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ENZYME AND MICROBIAL TECHNOLOGY · 2024 · IF 3.4

Biomanufacture of L-homoserine lactone building block: A strategy for preparing γ-substituted L-amino acids by modular reaction

Yuguang Wang,Mengjing Wu,Huifang Zheng,Dongmei Wu,Panpan Yao,Wenjing Li,Kexin Jin,Xinjun Yu

A strain high-performance of esterase producing bacteria was screened from soil, which could selectively hydrolyze D -homoserine lactone from its racemate to achieve the resolution of L - homoserine lactone with more than 99% e.e. in 48% yield. L -homoserine lactone building block was then converted to L -α-amino-γ-bromobutyronic acid chiral blocks, which reacted with various nucleophilic reagent modules could to be applied to prepare L -γ- substituted α-amino acids such as L -selenomethionine, L -methionine, L -glufosinate and L -selenocystine. Its advantages included high selectivity of biocatalytic resolution reactions, high optical purity of products, racemic recycle of D -substrates and modular reaction, which simplified the production process of these products and highlighted the power of biological manufacturing.

CAS / MDL: 6305-38-0 24424-99-5
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RSC Advances · 2016 ·Vol. 6 ·期 77 ·73699-73708 · IF 3.289

Preparation and characterization of foamy poly(γ-benzyl-L-glutamate-co-L-phenylalanine)/bioglass composite scaffolds for bone tissue engineering

Ning Cui,Junmin Qian,Jinlei Wang,Chuanlei Ji,Weijun Xu,Hongjie Wang

In this study, novel foamy scaffolds of poly(γ-benzyl-L-glutamate) (PBLG) and poly(γ-benzyl-L-glutamate-co-L-phenylalanine) (P(BLG-PA)) were fabricated via a combination of a sintered NaCl templating method and ring-opening polymerization of α-amino acid N-carboxyanhydrides. The obtained polypeptide-based scaffolds displayed a foamy structure and had a desirable glass transmission temperature (23.2–44.6 °C), contact angle (78.5–88.5°), compression modulus (56.3–110.2 kPa) and degradation time (>8 weeks). MC3T3-E1 cells were used to test the in vitro biocompatibility, and we found that PBLG scaffolds could significantly promote cell viability and proliferation compared to P(BLG-PA) scaffolds. In addition, micro-scale bioglass particles (BG) were incorporated into PBLG to form a porous scaffold, namely PBLG/BG composite scaffolds, which further enhanced the cell viability and adhesion, as confirmed by live-dead staining and SEM observation. The results of the ALP activity assay suggested that PBLG/BG composite scaffolds could promote the osteogenic differentiation of MC3T3-E1 cells. The results of histology analysis showed that the PBLG/BG composite scaffolds rather than PBLG scaffolds significantly promoted connective tissue and vascular ingrowth. The results obtained using digital radiography technology showed that PBLG/BG composite scaffolds significantly improved osteogenesis in vivo. In summary, our results indicated that PBLG/BG composite scaffolds could be a promising bioactive substance for bone regeneration.

研究领域: 材料科学 · 生物医学工程 · 组织工程
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EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES · 2026 · IF 5.1

Glycyl-l-histidyl-l-lysine as a novel co-former in co-amorphous systems: Enhanced aqueous solubility and physical stability

Qiang Huang,Zhiren Zou,Dian Cheng,Ruyu Gao,Lin Zhou,Wencheng Wu,Yinyin Yuan,ChangJu Chun,Yuye Huang,Guang Liang,Wenqi Wu

Co-amorphous systems have emerged as a promising strategy to enhance the aqueous solubility of poorly water-soluble drugs. Although amino acids have been widely studied as co-formers, some amino acid-based co-amorphous systems exhibit limited dissolution improvement and inadequate physical stability. In this study, glycyl- l -histidyl- l -lysine (GHK) was selected as a co-former due to its biocompatibility and multiple functional groups, which were expected to enhance the dissolution and the physical stability of pure amorphous drugs. Basic mebendazole, neutral tadalafil and acidic indomethacin were selected as the model drugs. Glycine, histidine and lysine were used as co-formers for comparison. All drug-co-former combinations were prepared by ball milling at a 1:1 molar ratio. GHK achieved complete amorphization with all three model drugs within 15 min of milling, whereas most amino acid-based mixtures remained partially crystalline even after 60 min of milling. The formation of homogeneous amorphous forms was confirmed by differential scanning calorimetry, indicated by a single glass transition temperature in the drug-GHK system. The drug-GHK systems exhibited significantly enhanced dissolution performance, including faster dissolution rates, higher drug concentration and sustained supersaturation (up to 1440 min) compared to both the pure crystalline and amorphous drugs. Furthermore, physical stability studies confirmed that GHK-based systems maintained amorphous forms for at least 6 months, outperforming both amino acid-based counterparts and pure amorphous drugs. Notably, salt formation and hydrogen bonding were associated with the observed improvements in dissolution performance and physical stability. In conclusion, GHK represents a promising co-former, expanding the design space for co-amorphous systems.

