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JOURNAL OF ELECTROANALYTICAL CHEMISTRY · 2022 · IF 4.598

A chiral sensing platform based on chiral metal-organic framework for enantiodiscrimination of the isomers of tyrosine and tryptophan

Ning Liu,Baozhu Yang,Zheng-Zhi Yin,Wenrong Cai,Junyao Li,Yong Kong

Chiral metal–organic framework (ZIF-8) was successfully prepared through a two-step electrodepostion method by using l -histidine ( l -His) as the chiral source, and the resultant chiral ZIF-8 ( l -His-ZIF-8) was used for enantiodiscrimination of the isomers of tyrosine (Tyr) and tryptophan (Trp). Although the isomers of both Tyr and Trp could be well discriminated by the l -His-ZIF-8 modified electrode, they displayed opposite voltammetric behaviors on the differential pulse voltammograms (I D-Tyr  > I L-Tyr ; I D-Trp  < I L-Trp ), which could be explained by density functional theory (DFT). Finally, both the pH and the electrodeposition time were optimized to obtain the highest recognition efficiency of the l -His-ZIF-8 modified electrode toward the isomers of Tyr and Trp.

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MICROCHEMICAL JOURNAL · 2021 · IF 4.821

A facile electrochemical chiral sensor for tryptophan enantiomers based on multiwalled carbon nanotube/hydroxypropyl-β-cyclodextrin functionalized carboxymethyl cellulose

Jie Ji,Lihang Qu,Zhongrui Wang,Guangyao Li,Wei Feng,Guang Yang

The development of facile and convenient sensors for the chiral recognition of enantiomers is of great significance for medical and life science. Herein, a sensitive electrochemical sensor for the chiral recognition of tryptophan (Trp) enantiomers was developed based on the assembly of cellulose grafted with hydroxypropyl-β-cyclodextrins (CMC-CD), multi-walled carbon nanotubes (MWCNTs) and copper ions on the surface of a GCE. The morphologies and electrochemical behaviors of the prepared electrode (GCE/MWCNTs/CMC-CD-Cu) were characterized by differential pulse voltammetry (DPV), FT-IR, XPS, cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS). The oxidation peak current ratio (I L /I D ) of DPV could be reached at 2.2 under the optimal experimental conditions. Compared with D-Trp, the higher electrochemical signal of L-Trp was ascribed to the stronger affinity for L-type tryptophan. Additionally, the as-prepared chiral sensor was successfully utilized to analyze the amount of D-Trp in the racemic mixture.

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MICROCHIMICA ACTA · 2021 ·Vol. 188 ·期 5 ·1-13 · IF 5.833

An electrochemical chiral sensor based on the synergy of chiral ionic liquid and 3D-NGMWCNT for tryptophan enantioselective recognition

Liu Nijuan,Liu Jingjing,Niu Xiaohui,Wang Jia,Guo Ruibin,Mo Zunli

A facile chiral composite (3D-NGMWCNT@(S,S)-CIL) was prepared by integrating three-dimensional N-doped graphene oxide multi-walled carbon nanotubes (3D-NGMWCNT) and chiral ionic liquid ((S,S)-CIL) via electrodeposition. SEM, XRD, XPS, and electrochemical methods were used to characterize this composite and it revealed that the integrated 3D-NGMWCNT@(S,S)-CIL composite showed excellent electrochemical performance. Therefore, a 3D-NGMWCNT@(S,S)-CIL/GCE electrochemical sensor was constructed for enantioselective recognition of Trp enantiomers. The coefficient ( I L / I D ) of the 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor was 2.26 by differential pulse voltammograms (DPV), revealing that the synthesized 3D-NGMWCNT@(S,S)-CIL had a higher affinity for L-Trp than D-Trp. Moreover, UV-V is spectroscopy and a water contact angle test also proved this result. The 3D-NGMWCNT@(S,S)-CIL/GCE sensor had a detection limit of 0.024 μM and 0.055 μM, and sensitivity of 62.35 μA·mM −1 ·cm −2 and 30.40 μA·mM −1 ·cm −2 for L-Trp and D-Trp, respectively, with a linear response range of 0.01 to 5 mM. In addition, the 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor showed excellent stability, and good reproducibility and was applied to detect L-Trp or D-Trp in real samples. The novel 3D-NGMWCNT@(S,S)-CIL/GCE chiral sensor provides an efficient and convenient strategy for chiral enantioselective recognition. Graphical abstract Schematic construction of the 3D-NGMWCNT@(S,S)-CIL/GCE chiral electrochemical sensors

