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MICROCHEMICAL JOURNAL · 2021 · IF 4.821

Synergistic effects of chitosan and DNA self-assembly films on the chiral discrimination of tryptophan enantiomers

Yi-xin Sun,Jia-hui He,Dan-dan Zhang,Yang Sheng,Defeng Xu,Rong Zhang,Mark Bradley

The rational design of electrochemical methods for chiral recognition is a focus of research in the detection fields of biomolecules and pharmaceuticals. In this work, electrochemical chiral interface based on chitosan (CS) and deoxyribonucleic acid (DNA) was constructed with self-assembly technology, and then characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), cyclic voltammetry, and electrochemical impedance spectroscopy. The FT-IR and SEM results showed the spatial structure of DNA and CS changed significantly and formed superhelix structure during the self-assembly process. Differential pulse voltammetry (DPV) results showed that the oxidation peak current ratio of D -Trp to L -Trp (I D /I L ) was observed to be 4.02 at 25 °C due to the synergistic effects of CS and DNA, obviously higher than that on any individual CS or DNA modified electrode. In addition, there was a linear relationship between the peak current and Trp enantiomer concentration in the range of 0.005–0.15 mM, and the detection limits of D-Trp and L-Trp were 1.33 and 1.67 µM, respectively. More importantly, the chiral interface can also be used to identify the percentage of D-Trp in non-racemic Trp enantiomers mixture solutions, showing its effectiveness and promising potential in practical applications.

研究领域: 生物化学 · 分析化学 · 电化学
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ANALYTICA CHIMICA ACTA · 2013 · IF 4.387

Visual chiral recognition of tryptophan enantiomers using unmodified gold nanoparticles as colorimetric probes

Lin Zhang,Chunli Xu,Cunwei Liu,Baoxin Li

A simple protocol to distinguish enantiomers is extremely intriguing and useful. In this study, we propose a low-cost, facile, sensitive method for visual chiral recognition of enantimers. It is based on the inherent chirality of gold nanoparticles (AuNPs), and the unmodified AuNPs are used as chiral selector for d - and l -Tryptophan (Trp). In the presence of d -Trp, an appreciable red-to-blue color change of AuNPs solution can be observed, whereas no color change is found in the presence of l -Trp. The method can be used to detect d -Trp in the range of 0.2–10   μM, and the limit of detection is 0.1   μM. The chiral assay described in this work is easily readout with the naked eye or using a UV-vis spectrometer. Furthermore, the AuNPs can selectively adsorb d -Trp, and simple centrifugation can allow the precipitation of d -Trp with AuNPs and leave a net excess of the other enantiomer in solution, thus resulting in enantioseparation. In this method, AuNPs do not need any labeling or modifying with chiral molecules. The method is more attractive because of its high sensitivity, low cost, ready availability and simple manipulation.

研究领域: 分析化学 · 纳米科技 · 生物化学
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Materials Science & Engineering C-Materials for Biological Applications · 2020 · IF 5.88

Nafion-stabilized black phosphorus nanosheets-maltosyl-β-cyclodextrin as a chiral sensor for tryptophan enantiomers

Jiao Zou,Jin-Gang Yu

In this work, we have fabricated nafion (NF) stabilized black phosphorus nanosheets (BPNSs) and 6-O-α-maltosyl-β-cyclodextrin (G2-β-CD) composite (BPNSs-G2-β-CD) as novel electrochemical sensoring platform for chiral recognition of tryptophan (Trp) enantiomers. BPNSs-G2-β-CD composite modified glassy carbon electrode (BPNSs-G2-β-CD/GCE) was further coated with NF which served as a protective film to immobilize BPNSs-G2-β-CD on the electrode surface to achieve high stability. Under the optimum conditions, the oxidation peak current ratio of L-Trp to D-Trp (I L /I D ) and the difference between the peak potential (ΔEp = E D - E L ) were observed to be 1.49 and 20 mV at NF/BPNSs-G2-β-CD/GCE by square wave voltammetry (SWV). In addition, a linear calibration curve could be obtained for peak current versus Trp enantiomers in the concentration range 0.01–1.00 mM with detection limits of 1.07 μM and 1.71 μM for L-Trp and D-Trp (signal-to-noise ratio of 3, S/N = 3), respectively. The chiral recognition mechanism was also proposed, and the intermolecular hydrogen bonding interactions as well as the hydrophobic-cavity-triggered embedding effect dominated the effective chiral recognition. Moreover, the proposed NF/BPNSs-G2-β-CD/GCE showed excellent stability, good reproducibility and anti-interference capability. Therefore, the designed chiral sensor is expected to be practically applied for the sensitive recognition of Trp enantiomers in real samples.

