAL , FtCHI and FtFlS1 increased by 39.84%, 24.78% and 33.72% compared with CK, respectively. Correlation analysis showed that the content of flavonoids in Tartary buckwheat sprouts was significantly positively correlated with the specific activities of key enzymes ( P < 0.01) and dynamically correlated with genes related to the synthesis of three enzymes. CONCLUSION It suggested that microwave and l -Phe treatment may promote the synthesis of flavonoids by promoting the expression of key enzymes genes in phenylpropane metabolism and controlling the activity of key enzymes in phenylpropane metabolism. © 2022 Society of Chemical Industry.

CAS / MDL: 63-91-2
研究领域: 食品科学 · 植物生理学 · 生物化学
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2016 ·Vol. 51 ·期 9 ·1988-1996 · IF 1.504

The role of pulsed electric fields treatment in enhancing the stability of amino acid – sugar complexes:- interactions between L-Phenylalanine and β-Cyclodextrin

Zhi-Hong Zhang,Lang-Hong Wang,Xin-An Zeng,Charles S. Brennan,Margaret Brennan,Zhong Han

Summary In this work, the effect of pulsed electric fields (PEF) treatment on the interactions between amino acids (using L-Phenylalanine: L-Phe) and sugar (using β-Cyclodextrin: β-CD) complex was analysed by fluorescence spectroscopy, Raman spectroscopy and simultaneous thermal analyzer. Moreover, the molecular dynamics of β-CD–L-Phe inclusion complex treated by PEF was calculated by molecular modelling. The results indicated that β-CD–L-Phe complexes are formed by a molar ratio of 1:1, and the stability constant of such complexes increased from 147 to 614 M −1 by PEF treatment. Thermal characterisations of β-CD–L-Phe complexes indicated that the PEF treatment could increase the yield of complexes. The PEF treatment resulted in an increase in the reaction enthalpy of β-CD–L-Phe inclusion complexes by DSC curve. These results show that PEF treatment has the potential to promote the chemical processing, especially the small organic molecules participate in inclusion or cross-linking reaction.

CAS / MDL: 63-91-2
研究领域: 生物化学 · 食品科学 · 分子生物学
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JOURNAL OF FLUORESCENCE · 2022 ·Vol. 32 ·期 3 ·983-992 · IF 2.525

Chiral Fluorescence Recognition by Anthracene Fluorescent Dyes ⊂ Water-Soluble Pillar[5] arene containing Phosphonic Acid Group (PWP[5])

Chen Yuliang,Lai Kaijie,Cai Jinmi,Li Yicheng,Wang Haibo

Chirality plays a pivotal role in drugs, agrochemicals and food additives et al. The enantiomers of a chiral molecule often show huge difference in bioactivity, metabolism, and toxicity et al. thereby, the recognition of chiral molecules shows an increasingly important priority. In this paper, a novel method for chiral fluorescence recognition based on anthracene fluorescent dyes (AD) ⊂ water-soluble pillar[5] arene containing phosphonic acid group (PWP[5]) is developed. The AD as guest molecule can complex with PWP [5] to form 1:1 AD ⊂ PWP[5] assembly, and this assembly can be further used as a fluorescent probe to identify D/L-phenylalanine and D/L-phenylalaninol by fluorescent titration. The fluorescence intensity of the assembly was significantly reduced for D-phenylalanine and D-phenylalaninol, while L-phenylalanine or L-phenylalaninol was added to AD ⊂ PWP[5] assembly, the fluorescence intensity of the assembly almost unchanged. Hence, the chiral recognition based on assembly between the achiral fused ring fluorescent dye and achiral PWP[5] was developed.

CAS / MDL: 5267-64-1 63-91-2
研究领域: 化学 · 生物化学 · 药物化学
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LANGMUIR · 2018 · IF 3.789

Construction of a Liquid Crystal-Based Sensing Platform for Sensitive and Selective Detection of l-Phenylalanine Based on Alkaline Phosphatase

