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PROCESS BIOCHEMISTRY · 2021 · IF 3.757

Removal of phenylalanine from egg white powder: Two-step enzymatic method combined with activated carbon adsorption

Yujie Su,Yuzhen Wang,Cheng Lu,Luping Gu,Cuihua Chang,Junhua Li,David Julian McClements,Yanjun Yang

Individuals suffering from phenylketonuria require foods containing low levels of phenylalanine (Phe). In this research, we therefore developed a two-step enzymatic hydrolysis method followed by activated carbon treatment to remove Phe from egg white powder (EWP). Nine proteases were tested for their ability to expose or release Phe residues from the egg proteins, while nine kinds of activated carbon were tested as an adsorptive medium for removing Phe residues. Our results showed that trypsin combined with flavourzyme released the most Phe residues, and No.4 activated carbon was most effective at removing Phe residues. The percentage of Phe removal varied from 91.71–97.78% and the final mass yield from 230.08–342.45 g low Phe peptide (LPP) / Kg of EWP. The LPP mixtures obtained mainly containing amino acids and oligopeptides (< 600 Da). The EWP-LPP mixture obtained therefore has the potential to prepare medical foods for patients with phenylketonuria.

研究领域: 食品科学 · 医学
✓ 已验证 DOI 高影响因子
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ACS Omega · 2020 · IF 2.87

An Aminotransferase from Enhydrobacter aerosaccus to Obtain Optically Pure β-Phenylalanine

Xinming Feng,Jing Guo,Rubing Zhang,Wei Liu,Yujin Cao,Mo Xian,Huizhou Liu

An aminotransferase ω-TAEn was identified from Enhydrobacter aerosaccus. The ω-TAEn was successfully expressed in Escherichia coli and the obtained enzyme showed activity toward β-phenylalanine (β-phe) at optimal conditions. For optically pure (R)-β-phe, 50% yield was observed by kinetic resolution of racemic amino with pyruvate as the amino acceptor. To obtain (S)-β-phe, the lipase/ω-TAEn catalytic system was adopted. The ω-TAEn showed strict stereoselectivity to the amino donor. The formation of (S)-β-phe was observed using 3-aminobutyric acid as the amino donor, and (S)-β-phe was obtained by asymmetric synthesis with a yield of 82%.

研究领域: 生物化学 · 生物催化 · 酶学 · 化学生物学
✓ 已验证 DOI PubMed 高影响因子
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RSC Advances · 2022 ·Vol. 12 ·期 19 ·11967-11973 · IF 4.036

Chiral fluorescent sensor based on H8-BINOL for the high enantioselective recognition of D- and L-phenylalanine

Yafeng Zhang,Huizhen Wang,Hu Yu,Xiaoxia Sun

Phenylalanine an essential aromatic amino acid for humans and animals, cannot be synthesized by humans and animals on their own. However, it synthesizes important neurotransmitters and hormones in the body and is involved in gluconeogenesis and lipid metabolism. Moreover, the two opposite configurations of phenylalanine have different activities. For example, L-phenylalanine is a biologically active optical isomer involved in crucial biological processes, the lack of which will lead to intellectual disability, while D-phenylalanine only acts as a chiral intermediate. In this research, an H8-BINOL chiral fluorescent sensor modified with 1,2,3-triazole was synthesized in high yield (95%) by nucleophilic substitution and click reaction. The chiral fluorescent sensor showed high enantioselectivity toward phenylalanine. L-Phenylalanine enhanced the fluorescence response of the probe significantly, while D-phenylalanine had no obvious fluorescence response change. The enantioselective fluorescence enhancement ratio [ef = (IL − I0)/(ID − I0), where I0 is the fluorescence of the sensor without amino acids] for the highest fluorescence intensity at 20.0 equivalents of amino acids was 104.48. In this way, the probe could be used to identify and differentiate different configurations of phenylalanine.

研究领域: 生物化学 · 分析化学
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Science Advances · 2023 ·Vol. 9 ·期 22 · IF 13.6

Molecular architecture regulation for the design of instant and robust underwater adhesives

Jing Yu,Ruilin Xie,Mengyuan Zhang,Kaixiang Shen,Yuxuan Yang,Xiaodan Zhao,Xin Zhang,Yanfeng Zhang,Yilong Cheng

Development of underwater adhesives with instant and robust adhesion to diverse substrates remains challenging. A strategy taking the structural advantage of phenylalanine derivative, N-acryloyl phenylalanine (APA), is proposed to facilely prepare a series of underwater polymeric glue-type adhesives (UPGAs) through one-pot radical polymerization with commonly used hydrophilic vinyl monomers. The adjacent phenyl and carboxyl groups in APA realize the synergy between interfacial interactions and cohesion strength, by which the UPGAs could achieve instant (~5 seconds) and robust wet tissue adhesion strength (173 kilopascal). The polymers with varied hydrophobicity and substitutional groups as well as carboxyl and phenyl groups in separated components are designed to investigate the underwater adhesion mechanism. The universality of APA for the construction of UPGAs is also verified by the copolymerization with different hydrophilic monomers, and the applications of the UPGAs have been validated in diverse hemorrhage models and distinct substrates. Our work may give a promising solution to design potent underwater adhesives.