研究领域: 分析化学 · 生物医学工程
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CHEMICAL RESEARCH IN CHINESE UNIVERSITIES · 2023 ·Vol. 39 ·期 6 ·976-984 · IF 3.1

Electrochemical Chiral Recognizing Tryptophan Enantiomers Based on Chiral Metal-Organic Framework D-MOF

Hou Huipeng,Tang Shanshan,Wang Wei,Liu Miao,Liang Axin,Xie Bingteng,Yi Yue,Luo Aiqin

I n this work, an electrochemical chiral sensor of a nanowire-like chiral metal-organic framework/multiwalled carbon nanotube-chitosan/glassy carbon electrode( D -MOF/MWCNTs-CS/GCE) was proposed for the enantiorecognition of L / D -tryptophan( L / D -Trp). The asymmetrical spatial structure of D -MOF provides the feasibility for the enantiorecognition of Trp enantiomers. Moreover, differential pulse voltammetry(DPV) was carried out to be the detection method and the DPV peak potential difference(Δ E p ) between L -Trp and D -Trp was referred as the index of the enantiorecognition performance. Several parameters, such as mass ratios and drop-coated volume of MWCNTs-CS, drop-coated volume and concentration of D -MOF, pH and detection temperature of D -MOF/MWCNTs-CS/GCE were optimized for the largest Δ E p value. And the molecular dynamics(MD) simulation was used to elucidate the enantiorecognition mechanism. Furthermore, the proportions of D -Trp( D -Trp%) in Trp mixtures were detected in a good linear relationship with the DPV peak potentials( E p ), and the proposed electrochemical chiral sensor exhibited good reproducibility, stability and enantiorecognition ability. Additionally, the proposed electrochemical chiral sensor( D -MOF/MWCNTs-CS/GCE) has a good application prospect in the fields of biomedicine, clinical diagnosis, chemical production, pharmaceuticals safety and so on.

研究领域: 分析化学 · 生物医学 · 电化学
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JOURNAL OF ELECTROANALYTICAL CHEMISTRY · 2021 · IF 4.464

Grain-like chiral metal-organic framework/multi-walled carbon nanotube composited electrosensing interface for enantiorecognition of Tryptophan

Xiaofeng Wei,Lishang Li,Huiting Lian,Xuegong Cao,Bin Liu

Due to the widespread application of chiral substances in current society, the electrochemical strategy to assemble chiral metal–organic frameworks (CMOFs) as sensors has shown great potential for sensitive enantiorecognition. In this paper, an efficient and highly selective electrochemical sensor was proposed based on multi-walled carbon nanotube (MWCNT) and CMOF, and successfully achieved sensitive chiral recognition of Tryptophan (Trp) enantiomers . Numerous MOFs in multiple synthesis conditions were investigated for a regular process to access the electrochemical chiral recognition. A variety of amino acids were introduced into the MOFs skeleton by a simple hydrothermal method for the enantio -specificity. Meanwhile the MWCNT smoothly integrated with the CMOF to form a functional electrosensing interface with the increase of conductivity. Based on the current ratio ( R cp ) of tryptophan enantiomers by different modified electrodes , a series of experimental conditions were optimized for the optimal chiral recognition performance of the CMOF/MWCNT-based sensor, finally reaching 2.9 times of ΔI L/D between enantiomers. In addition, D/ l -Trp showed a good linear relationship with the current in the range from 0.4 μM to 19 μM with the detection limit of 0.11 μM for l -Trp and 0.16 μM for d -Trp. The prepared composite-functionalized sensor owned the desired reproducibility and selectivity to identify Tryptophan enantiomers with robust chiral recognition. The research on the structure–activity relationship of chiral MOFs to Tryptophan enantiomers provides a new path to construct more electrochemical sensors for the application of enantiorecognition in pharmaceutical analysis.

研究领域: 分析化学 · 生物医学 · 材料科学
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