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CHIRALITY · 2015 ·Vol. 27 ·期 9 ·650-657 · IF 1.886

Enantioseparation of Racemic Flurbiprofen by Aqueous Two-Phase Extraction With Binary Chiral Selectors of L-dioctyl Tartrate and L-tryptophan

Zhi Chen,Wei Zhang,Liping Wang,Huajun Fan,Qiang Wan,Xuehao Wu,Xunyou Tang,James Z. Tang

A novel method for chiral separation of flurbiprofen enantiomers was developed using aqueous two-phase extraction (ATPE) coupled with biphasic recognition chiral extraction (BRCE). An aqueous two-phase system (ATPS) was used as an extracting solvent which was composed of ethanol (35.0% w/w) and ammonium sulfate (18.0% w/w). The chiral selectors in ATPS for BRCE consideration were L-dioctyl tartrate and L-tryptophan, which were screened from amino acids, β-cyclodextrin derivatives, and L-tartrate esters. Factors such as the amounts of L-dioctyl tartrate and L-tryptophan, pH, flurbiprofen concentration, and the operation temperature were investigated in terms of chiral separation of flurbiprofen enantiomers. The optimum conditions were as follows: L-dioctyl tartrate, 80 mg; L-tryptophan, 40 mg; pH, 4.0; flurbiprofen concentration, 0.10 mmol/L; and temperature, 25 °C. The maximum separation factor α for flurbiprofen enantiomers could reach 2.34. The mechanism of chiral separation of flurbiprofen enantiomers is discussed and studied. The results showed that synergistic extraction has been established by L-dioctyl tartrate and L-tryptophan, which enantioselectively recognized R- and S-enantiomers in top and bottom phases, respectively. Compared to conventional liquid–liquid extraction, ATPE coupled with BRCE possessed higher separation efficiency and enantioselectivity without the use of any other organic solvents. The proposed method is a potential and powerful alternative to conventional extraction for separation of various enantiomers. Chirality 27:650–657, 2015 . © 2015 Wiley Periodicals, Inc.

研究领域: 手性化学 · 分离科学 · 分析化学 · 制药技术
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Polymers · 2022 ·Vol. 14 ·期 22 ·4902 · IF 4.967

Polymorphic Crystallization Behavior of a Poly(butylene adipate) Midblock within a Poly(L-lactide-butylene adipate-L-lactide) Triblock Copolymer

Lei Hua,Xiaodong Wang

New biodegradable aliphatic PLLA-PBA-PLLA copolymers with soft poly(butylene adipate) (PBA) and hard poly(l-lactide) (PLLA) building blocks were synthesized via ring-opening polymerization (ROP). Proton nuclear magnetic resonance (1HNMR) was utilized to confirm the volume fraction of PBA (fPBA) within PLLA-PBA-PLLA. It was found that a PBA midblock (PBA-mid) within PLLA-PBA-PLLA-s (PLLA-PBA-PLLA triblock copolymer with a short PLLA block length) might display lamellar domain structure. However, PBA-mid within PLLA-PBA-PLLA-l (PLLA-PBA-PLLA triblock copolymer with a long PLLA block length) might locate itself as a nanoscale cylindrical domain surrounded by a PLLA continuous phase. Polymorphic crystals of PBA-mid within the PLLA-PBA-PLLA copolymers were formed after melt crystallization at the given temperatures, which were studied by differential scanning calorimetry (DSC) and wide-angle X-ray diffraction (WAXD) analysis. According to the WAXD and DSC analyses, it was interesting to find that the α-type crystal of PBA-mid was favorable to develop in the lower temperature region regardless of the state (crystallization or amorphous) of the PLLA component. Additionally, when the PLLA component was held in its amorphous state, it was easier for PBA-mid within the PLLA-PBA-PLLA copolymers to transform from the metastable β-form crystal to the stable α-form crystal. Furthermore, polarized optical microscopy (POM) photos provided direct evidence of the polymorphic crystals of PBA-mid within PLLA-PBA-PLLAs.Keywords:biodegradable aliphatic;triblock copolymers;polymorphic crystal