研究领域: 材料科学 · 生物医学工程 · 高分子化学
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BIOSENSORS & BIOELECTRONICS · 2023 · IF 12.6

Construction of an ultrasensitive dual-mode chiral molecules sensing platform based on molecularly imprinted polymer modified bipolar electrode

Xinli Wang,Jiahe Chen,Hui Xu,Yufei Fan,Xue Wang,Meng Zhang,Yue Liu,Binxiao Li,Jing Liu,Hong Zhou

Chiral molecules are abundant in nature. Phenylketonuria (PKU) is caused by the abnormal transformation of chiral molecules L-phenylalanine (L-Phe) in the human blood , which can cause irreversible harm to the human body. In this work, we documented an electrochemiluminescent (ECL) dual-mode sensor platform based on molecularly imprinted polymer (MIP) modified closed bipolar electrodes for high sensitivity detection of L-Phe and D-phenylalanine (D-Phe). In the anode chamber of a bipolar electrode modified with phenylalanine imprinting, Ru (bpy) 3 2+ underwent a redox reaction to produce a chemiluminescence response under the stimulation of a driving voltage . At the same time, the reduction of the cathode film of the bipolar electrode was promoted, and the color changed from dark blue to nearly white. Thus, the dual-mode detection of target molecules is realized. The detection range of the sensor for phenylalanine reached 0.01–10,000 nM, and the detection limits of L-Phe and D-Phe were 3.9 pM and 4.6 pM (S/N = 3), respectively. This dual-mode system achieved high stability and high specificity, and also successfully realized the detection of actual samples, which is expected to achieve future clinical applications.

CAS / MDL: 10025-77-1 102-69-2
研究领域: 分析化学 · 生物医学工程 · 传感器技术
✓ 已验证 产品关联 DOI PubMed 高影响因子
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BIOSENSORS & BIOELECTRONICS · 2025 · IF 10.5

Rapid indirect detection of N-lactoyl-phenylalanine using dual DNA biosensors based on solution-gated graphene field-effect transistor

Jiacheng Li,Ming Zhang,Cailing Zhang,Yin Zhang,Wenbin Chen,Hao Qu,Jian Liu,Lu Wang

As obesity rates continue to rise, there is an increasing focus on reducing obesity through exercise. People are becoming more aware of the importance of weight loss through physical activity. However, the effectiveness of exercise can vary significantly among individuals, making it challenging to evaluate its impact. Therefore, establishing a reliable method for assessing exercise effectiveness is crucial for enhancing exercise quality and reducing obesity risk. It is noteworthy that the relationship between N-lactoyl-phenylalanine (N-Lac-Phe) and energy metabolism has garnered considerable attention. In this study, we developed a N-Lac-Phe biosensor by detecting L-lactic acid (L-Lac) and L-phenylalanine (L-Phe) based on Solution-Gated Graphene Field-Effect Transistors (SGGT). Our findings showed that the L-Lac and L-Phe biosensors exhibited excellent linearity within concentration ranges of 300 pM to 300 nM for L-Lac and 3 nM–1000 nM for L-Phe, with R 2 values of 0.9934 and 0.9897, respectively. The detection accuracies for these two types of SGGT biosensors were 91.63 ± 6.97% and 99.39 ± 8.53%, respectively. Using the established N-Lac-Phe, L-Lac, and L-Phe relationship model (NLL model), we could calculate the concentration of N-Lac-Phe in the RAW264.7 culture medium based on the concentrations of L-Lac and L-Phe. The biosensors demonstrated excellent accuracy and selectivity, indicating their potential for rapidly evaluating the effectiveness of exercise.

