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FOOD CHEMISTRY · 2023 · IF 8.8

A novel integrated automatic strategy for amino acid composition analysis of seeds from 67 species

Yelin Ding,Qirui Bi,Dongdong Huang,Jingmei Liao,Lin Yang,Xiaoxiao Luo,Peilei Yang,Yun Li,Changliang Yao,Wenlong Wei,Jianqing Zhang,Jiayuan Li,Yong Huang,De-an Guo

The composition and quantity of amino acids (AAs) in seeds are complicated due to the various origins and modifications of different species. In this study, a novel automatic neutral loss filtering (ANLF) strategy based on accurate mass searching by Python was developed to analyze the free and hydrolyzed AA-phenyl isothiocyanate (PITC) derivatives from seeds of Gymnosperm and Angiosperm phyla. Compared with traditional strategies, ANLF showed much higher accuracy in screening AA derivatives by filtering nitrogen-containing non-AA compounds and efficiency in processing large datasets. Meanwhile, the content phenotype of 20 proteinogenic AAs from seeds of these two families was characterized by a 35-min HPLC method combined with an automated peak-matching strategy. AA profiles of 232 batches of seeds from 67 species, consisting of 19 proteinogenic AAs, 21 modified AAs, and 77 unknown AAs, would be a good reference for their application in food and medicine.

CAS / MDL: 64-18-6
研究领域: 生物化学 · 植物科学 · 分析化学 · 食品科学
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INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

Characterization and assessment of free amino acids in different varieties of sugarcane

Lu Wang,Limei Xiao,Shoujing Zheng,Jie Pang,Jiebo Chen

A better understanding of amino acids (AA) characteristics is beneficial for breeding, processing and storage of sugarcane. The differences and classification in AA of 10 different sugarcane varieties (S1-S10) were investigated in this study. Varieties affected components and concentrations of free AA ( p < 0.05) significantly. The total AA of sugarcanes ranged from 51.44 to 781.61 mg/L, while the content of essential amino acids (EAA) was in the range of 0.72–60.98 mg/L. Glu (glutamic acid) was the most abundant free amino acids in all varieties of sugarcane except S4. Even though S6 had the highest concentration of medicinal AA (781.61 mg/L), the highest proportion of medicinal AA in total AA was found in S5 (81.76%). S6 got the highest comprehensive score in amino acids based on the results of Principal Component Analysis (PCA). The cluster analysis roughly divided the sugarcanes into 2 groups. Group Ⅰ including S1, S6, S2 and S5 got positive scores in PCA might had great edible and medicinal development and utilization value.

研究领域: 食品科学 · 植物学
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Analytical Methods · 2017 ·Vol. 9 ·期 43 ·6131-6138 · IF 1.9

Separation and detection of free D- and L-amino acids in tea by off-line two-dimensional liquid chromatography

Xiangyu Wang,Huihui Wu,Rongying Luo,Donghai Xia,Zhengjin Jiang,Hai Han

D-amino acids are currently paid attention to as new physiologically active substances. Foodstuffs and beverages containing D-amino acids are a matter of interest. Until now, the profiles of D-amino acids have not been reported in natural and fermented teas except theanine. In this study, an off-line 2D-HPLC method combining a Gemini C18 column and a CHIRALPAK® IC-3 column or a self-prepared poly(MQD-co-HEMA-co-EDMA) monolithic capillary column was employed for the separation and detection of D-amino acids in tea samples with the co-existence of a large amount of L-amino acids. The free amino acid fractions in longjing, black, oolong, and pu-erh tea samples were separated and collected after pre-column derivatization using 9-fluorenylmethoxycarbonyl (FMOC) chloride in the reversed-phase mode, and then were concentrated and separated to D- and L-forms on a chiral column. Among them, the D-form of isoleucine (Ile) (1.0–1.6%), alanine (Ala) (0.1–0.8%), phenylalanine (Phe) (0.1–0.4%), valine (Val) (0.2–0.3%), serine (Ser) (0.1–0.2%), aspartic acid (Asp) (0.2%), and proline (Pro) (0.1%) were detected in longjing and oolong teas. Differences between natural tea and fermented tea in the profiles of D-amino acids as well as the total amino acids were also observed. The results provided useful information for the bio-function research of D-amino acids in tea.

