JOURNAL OF CHROMATOGRAPHY A
·
2025
·
IF 4
Zixing Wang,Yuxin Fan,Hong Chen,Xiang Chen,Dexuan Cai,Xihao Tang,Shengrun Zheng,Jun Fan,Songliang Cai,Weiguang Zhang
The development of novel chiral stationary phases (CSPs) based on spherical covalent organic frameworks (SCOFs) holds great importance in the field of chiral chromatographic separation. Herein, SCOF-1∼SCOF-4 were synthesized using 1,3,5-tris(4-aminophenyl)benzene (TAPB) as the connecting node and 2,5-dihydroxyterephthalaldehyde (DHTA) with 2,5-dimethoxyterephthalaldehyde (DMTA) as linkers, while controlling the ratio of two linkers. Subsequently, SCOF-3 containing phenolic hydroxyl groups was post-modified by 10-camphorsulfonyl chloride, yielding a derivative SCOF-5 with camphorsulfonyl groups. Besides, a vinyl-functionalized SCOF-6 was synthesized via the reaction of TAPB with 2,5-divinylterephthalaldehyde (DVTA). These SCOFs were then utilized as matrices to coat with the chiral selector cellulose-tris (3,5-dimethylphenylcarbamate) (CDMPC), resulting in the fabrication of six SCOFs@CDMPC CSPs. Their applications in high-performance liquid chromatography (HPLC) for chiral separations were systematically investigated. The results demonstrated that the chiral resolution performances of these CSPs varied depending on the SCOF matrices with different side chains, primarily due to their distinct zeta potentials. As the zeta potentials of the SCOFs matrices increased, the chiral separation capabilities of SCOFs@CDMPC CSPs improved sequentially. Notably, the SCOF-6@CDMPC CSP, prepared from SCOF-6 with the highest zeta potential, exhibited superior chiral separation performance, achieving efficient resolution of chiral compounds including metalaxyl, triticonazole, trans -stilbene oxide and 1-(1-naphthyl)ethanol with highest resolution up to 10.14. This work not only validates the potential of SCOFs as matrices for fabrication of new CSPs but also reveals that the zeta potential of SCOFs matrices is a critical factor influencing their chiral separation performances. These findings provide new insights for the design of advanced SCOFs-based CSPs.
研究领域:
化学
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材料科学
·
分析化学
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PubMed
高影响因子
ANALYTICAL SCIENCES
·
2020
·Vol. 36
·期 6
·687-695
·
IF 2.049
Hui WANG,Yazhou SHUANG,Tianci ZHANG,Liang LI,Laisheng LI
A cholesterol mono-derivatized β-cyclodextrin was synthesized and bonded onto silica gel (SBA-15) to obtain a cholesterol mono-derivatized β-cyclodextrin-bonded stationary phase (CHCDP). The chemical structures of mono-derivatized β-cyclodextrin and CHCDP were characterized by infrared spectroscopy, mass spectrometry, elemental analysis and thermogravimetric analysis, correspondingly. Furthermore, the separation ability of CHCDP in terms of achiral compounds was systematically evaluated by separating benzene homologs, polycyclic aromatic hydrocarbons (PAHs) and some positional isomers. As a result, CHCDP completely separated five benzene homologs and nine PAHs within 30 min under the reversed-phase. In addition, the chiral chromatographic property of CHCDP was also evaluated by separating some racemic compounds including flavanones, triazoles, β-blockers, etc. The results showed that the CHCDP exhibited high enantioselectivities towards most of selected analytes. The enantioresolutions were in the range from 1.43 to 2.51 on CHCDP. Especially the resolutions of 2′-hydroxyflavanone, hexaconazole, Dns-serine and atenolol were as high as 1.94, 1.91, 2.15 and 1.57, respectively. Obviously, the CHCDP was a versatile stationary phase with chiral and achiral separation capabilities in multi-mode chromatography, which was related to the introduction of cholesterol to the port of cyclodextrin, enhancing the hydrophobic interaction of cyclodextrin with achiral compounds, while maintaining the inclusion complexation of it with chiral compounds as well.