研究领域: 生物传感器技术 · 医学检测 · 材料科学 · 代谢研究
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2016 · IF 0.566

Rapid Determination of Phenylalanine by Micro-chip Based Field Asymmetric Waveform Ion Mobility Spectrometry Technology

Da-Peng GUO,Yong-Huan WANG,Tian-Bai XU,Yuan ZHANG,Ling-Feng Li,Jin-Kai CHEN,Xiao-Zhi WANG,Peng LI,Ji-Kui LUO

The microchip field asymmetric ion mobility spectrometry (FAIMS) technology was used for rapid analysis of phenylalanine (PHE) using the metal diffusion tube-microchip μ-FAIMS system. The test pressure was set at 0.25 MPa, and the temperature of the gas generator for the diffusion tube was at 190 °C. The ion characteristic spectra were acquired under the optimized conditions with a gas flow rate of 2000 mL min −1 , a dispersion voltage of 152.8 V and a compensation voltage of −0.62 V for phenylalanine in positive mode. Phenylalanine gas samples with different concentrations were analyzed in detail by FAIMS. The results showed that the ion intensity was linearly correlated with phenylalanine concentration in the range from 6 mg L −1 to 20 mg L −1 , with the detection limit of 5.93 mg L −1 for phenylalanine. This investigation shows the feasibility of FAIMS technique for rapid detection of phenylalanine. The FAIMS instrument is simple, and has high sensitivity and fast response, and shows great potential for rapid detection of phenylalanine.

CAS / MDL: 63-91-2
研究领域: 分析化学 · 医学检验
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Materials Science & Engineering C-Materials for Biological Applications · 2020 · IF 5.88

Biomimetic synthesis of calcium carbonate under phenylalanine: Control of polymorph and morphology

Tingyu Yang,Jilagamazhi Fu,Liang Ma,Hong Du,Xiaoqing Yue,Bosheng Zhao,Cuiyan Wang

In biomineralization, organisms have the abilities to produce biominerals with superior properties. One of the most attractive features of biominerals is the presence of the proteins consisting of different contents of amino acids in crystals. In the present work, L-phenylalanine (Phe) was used as an additive for the controllable crystallization of calcium carbonate (CaCO 3 ). The obtained CaCO 3 crystals were characterized by field emission scanning electron microscopy (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), elemental analysis and high-resolution transmission electron microscopy (HRTEM). The experimental results suggest that single calcite crystals are formed at low Phe concentrations. High concentrations of Phe inhibit the nucleation and growth of calcite, and promote the formation of vaterite crystals with solid or hollow structures. The morphology and crystal form of CaCO 3 are also significantly affected by the flow rate of CO 2 . After that, a possible mechanism (competition mechanism) action of Phe in the formation of CaCO 3 is proposed. Finally, the effects of temperature on the formation of vaterite were determined to explore the growth mechanism of hexagonal vaterite. The work of controlling the preparation of CaCO 3 crystals in the presence of Phe will help us to imitate and learn nature, and bring new insights into understanding bionics. Meanwhile, it provides a new method for the synthesis of CaCO 3 biomaterials with different crystal forms and morphologies.

研究领域: 材料科学 · 生物矿化
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BMC PLANT BIOLOGY · 2023 ·Vol. 23 ·期 1 ·1-14 · IF 5.3

Functional and kinetics of two efficient phenylalanine ammonia lyase from Pyrus bretschneideri

Li Guohui,Song Cheng,Manzoor Muhammad Aamir,Li Daoyuan,Cao Yunpeng,Cai Yongping

Background The enzyme phenylalanine ammonia lyase (PAL) controls the transition from primary to secondary metabolism by converting L-phenylalanine (L-Phe) to cinnamic acid. However, the function of PAL in pear plants ( Pyrus bretschneideri ) has not yet been fully elucidated. Results We identified three PAL genes ( PbPAL1 , PbPAL2 and PbPAL3 ) from the pear genome by exploring pear genome databases. The evolutionary tree revealed that three PbPAL s were classified into one group. We expressed PbPAL1 and PbPAL2 recombinant proteins, and the purified PbPAL1 and PbPAL2 proteins showed strict substrate specificity for L-Phe, no activity toward L-Tyr in vitro, and modest changes in kinetics and enzyme characteristics. Furthermore, overexpression of PbAL1 and PbPAL1 -RNAi, respectively, and resulted in significant changes in stone cell and lignin contents in pear fruits. The results of yeast one-hybrid (Y1H) assays that PbWLIM1 could bind to the conserved PAL box in the PbPAL promoter and regulate the transcription level of PbPAL2. Conclusions Our findings not only showed PbPAL’s potential role in lignin biosynthesis but also laid the foundation for future studies on the regulation of lignin synthesis and stone cell development in pear fruit utilizing molecular biology approaches.