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Journal of Functional Foods · 2020 · IF 3.701

Nattokinase mitigated dextran sulfate sodium-induced chronic colitis by regulating microbiota and suppressing tryptophan metabolism via inhibiting IDO-1

Lvqi Zhou,Ning Hao,Xiaotian Li,Jiaxi Chen,Runyu Yang,Changqin Song,Yang Sun,Qi Zhang

In this study, we investigated the protective effect of Nattokinase (NK), the most active ingredient in natto used for healthcare, on dextran sulfate sodium (DSS)-induced chronic colitis and unraveled the potential mechanisms. NK dramatically attenuated clinical symptoms and pathological damage of DSS-induced chronic colitis. NK also inhibited proinflammatory cytokines production in DSS-induced colonic tissues. Mucosal integrity was maintained by NK. Moreover, nattokinase reversed DSS-induced decline of bacteria community diversity and intestinal microbial imbalance by decreasing levels of Firmicutes and increasing levels of Bacteroidetes . Tryptophan (Trp) metabolism analysis demonstrated that NK suppressed Trp catabolism especially the Kynurenine (Kyn) pathway in chronic colitis. Furthermore, NK strikingly down-regulated the protein expression of IDO-1 in chronic colitis mice. Taken together, the study demonstrated that NK relieved DSS-induced chronic colitis by regulating gut microbiota and suppressing Trp metabolism via inhibiting IDO-1. This study indicated that NK might be a promising and effective agent for IBD.

CAS / MDL: 56-69-9
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Aquaculture Reports · 2023 · IF 3.7

Dietary nicotinic acid promotes the growth and tryptophan metabolome of Chinese mitten crab (Eriocheir sinensis) through ACMSD and NADs

Hao-kun Hua,Hui-xing Guo,Wen-bin Liu,Zi-shang Liu,Chao-fan He,Wan-ting Du,Yang-yang Huang,Wei Xiong,Li-ren Ding,Guang-zhen Jiang

This paper did research on the effect of dietary nicotinic acid (NA) on lipid metabolism and tryptophan metabolome of Chinese mitten crab ( Eriocheir sinensis ) to promote its growth. Three diets to administer to E. sinensis (37.25 ± 0.5 g), respectively, for 10 weeks were designed to contain 0% NA (control), 0.02% NA, and 0.10% NA. According to the results, when feeding crabs with 0.02% NA diet, the specific growth rate (SGR) increased markedly while the feed conversion ratio (FCR) was the opposite compared with 0% NA group. The content of total cholesterol (T-CHO) and low-density lipoprotein cholesterol (LDL) in hemolymph decreased significantly when feeding crabs with 0.02% NA diet while the content of high-density lipoprotein cholesterol (HDL) was the opposite. In addition, the relative expression level of microsomal triglyceride transfer protein ( mttp ) and kynureninase ( KFase ) decreased significantly in 0.10% NA group while the relative expression level of sterol regulatory element-binding protein 1 ( srebp-1 ) and nicotinamide adenine dinucleotide synthetase ( NADs ) increased significantly in 0.02% NA group. Meanwhile, the protein expression of 2-amino-3-carboxymuconic semialdehyde decarboxylase (ACMSD) in 0.02% NA group had a very significant increase compared with the other two groups. The result of tryptophan metabolome in hepatopancreas indicates that 0.02% NA in the diet could inhibit the downstream metabolic pathway of tryptophan. According to the results of this research, 0.02% NA in the diet can improve the growth and tryptophan metabolome through ACMSD and NADs , and lipid metabolism is also improved in this group, while 0.10% NA in the diet has no effect on crabs in growth performance.