Lele Zhou,Qiongzheng Hu,Qi Kang,Ming Fang,Li Yu

The detection of l-phenylalanine (l-Phe) has become one of the most pressing issues concerning diagnosis and treatment of phenylketonuria in neonates; however, a simple and robust methodology is yet to be developed. Here, the application of novel liquid crystals (LCs)-sensing platform for sensitive, selective, and label-free detection of l-Phe was reported at the first time. We devised a strategy to fabricate the sodium monododecyl phosphate (SMP)-decorated LC sensing platform with the appearance of dark. Then, a dark to bright (D–B) optical images alteration of LCs was observed after transferring alkaline phosphatase (ALP) to the interface, owing to cleavage of SMP induced by ALP. LCs remained dark images after the SMP-decorated interface in contact with the pre-incubated ALP and l-Phe. Such optical appearance resulted from the inhibition of ALP by l-Phe, which was further verified by the isothermal titration calorimetry (ITC). The strategy was applied to sensing l-Phe, which have been proven to allow for sensitively and selectively differentiation of l-Phe from interfering compounds with similar aromatic groups, as well as seven other essential amino acids. More importantly, the detection limit of l-Phe reached 1 pg/mL in urine samples, further demonstrating its value in the practical applications. Results obtained in this study clearly demonstrated the superiority of LCs toward the l-Phe detection, which can pave a way for the development of high performance and robust probes for l-Phe detection in clinical applications.

CAS / MDL: 123-31-9 50-81-7
研究领域: 生物化学 · 医学诊断 · 材料科学
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International Journal of Electrochemical Science · 2023 · IF 1.5

Simultaneous Determination of Theophylline and Caffeine Using Poly(L-phenylalanine)-Reduced Graphene Oxide Modified Glassy Carbon Electrode

Lin Zhang,Ting Wang,Xinxia Fan,Dongmei Deng,Yuanyuan Li,Xiaoxia Yan,Liqiang Luo

Theophylline (TP) and caffeine (CF) are two purine alkaloids which widely exist in our human diet. In the present work, poly(L-phenylalanine)-reduced graphene oxide (P(L-Pal)/rGO) modified glassy carbon electrode (GCE) was fabricated and applied to simultaneously determine the concentrations of TP and CF. The P(L-Pal)/rGO composite film was prepared by one-step electropolymerization using cyclic voltammetry, and the surface morphology was investigated by scanning electron microscope. The electrochemical behaviors of TP and CF on P(L-Pal)/rGO/GCE were investigated using cyclic voltammetry and differential pulse voltammetry. By optimizing parameters, the fabricated sensor exhibited excellent performance to simultaneously determine TP and CF in a wide linear range of 1−260 μM. The detection limits were 0.35 and 0.5 μM (S/N = 3), respectively. The presented method shows good sensitivity and stability, and can be used for the determination of TP and CF in samples of green tea, coffee and tablets.

研究领域: 分析化学 · 电化学
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JOURNAL OF SEPARATION SCIENCE · 2015 ·Vol. 38 ·期 18 ·3279-3287 · IF 2.737

Preparation of “dummy” l-phenylalanine molecularly imprinted microspheres by using ionic liquid as a template and functional monomer

Ji Li,Xiaoling Hu,Ping Guan,Dongmen Song,Liwei Qian,Chunbao Du,Renyuan Song,Chaoli Wang

In this study, dummy imprinting technology was employed for the preparation of l- phenylalanine-imprinted microspheres. Ionic liquids were utilized as both a “dummy” template and functional monomer, and 4-vinylpyridine and ethylene glycol dimethacrylate were used as the assistant monomer and cross-linker, respectively, for preparing a surface-imprinted polymer on poly(divinylbenzene) microspheres. By the results obtained by theoretical investigation, the interaction between the template and monomer complex was improved as compared with that between the template and the traditional l- phenylalanine-imprinted polymer. The batch experiments indicated that the imprinting factor reached 2.5. Scatchard analysis demonstrated that the obtained “dummy” molecularly imprinted microspheres exhibited an affinity of 77.4 M·10 −4 , significantly higher that of a traditional polymer directly prepared by l- phenylalanine, which is in agreement with theoretical results. Competitive adsorption experiments also showed that the molecularly imprinted polymer with the dummy template effectively isolated l- phenylalanine from l- histidine and l- tryptophan with separation factors of 5.68 and 2.68, respectively. All these results demonstrated that the polymerizable ionic liquid as the dummy template could enhance the affinity and selectivity of molecularly imprinted polymer, thereby promoting the development of imprinting technology for biomolecules.