研究领域:
分析化学
·
色谱技术
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DOI
PubMed
高影响因子
TALANTA
·
2025
·
IF 6.1
Mo Chen,Yuanyuan Hou,Xinyu Liang,Fuquan Zhao,Liming Bai,Hongtao Chu,Shili Qin,Ming Zhao,Lidi Gao,Shuren Liu
In this work, two metal-organic porous materials from the two imidazole-based ligands (4-methylimidazole-5-carbaldehyde (aImeIm) and histidine (His)) and the same metal source (Zn(CH 3 COO) 2 ·2H 2 O), namely His-ZIF-93 with a crystal zeolite imidazolate framework and His/aImeIm@Zn with an amorphous networks, were first designed and synthesized by the one-pot method. They were used as the stationary phases (SPs) of open-tubular capillary electrochromatography (OT-CEC) to evaluate and compare their separation performance for the nonchiral and chiral compounds. His-ZIF-93-bonded OT-CEC column successfully separated five families of nonchiral analytes due to the synergistic effect of His and the crystal framework. The separation mechanism included electrostatic interaction, molecular sieve effect, π-π interaction, electrophoretic mobility, hydrogen bonding interaction, and so on. His/aImeIm@Zn-bonded OT-CEC column exhibited a more superior enantioseparation capability for seven chiral compounds with an ultrahigh column efficiency of 7.6 × 10 5 plates/m due to a large number of chiral sites and the porous networks. Enantioseparation were attributed to the difference of adsorption and selectivity between the SPs and the two enantiomers through the adsorption experiments and the binding constants tests. Thus, both His-ZIF-93-bonded OT-CEC column and His/aImeIm@Zn-bonded OT-CEC column demonstrated the universality for the analytes, as well as excellent reproducibility, satisfactory stability and long lifetime.
研究领域:
分析化学
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材料科学
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DOI
PubMed
高影响因子
EUROPEAN FOOD RESEARCH AND TECHNOLOGY
·
2023
·Vol. 249
·期 4
·1137-1146
·
IF 3.3
Zhu Yan,Di Lei,Cheng Shengyu,Jin Yueying,Zhang Minghui,Zhang Lingli,Wang Xin,Li Xi-Ling,Han Yu,Xu Chun-Yan,Min Jun Zhe
A novel UHPLC–MS/MS method with high sensitivity and selectivity for simultaneous detection and chiral resolution of DL-amino acids in beer was established using the newly developed mass spectrometry probe (S)-(3-(4-carboxythiazolidin-3-yl)-3-oxopropyl) diphenylsulfonium (CTOD). The gradient analysis of five chiral amino acids (DL-Asp, DL-Glu, DL-Ala, DL-Pro, and DL-Phe) was carried out on a BEH C18 (2.1 × 150 mm, 1.7 μm) for 30 min with a mobile phase of 0.1% formic acid aqueous solution and 0.1% formic acid methanol/acetonitrile (7:3) solution. The resolutions of DL-amino acids ranged from 1.71 to 5.42. The correlation coefficients were ≥ 0.9994 in the range of 0.25 to 1200 pmol. Meanwhile, limits of detection (LOD) and limits of quantitative (LOQ) analysis were 0.05–0.25 pmol and 0.13–0.50 pmol, respectively. Furthermore, the intra-day and inter-day precision ranged from 0.34% to 6.31%, and the average recoveries ranged from 97.50% to 107.50%. The method was applied to the quantitative analysis and comparison of DL-amino acids in beer samples from 10 different manufacturers, and it was found that the beers were rich in D-amino acids. Four D-AAs including D-Ala, D-Pro, D-Glu, D-Phe (1.9–29.8 μmol L −1 ) and five L-AAs including L-Pro, L-Ala, L-Phe, L-Glu, L-Asp (5.3–2315.9 μmol L −1 ) were detected in the beer samples. The average content of L-AAs in the 10 beer samples was significantly higher than that of D-AAs. This study provides a new method for detecting chiral amino acids in beer and reliable data for evaluating the nutritional value of beer.
