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Journal articles on the topic 'Enantioseparation'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 March 2023

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1

Zhao, Yuan, Xuecheng Zhu, Wei Jiang, Huilin Liu, and Baoguo Sun. "Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects." Molecules 26, no. 4 (February 21, 2021): 1145. http://dx.doi.org/10.3390/molecules26041145.

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With the rapid development of global industry and increasingly frequent product circulation, the separation and detection of chiral drugs/pesticides are becoming increasingly important. The chiral nature of substances can result in harm to the human body, and the selective endocrine-disrupting effect of drug enantiomers is caused by differential enantiospecific binding to receptors. This review is devoted to the specific recognition and resolution of chiral molecules by chromatography and membrane-based enantioseparation techniques. Chromatographic enantiomer separations with chiral stationary phase (CSP)-based columns and membrane-based enantiomer filtration are detailed. In addition, the unique properties of these chiral resolution methods have been summarized for practical applications in the chemistry, environment, biology, medicine, and food industries. We further discussed the recognition mechanism in analytical enantioseparations and analyzed recent developments and future prospects of chromatographic and membrane-based enantioseparations.

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2

Čižmáriková, R., A. Némethy, J. Valentová, K. Hroboňová, and K. Bruchatá. "Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone." Acta Facultatis Pharmaceuticae Universitatis Comenianae 59, no. 2 (December 28, 2012): 15–27. http://dx.doi.org/10.2478/v10219-012-0023-7.

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AbstractWithin the framework of the study of the synthesis and high-performance liquid chromatography (HPLC) enantioseparation the series of 9 derivatives of 3-hydroxyphenylethanone was prepared by a well-tried method. The structure of the prepared compounds was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of prepared compounds was performed using HPLC on a native teicoplanin (Chirobiotic T) and the amylose tris (3,5-dimethylphenylcarbamate) (Chiralpak AD) chiral stationary phases, which is more suitable for the enantioseparation of all prepared compounds especially with heterocycles in the basic part of a molecule.

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3

Zhang, Qiongwen, Junyuan Zhang, Xia Wang, Jia Yu, and Xingjie Guo. "Enantioseparation of Eight Pairs of Tetralone Derivative Enantiomers on Cellulose Based Chiral Stationary Phase by HPLC." Current Pharmaceutical Analysis 16, no. 5 (June 15, 2020): 539–47. http://dx.doi.org/10.2174/1573412915666181130111103.

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Background: Tetralone derivatives, important resources for the development of new drugs which can act in the treatment of central nervous system disorders or participate in synthesis reaction for the synthesis of various pharmaceuticals, have great research value and a bright prospect in exploitation. Methods: A novel chiral HPLC method for efficient enantioseparation of eight tetralone derivative enantiomers was developed on cellulose based CHIRALPAK IC chiral stationary phase under normal mode by investigating the effects of type and content of organic modifier, column temperature and flow rate on retention and enantioselectivity. Besides, the specificity, linearity, stability, precision, accuracy and robustness of this method were also validated. Results: Satisfactory enantioseparation was obtained for all enantiomers in n-hexane/2-propanol mobile phase system at ambient temperature. The thermodynamic study indicated that the solute transfer from the mobile to stationary phase was enthalpically favorable, and the process of enantioseparation was mainly enthalpy controlled. This method met the requirements for quantitative determination of tetralone derivative enantiomers. Conclusion: This study can provide great and important application value for enantioseparation of eight pairs of newly synthesized tetralone derivative enantiomers under normal mode using CHIRALPAK IC chiral column.

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4

Čižmáriková, R., S. Chudáčiková, J. Valentová, and A. Némethy. "Synthesis and enantioseparation of derivatives of propranolol." Acta Facultatis Pharmaceuticae Universitatis Comenianae 59, no. 1 (January 1, 2012): 5–13. http://dx.doi.org/10.2478/v10219-012-0012-x.

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Synthesis and enantioseparation of derivatives of propranololPropranolol is one of the first prepared and in therapeutic praxis used beta- adrenolytics. In this paper novel derivatives of propranolol with cyclohexylamino and pyrrolidin-1-yl groups in hydrophilic part were prepared. HPLC-enantioseparation propranolol (as reference compound) and of the prepared derivatives has been achieved using a Chiralpak AD CSP based on the amylose tris (3,5-dimethylphenylcarbamate).(R)-enantiomer of the propranolol was prepared by stereoselective synthesis using Jacobsen catalyst.