研究领域: 食品科学 · 分析化学 · 生物化学
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CANADIAN JOURNAL OF CHEMICAL ENGINEERING · 2024 ·Vol. 102 ·期 10 ·3532-3549 · IF 1.6

Pore size regulation of ZIFs for adsorptive separation of branched chain and aromatic amino acids

Wen Jiang,Shifeng Miao,Yujie Yang,Yu Long

This research endeavour aims to investigate the adsorptive separation of the branched chain (BCAA) and aromatic amino acids (AAA). Based on the different molecular sizes of BCAA and AAA, zeolitic imidazolate frameworks (ZIFs) with different pore structures were prepared by regulating the size of imidazole ligands. The structure and pore shape were characterized by Fourier transform infrared spectroscopy (FT-IR), x-ray diffraction (XRD), scanning electron microscope (SEM), and BET surface area (BET). The results indicated the successful synthesis of ZIF-[Co(mIm) 2 ], ZIF-[Co(eIm) 2 ], and ZIF-[Co(pIm) 2 ] with pore size distribution of 7.821, 6.943, and 9.394 Å, and particle size of these ZIFs was approximately 4 μm. ZIF-[Co(eIm) 2 ] was chosen as the optimal ZIFs for the separation of BCAA and AAA. The adsorption experiment was evaluated in the respective single and binary systems. The corresponding data in a single system demonstrated that ZIF-[Co(eIm) 2 ] showed good adsorption performance for BCAA and poor for AAA. Furthermore, the adsorption behaviour under experimental conditions conformed well to the pseudo-second-order kinetic model and Langmuir isotherm. ZIF-[Co(eIm) 2 ] had great separation ability for BCAA/AAA in their binary system. Finally, regeneration studies further manifested that ZIF-[Co(eIm) 2 ] exhibited fine reusability performance with adsorption efficiencies still higher than 70% after five cycles. This study exhibits a novel path for the design of adsorbents for efficient separation of BCAA/AAA.

CAS / MDL: 6147-53-1
研究领域: 生物化学 · 材料科学 · 分离技术
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Heliyon · 2024 · IF 3.4

Targeted metabolomics of muscle amino acid profles and hepatic transcriptomics analyses in grass carp (Ctenopharyngodon idellus) fed with broad beans

Meilin Hao,Junhong Zhu,Yuxiao Xie,Wenjie Cheng,Lanlan Yi,Sumei Zhao

While tissue amino acid compositions reflect that of the dietary protein source, and the liver orchestrates amino acid metabolism. In this study, we investigated the muscle amino acid profiles in ordinary and crisp grass carp. The 22 amino acids were measured, and seventeen showed significant concentration differences. To understand the molecular mechanisms behind changes, we analyzed the liver transcriptome, and the 2519 differentially expressed genes (DEGs) were identified, with 1156 up-regulated and 1363 down-regulated genes. DEGs were enriched in ribosome-related biological processes. KEGG pathway analysis showed enrichment in tryptophan metabolism, lysine degradation, valine, leucine and isoleucine degradation, galactose metabolism, and glutathione metabolism with up-regulated genes, arginine and proline metabolism, arginine biosynthesis and alanine, aspartate, amino sugar and nucleotide sugar metabolism, N-Glycan biosynthesis and glutamate metabolism with down-regulated genes. A protein-protein interaction network with 260 nodes and 249 edges was constructed, and 3 modules were extracted. The top 10 hub genes with close connections to other nodes were ITM1, STT3B, SEL1L, UGGT1, MLEC, IL1B, ALG5, KRTCAP2, NFKB2, and IRAK3. In summary, this study identified candidate genes and focused on amino acid and glycan metabolism pathways, providing a reference for further investigation into liver amino acid metabolism in grass carp fed with broad beans.