CAS / MDL: 73-22-3 65-61-2
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Urolithin A Alleviates Colitis in Mice by Improving Gut Microbiota Dysbiosis, Modulating Microbial Tryptophan Metabolism, and Triggering AhR Activation

Mingxia Ma,Yanxin Wang,Siqing Fan,Yumeng Huang,Xiurong Su,Chenyang Lu

Urolithin A (UroA) is a microbial metabolite derived from ellagitannins and ellagic acid with good bioavailability. In this study, we explored the anticolitis activity of UroA and clarified the mechanism by 16S rDNA sequencing and metabonomics. UroA alleviated dextran sulfate sodium (DSS)-induced colitis in mice, characterized by a decreased disease activity index, increased colon length, and improved colonic histopathological lesions, along with inhibited phosphorylation of the mitogen-activated protein kinase signaling pathway. In addition, UroA improved gut microbiota dysbiosis and modulated the microbiota metabolome. Furthermore, targeted metabolomics focused on tryptophan catabolites showed that UroA significantly increased the production of indole-3-aldehyde (IAld) and subsequently led to increased colonic expression of aryl hydrocarbon receptor (AhR) and promoted the serum content of IL-22 in mice with colitis. Collectively, our data identified a novel anticolitis mechanism of UroA by improving gut microbiota dysbiosis, modulating microbial tryptophan metabolism, promoting IAld production, and triggering AhR/IL-22 axis activation. However, a limitation noted in this study is that these beneficial effects of UroA were found at 50 μM in vitro and 20 mg/kg in vivo, which were nonphysiological concentrations.

CAS / MDL: 119-90-4
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JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS · 2023 ·Vol. 34 ·期 11 ·1-15 · IF 2.8

β-Cyclodextrin dinuclear copper supported on graphene/polypyrrole nanocomposites as an electrochemical sensor for enantioselectivity recognition of tryptophan enantiomers

Zhang Zengdong,Wang Jia,Pei Hebing,Guo Ruibin,Liu Nijuan,Mo Zunli

Electrochemical chiral recognition has gained much of attention as an efficient method for enantiomeric recognition. Herein, a chiral sensing platform via β-cyclodextrin dinuclear copper (Cu-β-CD) as a chiral selector supported on graphene/polypyrrole (RGO/Ppy) nanocomposites were fabricated for recognition of tryptophan (Trp) enantiomers. Cu-β-CD with additional chiral sites improves recognition efficiency, and the addition of the conducting polymer Ppy enhances the electrical conductivity of the nanocomposite and addresses the agglomeration effect of graphene (RGO). In addition, the composition and morphology of the materials were analyzed by transmission electron microscopy (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR) and X-ray photoelectron spectroscopy (XPS). The mechanism of chiral recognition was evaluated by water contact angle experiments and UV–Vis absorption spectroscopy. And the battery of chiral recognition experiments revealed that the chiral sensing platform RGO/Ppy/Cu-β-CD/GCE provides excellent recognition of the Trp enantiomer with an enantioselectivity coefficient of 3.24. It also exhibits outstanding stability and reproducibility, with a minimum line of detection (LOD) of 0.37 mM and 1.05 mM for L-Trp and D-Trp, respectively. With these results, the RGO/Ppy/Cu-β-CD/GCE chiral sensing platform has provided a feasible approach for the electrochemical chiral recognition of Trp enantiomers.