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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

Yolk-shell composite optical sensors with chiral L-histidine/Rhodamine 6G for high-sensitivity “turn-on” detection of L-proline

Yu-Han Geng,Yu Xin,Jing Du,Ming-Yi Cui,Yuan-Yuan Liu,Le-Xi Zhang,Bin Ding

Chirality is a ubiquitous phenomenon in nature and has attracted wide attention in the biomedicine, pharmaceutics and biosensing research fields. Enantiomeric recognition of chiral compounds, especially chiral drugs and chiral amino acids, is important for human health and nutrition. In this work, through the encapsulation of L-His&R6G (L-His = L-Histidine; R6G = Rhodamine 6G) into MOF@MOF framework ZIF-67@ZIF-8, composited material L-His&R6G@ZIF-67@ZIF-8 can be obtained. Additionally, through the etching process, a unique yolk-shell ZIF-8 chiral composite optical sensors L-His&R6G@ZIF-8 ( 1 ) can be successfully prepared. Photo-luminescent (PL) experiment also reveals that 1 can highly sensitively detect L-Proline (L-Pro) through the “turn-on” detection strategy (K BH = 1.22 × 10 4 M −1 and detection limit 1.9 μM). Further yolk-shell L-His&R6G@ZIF-8-based fabricate flexible mixed-matrix membranes has been prepared using doctor-blading technique, which show significant fluorescence enhancement effect under ultraviolet lamp. This work also provides the unique example of preparing chiral yolk-shell framework composite sensors, which have broad application in chiral sensing area.

CAS / MDL: 71-00-1
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POLYMERS & POLYMER COMPOSITES · 2019 · IF 0.683

Effect of chain segment length on crystallization behaviors of poly(l-lactide-b-ethylene glycol-b-l-lactide) triblock copolymer

Yongji Gong,Weihua Song,Yifan Wu,Daohai Zhang,Yufei Liu,Qian Zhao,Min He,Xiaolang Chen

The poly(l-lactide-b-ethylene glycol-b-l-lactide) (PLLA-PEG-PLLA) triblock copolymers with different chain segment length are fabricated by ring-opening polymerization. The structure, molecular weight, and crystallization behaviors of the triblock copolymers are characterized by Fourier transform infrared, nuclear magnetic resonance spectroscopy, gel permeation in chromatography, X-ray diffraction, differential scanning calorimetry, and polarizing optical microscopy (POM). The results show that the increase of block length is beneficial to improve its crystallization. In addition, the triblock copolymer exhibits a double crystallization phenomenon. The POM results indicate that PEG and PLLA chains of the copolymer crystallize in their respective crystallization temperature regions. The growth rate of the PLLA spherocrystal decreases and the dendritic spherocrystals appear with increasing the PEG chain length when the PLLA chain of the copolymer is isothermal crystallized at 80°C and PLLA chain length is constant. The growth rate of the PEG spherocrystal decreases and the spherocrystal morphology changes little with increasing PLLA chain length when the PEG chain is isothermal crystallized at 25°C and the length of PEG chain remained unchanged.

CAS / MDL: 25322-68-3
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ELECTROPHORESIS · 2012 ·Vol. 34 ·期 3 ·409-416 · IF 3.303

Microchip CE-LIF method for the hydrolysis of L-glutamine by using L-asparaginase enzyme reactor based on gold nanoparticle