CAS / MDL: 73-32-5
研究领域: 水产养殖学 · 分子生物学 · 营养学
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Bioanalysis · 2024 · IF 1.9

LC-MS/MS-based bioanalysis of branched-chain and aromatic amino acids in human serum

Tianyi Wang,Yalian Zhang,Luan Jia,Ying Li,Lu Wang,Yanru Zhu,Yuxin Jiang,Furong Zhao,Shuang Wang,Dan Song

Aim: Branched-chain amino acids (BCAAs) and aromatic amino acids (AAAs) were suggested as potential biomarkers in liver disease. This study aimed to develop and validate a simple and rapid LC-MS/MS method to simultaneously measure serum BCAAs and AAAs levels in patients with liver injury, and further establish reference intervals of Chinese healthy adult populations.Patients & methods: Samples were prepared by a one-step protein precipitation and analysis time was 4 min per run.Results: The validation results showed good linearity (r2 >0.9969), satisfactory accuracy (94.44% – 107.75%) and precision (0.10% – 5.90%).Conclusion: This method proved to be suitable for high-throughput routine clinical use and could be a valuable adjunct diagnosis tool for liver injury and other clinical applications.

CAS / MDL: 64-18-6
研究领域: 临床医学 · 生物分析
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PROTEIN EXPRESSION AND PURIFICATION · 2024 · IF 1.4

Biosynthesis of α-keto acids and resolution of chiral amino acids by l-amino acid deaminases from Proteus mirabilis

Junzhang Chang,Yuxin Zhang,Zhiwei Li,Yunfeng Ma,Xueqin Hu,Jingwen Yang,Hongbin Zhang

Chiral amino acids and their deamination products, α-keto acids, have important applications in food, medicine, and fine chemicals. In this study, two l -amino acid deaminase genes from Proteus mirabilis , PM473 of type Ⅰ and PM471 of type Ⅱ were cloned and expressed in Escherichia coli respectively, expected to achieve the chiral separation of amino acids . Extensive substrate preference testing showed that both deaminases had catalytic effects on the d -amino acid component of the D, l -amino acids, and PM473 has a wider catalytic range for amino acids. When D, L-Cys was used as the substrate, all L-Cys components and 75.1 % of D-Cys were converted to mercapto pyruvate , and the remaining D-Cys was a single chiral enantiomer . Molecular docking analysis showed that the interaction between the substrate and the key residues affected the stereoselectivity of enzymes . The compatibility of hydrophobicity between the binding pocket and substrate may be the basic factor that affects the substrate selectivity. This work provides an alternative method for the production of α-keto acids and the resolution of chiral amino acids.

研究领域: 生物化学 · 生物催化 · 酶学 · 药物化学
✓ 已验证 DOI PubMed 高影响因子
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BIOSENSORS & BIOELECTRONICS · 2019 · IF 9.518

D-amino acid electrochemical biosensor based on D-amino acid oxidase: Mechanism and high performance against enantiomer interference

Tingting Tian,Mingxia Liu,Lixia Chen,Fengjiao Zhang,Xin Yao,Hong Zhao,Xiangjun Li