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ACTA PHARMACOLOGICA SINICA · 2025 · IF 8.4

Cannabinoid-2 receptor depletion promotes non-alcoholic fatty liver disease in mice via disturbing gut microbiota and tryptophan metabolism

Cheng Wei-ting,Pei Si-ya,Wu Jie,Wang Yan-jie,Yang Yong-wen,Xiao Mei-fang,Chen Jun,Wang Yuan-yuan,Wu Li,Huang Ze-bing

Non-alcoholic fatty liver disease (NAFLD) is the hepatic manifestation of the metabolic syndrome. NAFLD encompasses a spectrum of liver damage starting with liver steatosis and lipid disorders presented as the hallmark. Cannabinoid-2 receptor (CB2R) is the receptor of endocannabinoids mainly expressed in immune cells. Our preliminary study revealed the preventative role of CB2R in liver injury related to lipid metabolism. In this study, we aimed to explore the role of CB2R in NAFLD and the underlying mechanism related to microbial community. High-fat diet-induced NAFLD model was established in mice. We found that hepatic CB2R expression was significantly reduced in NAFLD mice and CB2R –/– mice fed with normal chow. Interestingly, cohousing with or transplanted with microbiota from WT mice, or treatment with an antibiotic cocktail ameliorated the NAFLD phenotype of CB2R –/– mice. The gut dysbiosis in CB2R –/– mice including increased Actinobacteriota and decreased Bacteroidota was similar to that of NAFLD patients and NAFLD mice. Microbial functional analysis and metabolomics profiling revealed obviously disturbed tryptophan metabolism in NAFLD patients and NAFLD mice, which were also seen in CB2R –/– mice. Correlation network showed that the disordered tryptophan metabolites such as indolelactic acid (ILA) and xanthurenic acid in CB2R -/- mice were mediated by gut dysbiosis and related to NAFLD severity indicators. In vitro and in vivo validation experiments showed that the enriched tryptophan metabolites ILA aggravated NAFLD phenotypes. These results demonstrate the involvement of CB2R in NAFLD, which is related to gut microbiota-mediated tryptophan metabolites. Our findings highlight CB2R and the associated microbes and tryptophan metabolites as promising targets for the treatment of NAFLD.

CAS / MDL: 1821-52-9
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JOURNAL OF NANOPARTICLE RESEARCH · 2016 ·Vol. 18 ·期 7 ·1-9 · IF 2.101

l-Tryptophan-capped carbon quantum dots for the sensitive and selective fluorescence detection of mercury ion in aqueous solution

Wan Xuejuan,Li Shifeng,Zhuang Lulu,Tang Jiaoning

l -Tryptophan-capped carbon quantum dots ( l -CQDs) were facilely synthesized through “green” methodology, and the obtained material was utilized as a sensitive and selective fluorescence sensor for mercury ion (Hg 2+ ) in pure aqueous solutions. Carboxyl-functionalized CQDs were first green synthesized by a one-step hydrothermal route, and l -tryptophan was then attached to CQDs via direct surface condensation reaction in aqueous solution at room temperature. The as-synthesized l -CQDs had an average size of ca. 5 nm with a good dispersity in water, and exhibited a favorable selectivity for Hg 2+ ions over a range of other common metal cations in aqueous solution (10 mM PBS buffer, pH 6.0). Upon the addition of Hg 2+ , a complete fluorescence quenching (ON–OFF switching) of l -CQDs was evident from the fluorescence titration experiment, and the fluorescence detection limit of Hg 2+ was calculated to be 11 nM, which indicated that the obtained environmentally friendly l -CQDs had sensitive detection capacity for Hg 2+ in aqueous solution.

