JOURNAL OF CHROMATOGRAPHY A
·
2019
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IF 3.858
Xiaofei Ma,Yingxiang Du,Xiaodong Sun,Jie Liu,Zhifeng Huang
In this study, three functionalized chiral ionic liquids (CILs) derived from l -valinol, l -prolinol and l -phenylalaninol, namely N,N,N- trimethyl- l -valinol-bis(trifluoromethanesulfon)imide ([TMLV] + [Tf 2 N] − , CIL1), N,N- dimethyl- l -prolinol-bis(trifluoromethanesulfon)imide ([DMLP] + [Tf 2 N] − , CIL2) and N,N,N- trimethyl- l -phenylalaninol-bis(trifluoromethanesulfon)imide ([TMLP] + [Tf 2 N] − , CIL3), were synthesized and subsequently utilized for enantiomeric separation in capillary electrophoresis (CE) with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) as chiral selector for the first time. Compared with traditional single HP-β-CD separation system, the synergistic system exhibited substantially improved separations of six tested drugs. Using the CIL1/HP-β-CD as a model system, the influence of crucial parameters including the type and proportion of organic modifier, CILs concentration, HP-β-CD concentration and buffer pH was investigated in detail. Additionally, molecular modeling with AutoDock was applied to elucidate the enhanced enantioselectivity in the presence of CILs, which has certain guiding value in predicting the migration order of the enantiomers and studying the interactions important for the chiral recognition.
研究领域:
分析化学
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药物化学
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产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2024
·Vol. 25
·期 11
·5606
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IF 4.9
Rong Wang,Kaiyue Song,Zhaoqin Wei,Yue Sun,Xiaoxia Sun,Yu Hu
The chiral H8-BINOL derivatives R-1and R-2were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1highly enantioselective towards it.
研究领域:
超分子化学
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有机化学
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分析化学
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DOI
PubMed
高影响因子
Analytical Methods
·
2016
·Vol. 8
·期 5
·1127-1134
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IF 1.915
Ning An,Lijuan Wang,Jingjing Zhao,Lili Lv,Ning Wang,Huaizhong Guo
An interesting study on chiral nonaqueous capillary electrophoresis (NACE) was developed in this paper. Two new chiral selectors, a lactobionic acid–boric acid complex and a D-(+)-xylose–boric acid complex were respectively in situ synthesized in nonaqueous background electrolytes (BGEs) containing methanol and triethylamine. They were found to be applicable for the enantioseparation of fourteen amino alcohols including eight β-blockers and six β-agonists by NACE. In order to achieve good enantioseparation, the effects of chiral selector concentration, BGE composition, capillary temperature, and applied voltage were systematically investigated. Under the optimized conditions, most of the tested amino alcohols achieved good chiral resolution. The effects of the molecular structures of chiral selectors and analytes on enantioseparation were discussed in terms of molecular interactions. The method was proved to be suitable for routine analysis of propranolol enantiomers, since it provided satisfactory results during linearity, precision, and accuracy (recovery) studies using the lactobionic acid–boric acid complex as the chiral selector. Good linearity was obtained in the range of 1.0–100.0 μg mL−1 for each propranolol enantiomer and the recoveries for them ranged from 96.4% to 105.9% with the relative standard deviation (RSD) less than 6.4%. This chiral NACE method was applied for the determination of propranolol enantiomers from tablets and the average contents were 101.3% for (R)-propranolol and 98.5% for (S)-propranolol (n = 5).
研究领域:
分析化学
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药物分析
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手性分离
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电泳技术
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药物代谢
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分子识别
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药剂学
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DOI
高影响因子
CARBOHYDRATE POLYMERS
·
2025
·
IF 12.5
Qian Jiang,Lijia Liu,Xuan Yuan,Huan Li,Yudan Wang,Junqing Li
To address the ecological pollution caused by synthetic antimicrobial agents in conventional food packaging films, we have successfully developed a fully bio-based and sustainable food packaging film that exhibits exceptional antibacterial and antioxidant properties. In this study, we designed and synthesized two novel natural alcohol esters of amino acid (NAEAAs)—L-Trp-Men and L-Trp-Bor—through esterification reactions involving L -tryptophan ( L -Trp) and L -Menthol or Borneol, respectively. A multifunctional composite film system was constructed using natural corn starch (CS) and sodium carboxymethyl cellulose (CMC) as the matrix materials, with NAEAAs serving as the antimicrobial active components and curcumin (Cur) as the antioxidant. Experimental results demonstrated that the CS/CMC/Men2/Cur2 composite film, containing 2 wt% additives, exhibited nearly complete (≈100 %) broad-spectrum antibacterial efficiency against both Escherichia coli and Staphylococcus aureus , alongside a DPPH radical scavenging rate of 45.69 ± 1.39 %. Cytotoxicity tests confirmed the excellent biocompatibility of NAEAAs, which hydrolyze into amino acids and natural alcohols, thereby minimizing environmental contamination. These fully natural material-based films present a novel approach for developing green, pollution-free, and renewable bio-based food packaging materials.
研究领域:
食品科学
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高分子科学
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材料工程
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生物技术
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环境科学
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化学合成
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）