Graphical abstract
研究领域:
分析化学
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食品科学
·
营养学
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DOI
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
·
2024
·
IF 8.1
Zhiyong Ran,Tieyan Si,Xiankun Lin,Yue Li,Jie Han,Qiang He
Enantioselective separation plays a crucial role in pharmaceutical, agrochemical, and food industries. To improve the efficiency of enantioselective separation is still highly desirable and challenging. Here, an enantioseparation method was developed by employing magnetically-propelled microbots. The microbots were fabricated by sputter coating of the Ni layer onto the helical polyaniline (PANI) microfibers. Under a conical magnetic field, microbots exhibited the rotation-swing forward motion. Physical simulation showed that motion of the microbots leads to the forming of turbulence, showing micro-mixing effect and enhanced fluid diffusion. The microbots displayed higher separation efficiency and better stability for enantioselective separation of four kinds of racemic amino acids, compared to the PANI microfibers, with the enantiomeric excess (ee%) of 69.8 % for alanine. Magnetically-propelled motion of the microbots should increase the possibility of collision and recognition of amino acids with the PANI, enabling the improvement of the enantioseparation efficiency. This microbot-based methodology paves a promising way for highly efficient enantioselective separation.
研究领域:
材料科学
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生物医学工程
·
制药工程
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DOI
高影响因子
JOURNAL OF CHROMATOGRAPHY A
·
2013
·
IF 4.612
Mei Zhang,Jun-Hui Zhang,Yan Zhang,Bang-Jin Wang,Sheng-Ming Xie,Li-Ming Yuan
This study focused on exploring the chromatographic characteristic of a homochiral MOF [Cu 2 ( d -Cam) 2 (4,4′-bpy)] n with 3-D six-connected self-penetrating architectures for the separations of positional isomers and chiral compounds. Some effects such as mobile phase composition, column temperature, and analytes mass for separations on this chiral column also have been investigated. Among thirteen tested racemates, six compounds, namely three alcohols, a diol, a naphthol and a ketone were successfully discriminated, and ten useful positional isomers which have never been separated on other MOFs stationary phases in HPLC except dichlorobenzene and cresol isomers, were also analyzed by this chiral stationary phase. The results indicated that [Cu 2 ( d -Cam) 2 (4,4′-bpy)] n exhibited good selectivity for positional isomers and enantiomers. Therefore, it is practicable that the separation of positional isomers and enantiomers are carried out on the chiral MOF column.
研究领域:
分析化学
·
材料科学
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PubMed
高影响因子
Analytical Methods
·
2014
·Vol. 6
·期 12
·4408-4413
·
IF 1.938
Jiaqi Xie,Qi Tan,Lin Yang,Shenzhi Lai,Shaotan Tang,Changqun Cai,Xiaoming Chen
A simple, rapid and sensitive method for chiral separation of the amlodipine racemate was developed. (R)- and (S)-amlodipine enantiomers were separated by achiral HPLC, utilising dual chiral mobile phase additives, within 16 min, which was much faster than the previous similar studies. The method was established on an achiral WondaSil C18 column, using methanol–water (45 : 55 (v/v), pH 2.5) containing 7.5 mmol L−1 sulfobutylether-β-cyclodextrin (SBE-β-CD) and 0.3 mmol L−1 polyethylene glycol-20 000 (PEG-20M) as the mobile phase. Effects of additives and concentration, content of methanol and pH on the enantioseparation were investigated. The method was validated for linearity, repeatability, limits of detection (LOD) and limits of quantification (LOQ). The calibration curve (R(S)2 = 0.9998) was constructed in the range of 10–500 μg mL−1 for (S)-amlodipine. Repeatability (n = 6) showed less than 2% relative standard deviation (R.S.D.). LOD and LOQ were found to be 0.032 and 0.106 μg mL−1 for (S)-amlodipine. This method was flexible, simple and economically advantageous over the use of a chiral stationary phase, and was successfully applied to the determination of the amlodipine enantiomers in a commercial pharmaceutical tablets study.