研究领域: 植物学 · 分子生物学
✓ 已验证 DOI 高影响因子
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SCIENCE OF THE TOTAL ENVIRONMENT · 2024 · IF 8.2

Computational-aided analysis of the pathway and mechanism of dichloroacetonitrile formation from phenylalanine upon chloramination

Rui Yu,Yunkun Qian,Yanan Chen,Yijun Shi,Jun Guo,Dong An

Dichloroacetonitrile (DCAN) is an emerging disinfection by-product (DBP) that is widespread in drinking water. However, the pathway for DCAN formation from aromatic amino acids remains unclear, leading to a lack of an understanding of its explicit fate during chloramination. In this study, we investigated the specific formation mechanism of DCAN during the chloramination of phenylalanine based on reaction kinetics and chemical thermodynamics. The reason for differences between aldehyde and decarboxylation pathways was explained, and kinetic parameters of the pathways were obtained through quantum chemistry calculations. The results showed that the reaction rate constant of the rate-limiting step of the aldehyde pathway with 1.9 × 10 −11  s −1 was significantly higher than that of decarboxylation (3.6 × 10 −16  s −1  M −1 ), suggesting that the aldehyde pathway is the main reaction pathway for DCAN formation during the chloramination of phenylalanine to produce DCAN. Subsequently, theoretical calculations were performed to elucidate the effect of pH on the formation mechanism, which aligned well with the experimental results. Dehydrohalogenation was found to be the rate-limiting step under acidic conditions with reaction rate constants higher than those of the rate-limiting step (expulsion of amines) under neutral conditions, increasing the rate of DCAN formation. This study highlights the differences in DCAN formation between the decarboxylation and aldehyde pathways during the chloramination of precursors at both molecular and kinetic levels, contributing to a comprehensive understanding of the reaction mechanisms by which aromatic free amino acids generate DCAN.

CAS / MDL: 1634-04-4
研究领域: 环境科学 · 化学
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ANALYTICAL CHEMISTRY · 2018 · IF 6.042

Chiral Sensing Platform Based on the Self-Assemblies of Diphenylalanine and Oxalic Acid

Lili Guo,Baozhu Yang,Datong Wu,Yongxin Tao,Yong Kong

Molecular self-assemblies offer a promising strategy for the synthesis of advanced materials for the construction of novel chiral sensing systems, and latest innovations on such self-assemblies are focused on simple building blocks in biology such as nucleic acids, lipids, and peptides. Herein, the self-assemblies of diphenylalanine (FF) and oxalic acid (OA) were prepared as the chiral sensing device for the recognition of tryptophan (Trp) isomers. Interestingly, the self-assemblies composed of OA and FF with different charging states (neutral, positively charged, and negatively charged) exhibited quite different morphologies, resulting in significantly different chiral recognition ability toward the Trp isomers. Also, in this work, the temperature sensitivity and chiral selectivity of the proposed FF-OA self-assemblies were also studied. From a practical point of view, the FF-OA self-assemblies were finally applied for the determination of precise levels of d-Trp in the racemic mixture of Trp isomers.

研究领域: 生物化学 · 材料科学 · 分析化学
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ACS Nano · 2022 · IF 18.027

Chirality-Dependent Copper–Diphenylalanine Assemblies with Tough Layered Structure and Enhanced Catalytic Performance

Gong Zhang,Yaoyu Liang,Yuefei Wang,Qing Li,Wei Qi,Wei Zhang,Rongxin Su,Zhimin He

Chiral regulation to prepare functional materials has aroused considerable interest in recent years. However, little is known on the effect of chirality of ligands in the metal–organic coordination assembly process. We report the self-assembly of diphenylalanine peptide (Phe-Phe, FF), the core fragment of Aβ protein, with metal copper ion (Cu2+) into metal–organic assemblies with chirality-encoded structures and properties. The chirality-dependent metal–dipeptide assembles with different morphologies and supramolecular chirality were obtained by facile changing of the FF chirality. Single-crystal results indicate that (L)-FF coordinated with Cu2+ into a cross-chain structure with a five-coordinated style, while the racemates of (L+D)-FF with Cu2+ crystallized into an (L)-Cu2+-(D)-Cu2+ alternated four-coordinating structure, enabling a higher mechanical and catalytic performance. The Young’s modulus of (L+D)-FF-Cu is as high as 34.36 GPa, which is 2.45 times higher than that of (L)-FF-Cu. Furthermore, both of them follow the characteristic enzyme kinetics and show higher catalytic activity than natural laccase at the same mass concentration. Specifically, the calculated catalytic efficiency (kcat/KM) of (L+D)-FF-Cu is 1.14 times higher than that of (L)-FF-Cu, and the (L+D)-FF-Cu shows significantly enhanced stability and reusability compared with (L)-FF-Cu. The results reveal that highly functional materials could be constructed by encoding the chirality of molecular building blocks.

研究领域: 材料科学 · 生物化学 · 纳米技术
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