Juan Qiao,Li Qi,Huijuan Yan,Yaping Li,Xiaoyu Mu

l -Asparaginase ( l -Asnase) can suppress the growth of malignant cells by rapid depletion of two essential amino acids, l -glutamine ( l -Gln) and l -asparagine ( l -Asn). To study the cytotoxic effect and the secondary complications of l -Asnase in the treatment of acute lymphoblastic leukemia, the development of a novel enzyme reactor of l -Asnase for the hydrolysis of l -Gln, employing the enzyme-gold nanoparticle conjugates in capillary, was reported in this work. First, a microchip CE (MCE)-LIF was established for the separation of l -amino acids ( l -Gln and l -glutamic acid) and studying the hydrolysis of l -Gln by using l -Asnase enzyme reactor. Then, using l -Gln as target analyte, the enzyme kinetics of l -Asnase in free solution, enzyme-gold nanoparticle conjugates (E-GNP), and the enzyme-gold nanoparticle conjugates immobilized in capillary (E-GNP-C) were investigated in detail with the proposed MCE-LIF method. Moreover, for optimizing the enzymatic reaction efficiency, three important parameters, including the length of capillary, the enzyme concentration reacted with gold nanoparticle and the amount of l -Asnase immobilized on the gold nanoparticle, have been studied. Owing to the high specific activity, the E-GNP-C enzyme reactor exhibited the best performance for the hydrolysis of l -Gln.

CAS / MDL: 4420-74-0
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NEW JOURNAL OF CHEMISTRY · 2017 ·Vol. 41 ·期 24 ·15216-15228 · IF 3.269

A novel carbon dots derived from reduced L-glutathione as fluorescent probe for the detection of the L-/D-arginine

Xiaoqing Zeng,Lei Zhang,Jidong Yang,Yuan Guo,Yunmei Huang,Haiyan Yuan,Yongsheng Xie

In this report, water-soluble carbon dots (CDs) with stable fluorescence (FL) were designed and synthesized by using environment-friendly reduced L-glutathione (GSH) as the precursor and ethylenediamine (EDA) as the passivating agent through a one-step hydro-thermal method. The CDs, with bright blue FL, had the quantum yield (QY) of 40% and showed excellent monodispersity and solubility in water. The FL intensity was remarkably enhanced when a racemic modification of L-/D-arginine (Arg) was added into the CDs solution. Therefore, the CDs could be considered as a sensitive probe for the detection of Arg. Under optimized conditions, the CDs exhibited a linear fluorescence response in the range of 3–124 μM (R2 = 0.9987) Arg with the detection limit of 2.85 × 10−8 M. In addition, no evident difference was observed when comparing the FL results of L-Arg and D-Arg. Therefore, this method could not be used in the chiral recognition of two enantiomers. Under optimum conditions, the mechanism and the reasons for the enhancement of FL were investigated. The developed method exhibited great stability, selectivity and accuracy in determining the Arg content in human urine sample and the recovery range was from 97.0% to 102.2%. Thus, our proposed method has potential application in biological molecular recognition.

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MICROCHEMICAL JOURNAL · 2024 · IF 4.9

Hydrogen-bond induced enhanced fluorescence sensing of metal organic frameworks for colorimetric l-glutamic acid and l-aspartic acid detection

Zhikun Zhang,Liwei Bai,Heli Tian,Jilong Han,Kunjie Li,Zhengjie Li,Qingju Liu

Fluorescent metal–organic frameworks (FMOFs) hold great promise for detecting biomolecules, but a comprehensive understanding of their response mechanisms is still challenging to guide the design of assays. Herein, we creatively proposed fluorescent analysis via the hydrogen-bond-triggered enhanced fluorescence effect between the oxygen of a carboxyl group of targets and an amino group of ligands in the FMOFs in an aqueous solution. Based on the above strategy, we synthesized the Ru@ZrMOF and constructed a ratiometric fluorescent and colorimetric dual-readout method for a simple and rapid platform to selectively detect amino acids. Taking l -glutamic ( l -Glu) and l -aspartic acid ( l -Asp) as examples, the introduction of l -Glu and l -Asp sharply increased the fluorescent value at 450 nm through strong hydrogen bonding, leading to a difference in the color from red to blue. Data from computational simulations point to the presence of strong hydrogen bonds between l -Glu/ l -Asp and FMOFs. Dual-mode fluorescent/colorimetric method selectively and accurately detects l -Glu acid and l -Asp within 30 min. The detection range for the two was found to be between 5 μM and 2 mM, with detection limits of 3 μM and 2.5 μM, respectively. In addition, a paper-based platform was fabricated and a logic gate was developed for the rapid and visual measurement of l -Glu and l -Asp. This platform is simple, quick, easy to use, and sensitive, making it a promising tool for future applications in amino acid detection, particularly in biological samples.