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5

Chen, Ming, Xinling Lu, Xiaofei Ma, Yin Xiao, and Yong Wang. "Click preparation of multiple-thioether bridged cyclodextrin chiral materials for efficient enantioseparation in high-performance liquid chromatography." Analyst 146, no. 9 (2021): 3025–33. http://dx.doi.org/10.1039/d1an00145k.

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6

YASHIMA, EIJI, and YOSHIO OKAMOTO. "Chiral Membranes for Enantioseparation." Sen'i Gakkaishi 51, no. 4 (1995): P150—P155. http://dx.doi.org/10.2115/fiber.51.4_p150.

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7

Eichhorn, Ralf. "Enantioseparation in microfluidic channels." Chemical Physics 375, no. 2-3 (October 2010): 568–77. http://dx.doi.org/10.1016/j.chemphys.2010.06.021.

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8

Gössi, Angelo, Wolfgang Riedl, and Boelo Schuur. "Enantioseparation with liquid membranes." Journal of Chemical Technology & Biotechnology 93, no. 3 (October 19, 2017): 629–44. http://dx.doi.org/10.1002/jctb.5417.

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9

Lao, Wenjian. "Thermodynamic and Extrathermodynamic Studies of Enantioseparation of Imidazolinone Herbicides on Chiralcel OJ Column." ISRN Chromatography 2013 (May 16, 2013): 1–9. http://dx.doi.org/10.1155/2013/460787.

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A homologous series of chiral imidazolinone herbicide was previously resolved on Chiralcel OJ column in high performance liquid chromatography. However, the mechanism of the chiral separation remains unclear. In this study, chromatographic behaviors of five chiral imidazolinone herbicides were characterized by thermodynamic and extrathermodynamic methods in order to enhance the understanding of the chiral separation. Thermodynamic parameters of this study were derived from equilibrium constant () that was estimated from the moment analysis of the chromatographic peak. Van't Hoff plots of ( versus ) were linear at a range of 15–50°C, only nonlinear at a range of 5–15 °C with n-hexane (0.1%, trifluoroacetic acid)-2-propanol 60/40 (v/v) mobile phase. The enantiomer retention on the chiral column was entropy-driven at a lower temperature (5°C) and enthalpy-driven at a higher temperature (10 to 50°C). Enantioseparations of four of the five imidazolinone herbicides were enthalpy-driven, only entropy-driven for imazaquin. Enantioseparation mechanisms were different in between 5–10°C and 15–50°C probably due to the conformational change of the OJ phase. Enthalpy-entropy compensation showed similar mechanisms in retention and chiral separation for the five or enantiomers. Several extrathermodynamic relationships were able to be extracted to address additivity of group contribution.

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10

Peluso, Paola, Alessandro Dessì, Roberto Dallocchio, Barbara Sechi, Carlo Gatti, Bezhan Chankvetadze, Victor Mamane, et al. "Enantioseparation of 5,5′-Dibromo-2,2′-dichloro-3-selanyl-4,4′-bipyridines on Polysaccharide-Based Chiral Stationary Phases: Exploring Chalcogen Bonds in Liquid-Phase Chromatography." Molecules 26, no. 1 (January 4, 2021): 221. http://dx.doi.org/10.3390/molecules26010221.

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The chalcogen bond (ChB) is a noncovalent interaction based on electrophilic features of regions of electron charge density depletion (σ-holes) located on bound atoms of group VI. The σ-holes of sulfur and heavy chalcogen atoms (Se, Te) (donors) can interact through their positive electrostatic potential (V) with nucleophilic partners such as lone pairs, π-clouds, and anions (acceptors). In the last few years, promising applications of ChBs in catalysis, crystal engineering, molecular biology, and supramolecular chemistry have been reported. Recently, we explored the high-performance liquid chromatography (HPLC) enantioseparation of fluorinated 3-arylthio-4,4′-bipyridines containing sulfur atoms as ChB donors. Following this study, herein we describe the comparative enantioseparation of three 5,5′-dibromo-2,2′-dichloro-3-selanyl-4,4′-bipyridines on polysaccharide-based chiral stationary phases (CSPs) aiming to understand function and potentialities of selenium σ-holes in the enantiodiscrimination process. The impact of the chalcogen substituent on enantioseparation was explored by using sulfur and non-chalcogen derivatives as reference substances for comparison. Our investigation also focused on the function of the perfluorinated aromatic ring as a π-hole donor recognition site. Thermodynamic quantities associated with the enantioseparation were derived from van’t Hoff plots and local electron charge density of specific molecular regions of the interacting partners were inspected in terms of calculated V. On this basis, by correlating theoretical data and experimental results, the participation of ChBs and π-hole bonds in the enantiodiscrimination process was reasonably confirmed.