研究领域: 化学 · 生物化学
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Analytical Methods · 2024 ·Vol. 16 ·期 24 ·3907-3916 · IF 2.7

Modifying carbon dots with L-phenylalanine for rapid discrimination of tryptophan enantiomers

Bozhi Lang,Wenming Ma,Xuan Liao,Yaning Duan,Cuiling Ren,Hongli Chen

New chiral carbon dots (CDs), L-PCDs, for discriminating tryptophan (Trp) enantiomers were prepared in this work. Firstly, original CDs were synthesized through a hydrothermal method using pyridine-2,6-dicarboxylic acid and o-phenylenediamine as raw materials. Then, the surface of original CDs was modified with L-phenylalanine to create chiral fluorescent carbon L-PCDs. In the presence of D-Trp, the fluorescence intensity of L-PCDs decreased significantly while it remained unchanged in the presence of L-Trp. The chiral sensing system used in this study has a rapid response time of 3 minutes and can identify enantiomers with an enantioselectivity (ID/IL) of up to 3.3. For D-Trp, a good linear relationship can be obtained in the range of 0.3–4.2 mM with a limit of detection of 0.06 mM. This sensor allows for both quantitative detection of D-Trp and determination of enantiomeric percentage in the racemate. The chiral recognition mechanism is attributed to the different interaction between D-/L-Trp and L-PCDs.

研究领域: 分析化学 · 生物化学
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ACS Omega · 2018 · IF 0

Hierarchical Assembly of l-Phenylalanine-Terminated Bolaamphiphile with Porphyrin Show Tunable Nanostructures and Photocatalytic Properties

Cuiyun Zhou,Xuenan Feng,Rong Wang,Gengxiang Yang,Tianyu Wang,Jianzhuang Jiang

Demands related to clean energy and environmental protection promote the development of novel supramolecular assemblies for photocatalysis. Because of the distinctive aggregation behaviors, bolaamphiphiles with two hydrophilic end groups could be theoretically the right candidates for the fabrication of high-performance photocatalysis. However, photocatalytic applications based on bolaamphiphilic assemblies were still rarely investigated. Especially, the relationship between diverse assembled nanostructures and the properties for different applications is urgently needed to be studied. Herein, we demonstrate that using the hierarchical assembly of bolaamphiphiles could correctly induce the porphyrin supramolecular architectures with much better photocatalytic performances than the aggregations containing 450 times of the porphyrin molecules, even though both molecular structures as well as the J-aggregations of porphyrin building blocks are same in two different systems. Thus, the co-assembly of l-phenylalanine terminated bolaamphiphile (Bola-F) and the porphyrin containing four hydroxyl groups (tetrakis-5,10,15,20-(4-hydroxyphenyl)porphyrin) can form microtube in methanol and forms fibers/spheres in methanol/water mixture. For catalyzing the photodegradation of rhodamine B, the small amount of J-aggregated porphyrin within Bola-F microtubes show much better photocatalytic performance comparing with that of huge porphyrin J-aggregations in fibers/spheres. The supramolecular assemblies as well as the photocatalysis were thoroughly characterized by different spectroscopies and electron microscopy. It is demonstrated that the co-assembly with bolaamphiphiles could inhibit the energy transfer of porphyrin aggregation and subsequently benefit the electron transfer and corresponding photocatalysis under photo-irradiation. This work is not only useful for further understanding the hierarchically supramolecular assembly but also provides a new strategy for making novel functional supramolecular architectures based on the assembly of bolaamphiphiles and porphyrins.

CAS / MDL: 81-88-9
研究领域: 材料科学 · 化学 · 环境科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2024 · IF 4.3

Synthesis of chiral hollow polymer microspheres and their applications in the spectroscopic chiral discrimination of tryptophan isomers

Nan Shi,Baozhu Yang,Junyao Li,Wenrong Cai,Laidi Xu,Yongxin Tao,Yong Kong

Hollow polymer microspheres (HPMs) were synthesized, which were then hydrolyzed in aqueous ammonia to produce carboxyl (–COOH) groups on their surface. L-phenylalanine (L-Phe) was grafted to the hydrolyzed HPMs (H-HPMs) through amidation reactions, endowing the H-HPMs with chirality. The resultant chiral HPMs (C-HPMs) were used for the chiral discrimination of tryptophan (Trp) isomers. Due to the same rotatory   direction of L-Phe and L-Trp, the C-HPMs showed greatly higher selectivity toward L-Trp than its isomer. After being adsorbed by the C-HPMs, the absorbance of the residual L-Trp is significantly lower than that of the residual D-Trp, and thus spectroscopic chiral discrimination of the Trp isomers was successfully achieved. The Trp isomers were also discriminated by the chiral solid polymer microspheres (C-SPMs), while the difference in the absorbance of the residual L-Trp and D-Trp is remarkably smaller than that obtained by the C-HPMs. The outstanding discrimination capability of the C-HPMs might be ascribed to their high surface permeability resulted from their unique hollow structure.