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INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY · 2024 · IF 5

Widely targeted metabolomics-based analysis of the impacts of L. plantarum and L. paracasei fermentation on rosa roxburghii Tratt juice

You Luo,Ruling Tang,Han Qiu,Angxin Song

Rosa roxburghii Tratt fruits (RRT) exhibit extremely high nutritional and medicinal properties due to its unique phytochemical composition. Probiotic fermentation is a common method for processing fruits. Variations in the non-volatile metabolites and bioactivities of RRT juice caused by different lactobacilli are not well understood. Therefore, we aimed to profile the non-volatile components and investigate the impacts of L. plantarum fermentation (LP) and L. paracasei fermentation (LC) on RRT juice (the control, CG). There were both similarities and differences in the effects of LP and LC on RRT juice. Both of the two strains significantly increased the content of total phenolic, total flavonoid, and some bioactive compounds such as 2-hydroxyisocaproic acid, hydroxytyrosol and indole-3-lactic acid in RRT juice. Interestingly, compared with L. paracasei , L. plantarum showed better ability to increase the content of total phenolic and these valuable compounds, as well as certain bioactivities. The antioxidant capacity and α-glucosidase inhibitory activity of RRT juice were notably enhanced after the fermentations, whereas its cholesterol esterase inhibitory activity was reduced significantly. Moreover, a total of 1466 metabolites were identified in the unfermented and fermented RRT juices. There were 278, 251 and 134 differential metabolites in LP vs CG, LC vs CG, LC vs LP, respectively, most of which were upregulated. The key differential metabolites were classified into amino acids and their derivatives, organic acids, nucleotides and their analogues, phenolic acids and alkaloids, which can serve as potential markers for authentication and discrimination between the unfermented and lactobacilli fermented RRT juice samples. The KEGG enrichment analysis uncovered that metabolic pathways, purine metabolism, nucleotide metabolism and ABC transporters contributed mainly to the formation of unique composition of fermented RRT juice. These results provide good coverage of the metabolome of RRT juice in both unfermented and fermented forms and also provide a reference for future research on the processing of RRT or other fruits.

CAS / MDL: 1898-66-4 28752-68-3
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Sustainability · 2021 ·Vol. 13 ·期 1 ·434 · IF 3.251

Uptake Kinetics of \({\text{NH}_{4}^{+} }\), \({\text{NO}_{3}^{-} }\) and \({\text{H}_{2}\text{PO}_{4}^{-} }\) by Typha orientalis, Acorus calamus L., Lythrum salicaria L., Sagittaria trifolia L. and Alisma plantago-aquatica Linn

Kunlun Wang,Qian Hu,Yumin Wei,Hui Yin,Changhong Sun,Guizhong Liu

The emergent plants may differ in their capacity to assimilate nutrients from eutrophic water bodies, so the utilization of suitable emergent plants is the key part for successful restoration of shallow eutrophic lakes and rivers. This research applied the depletion method to study the kinetics of uptake of nutrient (H2PO4−,NH4+,NO3−) in different nutrient stresses by the five emergent aquatic plants (Acorus calamusL.,Typha orientalis, Lythrum salicariaL.,Sagittaria trifoliaL.,Alisma plantago-aquaticaLinn) in the riverine zones of Dashi River (39°30′–39°40′ N, 115°59′–116°5′ E), a shallow eutrophic river located in Fangshan District, Beijing. The results showed that at the three phosphorus levels,A. calamusandA. plantago-aquaticahad the highest maximum uptake rate values forNH4+under low to moderate phosphorus conditions, and high phosphorus, respectively.T. orientalishad the highest maximum uptake rate values forNO3−at all phosphorus concentrations, while the Michaelis-Menten constant values ofL. salicariaandA. plantago-aquaticawere smaller. At the three nitrogen levels, the maximum uptake rate values forH2PO4−were the greatest forA. plantago-aquaticaat the low to moderate nitrogen levels andL. salicariaat high levels. Meanwhile,T. orientalisandL. salicariahad the smallest Michaelis-Menten constant values. In this study, nitrogen microbial transformations, such as nitrification, denitrification and their coupling were not measured and their role in measuring kinetics was not assessed. Thus, achieved results shall be considered as a synthesis of several processes mediated by plants, a theoretical guidance to the selection of plant species for phytoremediation of polluted water bodies with different nutrient stresses for quality improvement around the diverse rivers in Haihe River basin.Keywords:emergent plants;eutrophication;nitrogen;phosphorus;uptake kinetics;stress

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