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11

Li, Linwei, Chengjun Wu, Yang Ma, Shuhao Zhou, Zhen Li, and Tiemin Sun. "Effectively enhancing the enantioseparation ability of β-cyclodextrin derivatives by de novo design and molecular modeling." Analyst 142, no. 19 (2017): 3699–706. http://dx.doi.org/10.1039/c7an00986k.

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12

Zhou, Zhiyong, Ke Cui, Yu Mao, Wenshuai Chai, Nian Wang, and Zhongqi Ren. "Green preparation of d-tryptophan imprinted self-supported membrane for ultrahigh enantioseparation of racemic tryptophan." RSC Advances 6, no. 111 (2016): 109992–10000. http://dx.doi.org/10.1039/c6ra23555g.

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13

Jurin, Mladenka, Darko Kontrec, Tonko Dražić, and Marin Roje. "Enantioseparation of syn- and anti-3,5-Disubstituted Hydantoins by HPLC and SFC on Immobilized Polysaccharides-Based Chiral Stationary Phases." Separations 9, no. 7 (June 22, 2022): 157. http://dx.doi.org/10.3390/separations9070157.

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The enantioseparation of syn- and anti-3,5-disubstituted hydantoins 5a–i was investigated on three immobilized polysaccharide-based columns (CHIRAL ART Amylose-SA, CHIRAL ART Cellulose-SB, CHIRAL ART Cellulose-SC) by high performance liquid chromatography (HPLC) using n-hexane/2-PrOH (90/10, v/v) or 100% dimethyl carbonate (DMC) as mobile phases, respectively, and by supercritical fluid chromatography (SFC) using CO2/alcohol (MeOH, EtOH, 2-PrOH; 80/20, v/v) as a mobile phase. The chromatographic parameters, such as separation and resolution factors, have indicated that Amylose-SA is more suitable for enantioseparation of the most analyzed syn- and anti-3,5-disubstituted hydantoins than Celullose-SB and Cellulose-SC in both HPLC and SFC modalities. All three tested columns showed better enantiorecognition ability toward anti-hydantoins compared to syn-hydantoins, both in HPLC and SFC modes. We have demonstrated that environmentally friendly solvent DMC can be efficiently used as the mobile phase in HPLC mode for enantioseparation of hydantoins on the immobilized polysaccharide-based chiral stationary phases.

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14

Rahim, Nurul Yani, Kheng Soo Tay, and Sharifah Mohamad. "Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs." Adsorption Science & Technology 36, no. 1-2 (January 25, 2017): 130–48. http://dx.doi.org/10.1177/0263617416686798.

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Recently, we reported a new chiral stationary phase prepared using β-cyclodextrin functionalized with aromatic ionic liquid which is aimed to enhance the performance of enantioseparation of flavonoids and β-blockers. In this paper, the characteristics and performance of previously prepared chiral stationary phase denoted as β-CD-BIMOTs were compared with the newly synthesized chiral stationary phase denoted as β-CD-DIMOTs. β-CD-DIMOTs were prepared by functionalization of β-cyclodextrin with aliphatic ionic liquid. The obtained β-CD-BIMOTs and β-CD-DIMOTs stationary phases were compared with native β-CD stationary phase for the enantioseparation of non-steroidal anti-inflammatory drugs (NSAIDs) (ibuprofen, indoprofen, ketoprofen and fenoprofen). The β-CD-BIMOTs stationary phase showed greater chiral resolution capabilities rather than β-CD-DIMOTs and native β-CD stationary phases. Further, in order to understand the interaction of enantioseparation, the inclusion complex formation between NSAIDs and β-CD-BIMOTs was studied using 1H NMR, NOESY and UV/Vis. The enantioseparated NSAIDs were found to form multiple interactions with β-CD-BIMOTs-CSP.

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15

Guo, Siyu, Chao Huang, Ning Zhang, Shujuan Ma, Chunmiao Bo, Bolin Gong, and Junjie Ou. "Enantioseparation in high performance liquid chromatography: preparation and evaluation of a vancomycin-based chiral stationary phase via surface-initiated atom transfer radical polymerization." Analytical Methods 14, no. 12 (2022): 1221–31. http://dx.doi.org/10.1039/d2ay00108j.

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16

Zhang, Juan, Xiao-Chen Wang, Wei Chen, and Zheng-Wu Bai. "Synthesis of substituted phenylcarbamates of N-cyclobutylformylated chitosan and their application as chiral selectors in enantioseparation." Analyst 141, no. 14 (2016): 4470–80. http://dx.doi.org/10.1039/c6an00311g.