研究领域:
药物分析
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分析化学
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DOI
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2017
·
IF 2.323
Panliang Zhang,Shichuan Wang,Weifeng Xu,Kewen Tang
Enantioselective liquid–liquid extraction (ELLE) was adopted to separate atenolol (AT) enantiomers, where tartrate and boric acid (BA) were used as the chiral selector. Influence of process variables on extraction efficiency were studied, including type of tartaric acid derivatives, type of the organic solvent, pH of aqueous phase, molality of BA and tartaric acid derivatives, as well as temperature. A theoretical model was developed based on the mechanism research on reactive extraction of AT enantiomers by n-hexyl (L)-tartrate (LT) and BA. Important parameters of this model were determined. By modeling and experiment, the optimal conditions identified involve the LT molality of 0.0796 mol·kg–1, BA molality of 0.1 mol·kg–1, AT molality of 1.592 mmol·kg–1, and pH value of 9.00 at 278 K, where the obtained enantioselectivity (α) is 1.8951 and performance factor (pf) is 0.0608.
研究领域:
化学工程
·
药物化学
·
分析化学
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DOI
高影响因子
ANALYTICAL CHEMISTRY
·
2023
·
IF 7.4
Bin Huang,Kuan Li,Qi-Yu Ma,Tuan-Xiu Xiang,Rui-Xue Liang,Ya-Nan Gong,Bang-Jin Wang,Jun-Hui Zhang,Sheng-Ming Xie,Li-Ming Yuan
Metallacycles are a novel class of supramolecular materials with circular structures, internal cavities, and abundant host–guest chemical properties that have exhibited good application prospects in many fields. However, to the best of our knowledge, no research on the use of metallacycles as stationary phases for gas chromatographic (GC) separations has been published yet. In this work, we report for the first time the use of a homochiral metallacycle, [ZnCl2L]2, as a stationary phase for GC separations. [ZnCl2L]2 was synthesized by reaction of (S)-(1-isonicotinoylpyrrolidin-2-yl)methyl-isonicotinate (L) with ZnCl2 via coordination-driven self-assembly. The [ZnCl2L]2-coated column displayed an excellent separation performance not only of organic isomers but also of racemic compounds. Sixteen racemates (including alcohols, esters, amino acid derivatives, ethers, organic acids, and epoxides) and 21 isomeric compounds (including positional, structural, and cis/trans-isomers) were well separated on the [ZnCl2L]2-coated column. Impressively, some racemates were resolved with high resolution values (Rs), including 1,2-butanediol diacetate (Rs = 25.86), ethyl 3-hydroxybutyrate (Rs = 20.97), 1,3-butanediol diacetate (Rs = 18.09), and threonine derivative (Rs = 18.61). Compared with the commercial β-DEX 120 column for separation of the tested racemates, the [ZnCl2L]2-coated column exhibited good enantioseparation complementarity, enabling separation of some racemates that could not be separated, or were not well resolved, by the β-DEX 120 column. In addition, many organic mixtures, such as n-alkanes, alkylbenzenes, n-alcohols, and a Grob test mixture, were also well separated on the [ZnCl2L]2-coated column. The column also has good reproducibility and thermal stability on separation. This work not only reveals the great potential of metallacycles for GC separations but also opens up a new application of metallacycles in separation science.
研究领域:
分析化学
·
材料科学
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DOI
PubMed
高影响因子
CHIRALITY
·
2024
·Vol. 36
·期 5
·e23674
·
IF 2.8
Xinwei Peng,Yongming Wei,Yangfeng Peng,Hongliang Zhao,Tianzhong Tong,Quan He
The separation of chiral drugs continues to pose a significant challenge. However, in recent years, the emergence of membrane-based chiral separation has shown promising effectiveness due to its environmentally friendly, energy-efficient, and cost-effective characteristics. In this study, we prepared chiral composite membrane via interfacial polymerization (IP), utilizing β-cyclodextrin (β-CD) and piperazine (PIP) as mixed monomers in the aqueous phase. The chiral separation process was facilitated by β-CD, serving as a chiral selective agent. The resulting membrane were characterized using SEM, FT-IR, and XPS. Subsequently, the chiral separation performance of the membrane for DL-tryptophan (Trp) was investigated. Lastly, the water flux, dye rejection, and stability of the membrane were also examined. The results showed that the optimized chiral PIP 0.5 β-CD 0.5 membrane achieved an enantiomeric excess percentage (ee%) of 43.0% for D-Trp, with a solute flux of 66.18 nmol·cm −2 ·h −1 , and maintained a good chiral separation stability. Additionally, the membrane demonstrated positive performance in the selective separation of mixed dyes, allowing for steady operation over a long period of time. This study offers fresh insights into membrane-based chiral separations.