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Journal of Physical Chemistry C · 2015 · IF 4.772

Chiral Recognition of d-Tryptophan by Confining High-Energy Water Molecules Inside the Cavity of Copper-Modified β-Cyclodextrin

Yongxin Tao,Xiaogang Gu,Linhong Deng,Yong Qin,Huaiguo Xue,Yong Kong

We report a Cu2+-modified β-cyclodextrin, Cu2-β-CD, that was self-assembled on poly(l-glutamic acid) (P-l-Glu) for chiral recognition of d-tryptophan (d-Trp). Cu2+ formed binuclear hydroxy-bridge (Cu(OH)2Cu) at the wider opening of the cavity of β-CD and acted as a cap to prevent high-energy water molecules from being released while forcing Trp isomers to enter through its narrower opening. Because H-bonds were favored to form between the high-energy water molecules and the amino groups of d-Trp inside the cavity of β-CD, d-Trp was thus recognized. The recognition capability of the Cu2-β-CD appeared to depend on the way the Cu2-β-CD self-assembled onto P-l-Glu, preferring via H-bonds rather than via electrostatic interactions, because electrostatic interactions between P-l-Glu and Cu(OH)2Cu could alter the configuration of the Cu2-β-CD cavity, resulting in weakened H-bonds between high-energy water molecules and d-Trp.

CAS / MDL: 73-22-3 153-94-6
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FOOD CHEMISTRY · 2024 · IF 8.5

Molecular simulation screening and sensory evaluation unearth a novel kokumi compound with bitter-masking effect: N-lauroyl-L-tryptophan

Lei Cai,Liyu Li,Xu Zhao,Lu Wang,Yuqin Cheng,Wenxiang Gao,Chun Cui

N-lauroyl-L-tryptophan (LT), which has the strongest potential flavor-presenting activity, was skillfully screened from numerous N-Lau-AAs docked to different taste receptors by molecular simulation techniques. Subsequently, LT was synthesized employing food-grade commercial enzymes and structurally characterized, the optimized yields of LT could reach 69.08%, 76.16%, and 50.40%, respectively. Sensory and E -tongue evaluations showed that LT at 1 mg/L significantly benefited the performance of different taste sensations and exhibited different bitter taste masking effects: L-Ile (68.42%), L-Trp (68.18%), D-salicylic acid (48.48%) and quinine (35.00%). The molecular docking results illustrated that LT had a high affinity for various taste receptors , dominated by hydrogen bonding and hydrophobic interactions. This work provided a rare systematic elucidation of the potential and mechanism of enzymatically synthesized LT in enhancing taste properties. It provides novel insights into the directions and strategies for the excavation and innovation of flavor enhancers and food flavors.

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CHEMICAL ENGINEERING JOURNAL · 2025 · IF 13.2

Development of multifunctional bacterial cellulose film modified with polymeric tryptophan-anion-based imidazolium ionic liquid for enhanced berry preservation

Wenqi Song,Jingtao Liu,Sufeng Zhang,Zongcheng Miao,Yuzhen Zhao,Zemin He,Qin Peng,Valentin Nica,Liwei Qian

Water loss, oxidation, and microbial infection can degrade berries, highlighting the need for versatile, eco-friendly packaging. A novel tryptophan-Anion-Based ionic liquid modified reagent, 1-vinyl-3-aminopropyl imidazole-tryptophan ([vaim][Trp]), was synthesized and utilized for crafting a multifunctional bacterial cellulose (BC) packaging film (BC-CTA@PIL) via grafting polymerization. The optimized BC-CTA@PIL showcased superior tensile strength (5.42 MPa), modulus (152.24 MPa), oxygen and water vapor barrier capabilities due to the multiple interactions between polymeric [vaim][Trp] chains and BC macromolecules. Owing to the aromatic heterocyclic structure present in [vaim][Trp], the BC-CTA@PIL can achieve a free radical scavenging rate of 67.78 %. The multi-amino and hydrophobic functional groups within the polymeric [vaim][Trp] of BC-CTA@PIL synergistically contribute to its antibacterial efficacy, with inhibition rates of over 95 % against four Gram negative and positive bacterial strains. The BC-CTA@PIL revealed a high cell survival rate of 93.03 % for hamster lung cells. Therefore, BC-CTA@PIL could effectively preserving moisture and nutrients in berries, thereby extending their shelf life.

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