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17

Zhang, Shaopeng, Huanhuan Wang, Jian Tang, Wei Wang, and Weihua Tang. "Exploration of a β-cyclodextrin clicked chiral stationary phase in high-performance liquid chromatography." Anal. Methods 6, no. 7 (2014): 2034–37. http://dx.doi.org/10.1039/c3ay42193g.

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18

Berkecz, Róbert, Gábor Németi, Antal Péter, and István Ilisz. "Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans." Molecules 26, no. 15 (July 31, 2021): 4648. http://dx.doi.org/10.3390/molecules26154648.

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Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

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19

ABE, Yoshiohiro, Tomoko SHOJI, Shikie FUKUI, Maki SASAMOTO, and Hideyuki NISHIZAWA. "Enantioseparation by Dual-flow Countercurrent Extraction: Its Application to the Enantioseparation of (.+-.)-Propranolol." CHEMICAL & PHARMACEUTICAL BULLETIN 44, no. 8 (1996): 1521–24. http://dx.doi.org/10.1248/cpb.44.1521.

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20

Zhang, Juan, Zhao-Qun Wang, Xiao-Chen Wang, Jun-Jun Zhang, Zheng-Wu Bai, and Wei Chen. "Enantioseparation characteristics of tadalafil and its intermediate on chitin derived chiral stationary phases." Analyst 140, no. 16 (2015): 5593–600. http://dx.doi.org/10.1039/c5an00260e.

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21

Hu, Xiao-Jing, Ge Huang, Shuo Zhang, Zhi-Bin Fang, Tian-Fu Liu, and Rong Cao. "An easy and low-cost method of embedding chiral molecules in metal–organic frameworks for enantioseparation." Chemical Communications 56, no. 54 (2020): 7459–62. http://dx.doi.org/10.1039/d0cc03349a.

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22

Chang, Limin, Jinming Zhang, Weiwei Chen, Mei Zhang, Chunchun Yin, Weiguo Tian, Zhu Luo, Weili Liu, Jiasong He, and Jun Zhang. "Controllable synthesis of cellulose benzoates for understanding of chiral recognition mechanism and fabrication of highly efficient chiral stationary phases." Analytical Methods 10, no. 24 (2018): 2844–53. http://dx.doi.org/10.1039/c8ay00162f.

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23

Zhou, Yanli, Chunhong Zhang, Rui Ma, Lijia Liu, Hongxing Dong, Toshifumi Satoh, and Yoshio Okamoto. "Synthesis of helical poly(phenylacetylene) derivatives bearing diastereomeric pendants for enantioseparation by HPLC." New Journal of Chemistry 43, no. 8 (2019): 3439–46. http://dx.doi.org/10.1039/c8nj05579c.

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24

Ružena, Čižmáriková, Habala Ladislav, Valentová Jindra, and Šmátralová Dana. "Syntéza a HPLC enantioseparácia nových derivátov 3-alkoxy-4-hydroxyfenylalkanónov typu potenciálnych α/β-blokátorov." Česká a slovenská farmacie 70, no. 1 (2021): 51–58. http://dx.doi.org/10.5817/csf2021-2-51.

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The present paper reports the synthesis of a series of seven compounds with a hetero aminopropanol chain. The compounds were prepared by the conversion of 3-alkoxy-4-hydroxyphenyl alkanones with 2-chloromethyl oxirane and subsequent reaction of the products with heterocyclic amines (pyrrolidine, azepane, 4-methylpiperazine and 2-methoxyphenyl piperazine). The target compounds were synthesized in the form of racemates. The purity of the products was confirmed by thin layer chromatography and their IR, UV-VIS and 1H-NMR spectra were recorded. Enantioseparation of the racemic products was accomplished by HPLC on a Chiralpak AD chiral chromatographic column with tris(3,5-dimethylphenyl)carbamate as the chiral selector. The efficiency of enantioseparation was determined in relation to the composition of the mobile phase (hexane : ethanol : methanol : ethylethanamine) and to the structure of the prepared compounds. Baseline separation was achieved with all compounds using mobile phases A (78 : 11 : 11 : 0,1 v/v/v/v) and B (80 : 10 : 10 : 0,1 v/v/v/v), with selectivity factor ranging from 1.07 to 1.42 and resolution from 0.76 to 5.47. The mobile phase containing a higher amount of hexane did not allow for successful enantioseparation of the piperazine derivatives.

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25

Tanaka, Koichi, Naoki Hotta, Shohei Nagase, and Kenji Yoza. "Efficient HPLC enantiomer separation using a pillared homochiral metal–organic framework as a novel chiral stationary phase." New Journal of Chemistry 40, no. 6 (2016): 4891–94. http://dx.doi.org/10.1039/c6nj00090h.