For D-amino acid (DAA) electrochemical biosensors , it is necessary to achieve chiral recognition in racemic solutions or mixtures. However, common chiral recognition is only performed in a single isomer solution. Here, D-amino acid oxidase (DAAO) was used as a chiral selector, and carbon nanotubes (CNTs) as a signal amplifier to construct a non-mediator-style DAA biosensor. The biosensor showed high performance against enantiomer interference: in alanine (Ala) enantiomer mixtures, accurate quantification of D-Ala was achieved when the concentration ratio of L-Ala to D-Ala was 100. In Ala racemic solutions, the linear equation slope was almost consistent with that of standard D-Ala. This high performance was due to the combination of stereoselectivity (enzyme protein) and a catalytic reaction (redox center). The mechanism for the electrical signal change of the biosensor was explored and verified by cyclic voltammetry (CV). The results showed that (i) flavin adenine dinucleotide (FAD, redox center of DAAO) was a direct electroactive substance that produced a reduction peak current; in the presence of O 2 , the amount of FAD increased leading to an increase of the reduction peak current. (ii) In the presence of DAA, the chemical reaction FAD + DAA  →  imino acids +  FADH 2 occurred and consumed FAD, which resulted in its decrease; thus, the reduction peak current also decreased. Under the same oxygen concentration, the linear decrease of the reduction peak current in the presence of DAA was due to FAD consumption. The biosensor was used for practical analyses in milk and urine samples with satisfactory results.

研究领域: 生物化学 · 分析化学
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Current Pharmaceutical Analysis · 2018 ·Vol. 14 ·期 6 ·562-570 · IF 0.859

Amino Acids from Ganoderma lucidum: Extraction Optimization, Composition Analysis, Hypoglycemic and Antioxidant Activities

Zhang Hui,Jiang Huijie,Zhang Xiaojing,Yan Jizhong

Background: Ganoderma lucidum is a well-known edible mushroom and traditional Chinese medicine, but there were no comprehensive reports on the extraction, analysis and activities test of Ganoderma lucidum Amino Acids (GLAA). Objective: The present study was aimed to optimize the extraction process of GLAA and analyze the amino acid composition of GLAA, combined with preliminary activity evaluation. Methods: The hydrochloric acid-hydrolysis method for extraction of GLAA was optimized by Response Surface Methodology (RSM) with Box-Behnken Design (BBD). The amino acid composition of GLAA was analyzed by PITC pre-column derivation with HPLC method and amino acid automatic analyzer. The hypoglycemic and antioxidant activities of GLAA were assayed by inhibitory rate of α- glucosidase and DPPH radical scavenging rate, respectively. Results: The optimal extraction conditions were obtained: liquid-to-solid ratio 20:1 mL/g, extraction time 9.5 h, hydrochloric acid concentration 7.0 mol/L, and the yield of GLAA was 4.78 ± 0.21 %. The result of amino acid automatic analyzer showed that the content of total amino acids in GLAA was 2.94 %, including 18 kinds of amino acids, and the most abundant amino acid was leucine (0.37 %). The results of activity tests in vitro showed that GLAA exhibited high α-glucosidase inhibitory rate with IC50 value of 380.62 μg/mL and a certain scavenging DPPH activity with IC50 of 484.54 μg/mL. Conclusion: The RSM with BBD was successfully implemented for optimization of the extraction parameters of GLAA. The GLAA was rich in 18 kinds of amino acids and possessed strong hypoglycemic and antioxidant activities.

研究领域: 食品科学 · 中药学 · 生物化学
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Scientific Reports · 2017 ·Vol. 7 ·期 1 ·1-9 · IF 4.259

PH-Dependent Enantioselectivity of D-amino Acid Oxidase in Aqueous Solution

Liu Qingju,Chen Li,Zhang Zhikun,Du Bibai,Xiao Yating,Yang Kunhao,Gong Lingling,Wu Li,Li Xiangjun,He Yujian