研究领域: 材料科学 · 生物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2018 · IF 3.412

Mimicking a New 2-Phenylethanol Production Pathway from Proteus mirabilis JN458 in Escherichia coli

Jinbin Liu,Jing Jiang,Yajun Bai,Tai-ping Fan,Ye Zhao,Xiaohui Zheng,Yujie Cai

Bacteria rarely produce natural 2-phenylethanol. We verified a new pathway from Proteus mirabilis JN458 to produce 2-phenylethanol using Escherichia coli to coexpress l-amino acid deaminase, α-keto acid decarboxylase, and alcohol dehydrogenase from P. mirabilis. Based on this pathway, a glucose dehydrogenase coenzyme regeneration system was constructed. The optimal conditions of biotransformation by the recombinant strain E-pAEAKaG were at 40 °C and pH 7.0. Finally, the recombinant strain E-pAEAKaG produced 3.21 ± 0.10 g/L 2-phenylethanol in M9 medium containing 10 g/L l-phenylalanine after a 16 h transformation. Furthermore, when the concentration of l-phenylalanine was 4 g/L (24 mM), the production of 2-phenylethanol reached 2.88 ± 0.18 g/L and displayed a higher conversion rate of 97.38 mol %.

研究领域: 微生物学 · 生物化学 · 代谢工程
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ChemElectroChem · 2022 ·Vol. 9 ·期 12 ·e202200082 · IF 4.782

Proton Acid Doped Superior Capacitive Performances of Pseudocapacitance Electrodes for Energy Storage

Jian Liu,Xiaohang Ma,Zhenfa Zi

Graphical Flower power : Polyaniline nano-flowers doped with L-phenylalanine (PANI-NF) porous structures were prepared. The supercapacitor assembled with PANI-NF symmetrical electrode showed maximum specific capacitance of 580 F g −1 (I=0.5 A g −1 ), a maximum energy density of 53.9 Wh kg −1 , and excellent cycle stability at high current density. It made an LED work continuously for more than 600 seconds after charging for 10 seconds. In this work, three-dimensional (3D) nanostructures of polyaniline nano-sheets, nano-particles, nano-nets and nano-flowers were synthesized with valine, sulfuric acid, sodium acetate and L-phenylalanine as doping acids, respectively. Conductive polyaniline with 3D nanostructure was proven as an excellent energy storage material because of its superior electrical properties and unique structure. The porous structure not only greatly improved the charge transfer efficiency and reduced the resistance, but also improved the cycle stability and energy storage of the electrode material. Polyaniline nano-flowers doped with L-phenylalanine (PANI-NF) showed a maximum specific capacitance of 580 F g −1 (I=0.5 A g −1 ), a maximum energy density of 53.9 Wh kg −1 , and excellent cycle stability at high current density.

CAS / MDL: 62-53-3 63-91-2 72-18-4
研究领域: 材料科学 · 能源存储
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2011 · IF 1.77

Determination of l-phenylalanine on-line based on molecularly imprinted polymeric microspheres and flow injection chemiluminescence

Huamin Qiu,Yulei Xi,Fuguang Lu,Lulu Fan,Chuannan Luo

A novel molecular imprinting-chemiluminescence (MIP-CL) sensor for the determination of l -phenylalanine (Phe) using molecularly imprinted polymer (MIP) as recognition element is reported. The Phe-MIP was synthesized using acrylamide (AM) as functional monomer and ethylene glycol dimethacrylate (EGDMA) as cross-linker, 2,2-azobisisobutyronitrile (AIBN) as initiator and the polymers’ properties were characterized. Then the synthesized MIP was employed as recognition element by packing into flow cell to establish a novel flow injection CL sensor. The CL intensity responded linearly to the concentration of Phe in the range 1.3   ×   10 −6 to 5.44   ×   10 −4   mol/L with a detection limit of 6.23   ×   10 −7   mol/L (3 σ ), which is lower than that of conventional methods. The sensor is reusable and has a great improvement in sensitivity and selectivity for CL analysis. As a result, the new MIP-CL sensor had been successfully applied to the determination of Phe in samples.

CAS / MDL: 63-91-2
研究领域: 分析化学 · 生物医学
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