研究领域:
生物化学
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材料科学
·
制药工程
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DOI
PubMed
高影响因子
REVIEWS IN ANALYTICAL CHEMISTRY
·
2024
·Vol. 43
·期 1
·
IF 3.6
Xiaoxi Si,Yu Tian,Shufang Xu,Chunbo Liu,Zhenjie Li,Ji Yang,Ying Guan,Yangzhou Xie,Xiaoqing Shi,Zhigang Xu,Zhihua Liu
Alkaloid enantiomers have different physiological and pharmacological effects, and different chiral compositions have a large impact on cigarette sensory and use safety. Studying the effects of different configurations of alkaloid enantiomers on cigarette sensory is important for the development of tobacco products, but the chiral separation of alkaloid enantiomers has become the core problem. Here, the application of a C18 column coupled with a polysaccharide-based chiral column to separate and detect four pairs of alkaloid enantiomers in tobacco and cigarette smoke of different brands was investigated. Results showed that the tandem technology of the two columns enabled the baseline separation of four pairs of alkaloid enantiomers. The resolution of enantiomers of alkaloids in different tobacco samples differed in content and ratio, showing different chiral distribution characteristics. According to the different distribution characteristics of alkaloid enantiomers, tobacco samples of different brands can be distinguished and real cigarettes can be identified.
研究领域:
分析化学
·
烟草科学
·
药物化学
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DOI
高影响因子
JOURNAL OF SEPARATION SCIENCE
·
2015
·Vol. 38
·期 11
·1813-1821
·
IF 2.737
Qiaoxuan Zhang,Jialiang Guo,Yuan Xiao,Jacques Crommen,Zhengjin Jiang
To further evaluate the feasibility and applicability of the one-pot strategy in monolithic column preparation, two novel β-cyclodextrin-functionalized organic polymeric monoliths were prepared using two β-cyclodextrin derivatives, i.e. mono(6-amino-6-deoxy)-β-cyclodextrin and heptakis(6-amino-6-deoxy)-β-cyclodextrin. In this improved method, mono(6-amino-6-deoxy)-β-cyclodextrin or heptakis(6-amino-6-deoxy)-β-cyclodextrin reacted with glycidyl methacrylate to generate the corresponding functional monomers and were subsequently copolymerized with ethylene dimethacrylate. The polymerization conditions for both monoliths were carefully optimized to obtain satisfactory column performance with respect to column efficiency, reproducibility, permeability, and stability. The obtained poly(glycidyl methacrylate-mono(6-amino-6-deoxy)-β-cyclodextrin- co -ethylene dimethacrylate) and poly(glycidyl methacrylate-heptakis(6-amino-6-deoxy)-β-cyclodextrin- co -ethylene dimethacrylate) monoliths exhibited a uniform structure, good permeability, and mechanical stability as indicated by scanning electron microscopy and micro-high-performance liquid chromatography experimental results. Because of the probable existence of multi-glycidyl methacrylate linking spacers on the poly(glycidyl methacrylate-heptakis(6-amino-6-deoxy)-β-cyclodextrin- co -ethylene dimethacrylate) monolith, the effect of the ratio of glycidyl methacrylate/heptakis(6-amino-6-deoxy)-β-cyclodextrin was especially studied, and satisfactory reproducibility could still be achieved by strictly controlling the composition of the polymerization mixture. To investigate the effect of the degree of amino substitution of β-cyclodextrin on column performance, a detailed comparison of the two monoliths was also carried out using series of analytes including small peptides and chiral acids. It was found that the β-cyclodextrin-functionalized monolith with mono-glycidyl methacrylate linking spacers demonstrated better chiral separation performance than that with multi-glycidyl methacrylate linking spacers.
研究领域:
分析化学
·
材料科学
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DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）