D-amino acid oxidases (DAAO) are stereospecific enzymes which are generally almost inactive towards L-enantiomer in neutral solution when L-, D-amino acids are supplied as substrates. In this paper, the D-amino acid oxidase can catalytic oxidize L-amino acids by modulating pH of aqueous solution. With L-Pro as substrate, the catalytic rate ( k cat ) and the affinity ( K m ) of DAAO were 6.71 s −1 and 33 mM at pH 8.0, respectively, suggesting that optimal pH condition enhanced the activity of DAAO towards L-Pro. Similar results were obtained when L-Ala (pH 9.8), L-Arg (pH 6.5), L-Phe (pH 9.0), L-Thr (pH 9.4), and L-Val (pH 8.5) were catalyzed by DAAO at various pH values. The racemization of the L-amino acids was not found by capillary electrophoresis analysis during oxidation, and quantification analysis of L-amino acids before and after catalytic reaction was performed, which confirmed that the modulation of enantioselectivity of DAAO resulted from the oxidation of L-amino acids rather than D-amino acids by changing pH. A mechanistic model was proposed to explain enhanced activity of DAAO towards L-amino acids under optimal pH condition.

研究领域: 生物化学 · 酶学
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Journal of Magnetic Resonance Open · 2025 · IF 2

Chiral recognition of some D and L-amino acids by microcrystalline cellulose assisted diffusion-ordered NMR spectroscopy

Bowen Han,Jing He,Shaohua Huang

Chiral amino acids play an indispensable role in living organisms. Diffusion-ordered NMR spectroscopy is an effective NMR tool and a noninvasive analytical method for the analyses of mixture without the need for physical separation of the analytes. However, conventional diffusion-ordered NMR spectroscopy method usually fails to resolve the mixtures of chiral amino acids because of their same molecular masses, sizes, and shapes. Microcrystalline cellulose has been gradually gained more and more interest owing to its wide compatibility, surface area, excellent separation efficiency, non-toxicity, cost-effective, and mechanical stability in many fields. Herein we provide a fast, simple, specific and sensitive method to resolve some D and L-amino acids mixtures by using microcrystalline cellulose as a matrix. This work recognized some D and L- proteinogenic amino acid enantiomers with diffusion-ordered NMR for the first time.

CAS / MDL: 9004-34-6
研究领域: 分析化学 · 生物化学
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CHEMICAL ENGINEERING JOURNAL · 2025 · IF 13.2

Effects of alkaline pretreatment on the distribution of amino acid enantiomers and their biofunctions during the anaerobic digestion of waste activated sludge

Hui Liu,Huiting Xu,Zhaofeng Song,Zhengwen Li,Saiwei Zhang,Yili Zhang,Jixiang Wang,Xiaoyong Qian

The types and concentrations of L- and D-type amino acids (AAs) produced by sludge hydrolysis increased with increasing pH of alkali treatment, with the highest content of cysteine and a higher degree of racemization of threonine, cysteine, and alanine. There was a strong correlation between methane production and the following AAs (D-leucine, D-aspartic acid, L-threonine, and L-cysteine). The addition of representative AAs (L-cysteine and D-cysteine) increased cumulative methane production, and L-type promoted better than D-type, with the highest cumulative methane production 906.3 mL/g-VS with the addition of 50 mg/L of L-cysteine, which was 1.20 times that of the CK group (digestion time 21 d); while the methane production with the addition of 200 mg/L of L-cysteine would be inhibited. The L-type AAs promoted better than the D-type in the solubilization, hydrolysis, acidification, and hydrogen-consumption methanogenesis stages, whereas the homoacetogenesis process and acetate-consumption methanogenesis stages did not play a significant role. The dominant genera of bacteria at the genus level belonged to unclassified_c_Acitinobacteria, unclassified_p_Chloroflexi, unclassified_c_Acidimicrobiia and Mycobacterium, while Methanothrix and Methanobacterium were the dominant archaea in the digesters. The top 4 metabolic functions were biosynthesis of secondary metabolites, microbial metabolism in diverse environments, biosynthesis of AAs and carbon metabolism. Metagenome results showed that, with L-cysteine addition, enriching Methanothrix and Methanobacterium showed enhanced contribution to the main pathways, especially the biosynthesis of secondary metabolites and carbon metabolism.

研究领域: 环境科学 · 微生物学 · 生物化学
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