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26

Shi, Ge, Xiao Dai, Yue Zhou, Jie Zhang, Jun Shen, and Xinhua Wan. "Synthesis and enantioseparation of proline-derived helical polyacetylenes as chiral stationary phases for HPLC." Polymer Chemistry 11, no. 18 (2020): 3179–87. http://dx.doi.org/10.1039/d0py00205d.

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27

Lee, Kun Won, Ahmed H. E. Hassan, Youngdo Jeong, Seolmin Yoon, Seung-Hwan Kim, Cheol Jung Lee, Hye Rim Jeon, et al. "Enantiopure methoxetamine stereoisomers: chiral resolution, conformational analysis, UV-circular dichroism spectroscopy and electronic circular dichroism." New Journal of Chemistry 45, no. 9 (2021): 4354–64. http://dx.doi.org/10.1039/d0nj05192f.

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28

Yu, Hai-Rong, Li Lei, Yan-Lin Wang, Xi Wang, Ting Liang, and Chang-Jing Cheng. "A chiral magnetic molybdenum disulfide nanocomposite for direct enantioseparation of RS-propranolol." RSC Advances 13, no. 8 (2023): 5249–58. http://dx.doi.org/10.1039/d2ra04866c.

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29

Popovic, A., T. McBriar, P. He, and A. Beavis. "Chiral determination and assay of optical isomers in clandestine drug laboratory samples using LC-MSMS." Analytical Methods 9, no. 22 (2017): 3380–87. http://dx.doi.org/10.1039/c6ay03125k.

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30

Wu, Jingwei, Ping Su, Danhua Guo, Jun Huang, and Yi Yang. "Cationic β-cyclodextrin-modified hybrid magnetic microspheres as chiral selectors for selective chiral absorption of dansyl amino acids." New J. Chem. 38, no. 8 (2014): 3630–36. http://dx.doi.org/10.1039/c4nj00030g.

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31

Baranowska, Irena, Judyta Hejniak, and Sylwia Magiera. "LC-ESI-MS/MS method for the enantioseparation of six flavanones." Analytical Methods 9, no. 6 (2017): 1018–30. http://dx.doi.org/10.1039/c6ay02952c.

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32

Soleymani, Elham, Heshmatollah Alinezhad, Masoud Darvish Ganji, and Mahmood Tajbakhsh. "Enantioseparation performance of CNTs as chiral selectors for the separation of ibuprofen isomers: a dispersion corrected DFT study." Journal of Materials Chemistry B 5, no. 33 (2017): 6920–29. http://dx.doi.org/10.1039/c7tb00755h.

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33

Allenmark, S. G., and John D. Green. "Chromatographic enantioseparation — methods and applications." Analytica Chimica Acta 223 (1989): 472. http://dx.doi.org/10.1016/s0003-2670(00)84115-x.

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34

Zhang, Chunhong, Lijia Liu, and Yoshio Okamoto. "Enantioseparation using helical polyacetylene derivatives." TrAC Trends in Analytical Chemistry 123 (February 2020): 115762. http://dx.doi.org/10.1016/j.trac.2019.115762.

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35

Cannazza, Giuseppe, Daniela Braghiroli, Marina M. Carrozzo, Carlo Parenti, Cesare Sabbioni, Roberto Mandrioli, Salvatore Fanali, and Maria Augusta Raggi. "Enantioseparation of the antidepressant reboxetine." Journal of Pharmaceutical and Biomedical Analysis 48, no. 3 (November 2008): 991–96. http://dx.doi.org/10.1016/j.jpba.2008.06.026.

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36

Pietruszka, Jo¨rg, Detlev H. Hochmuth, Ba¨rbel Gehrcke, Detlef Icheln, Torsten Runge, and Wilfried A. Ko¨nig. "Gas chromatographic enantioseparation of allenes." Tetrahedron: Asymmetry 3, no. 5 (May 1992): 661–70. http://dx.doi.org/10.1016/s0957-4166(00)82299-5.

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37

Winkler, Margit, and Norbert Klempier. "Enantioseparation of nonproteinogenic amino acids." Analytical and Bioanalytical Chemistry 393, no. 6-7 (January 11, 2009): 1789–96. http://dx.doi.org/10.1007/s00216-008-2564-0.

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38

Chaloner, Penny A. "Chromatographic enantioseparation; methods and applications." Journal of Organometallic Chemistry 375, no. 2 (October 1989): C58—C60. http://dx.doi.org/10.1016/0022-328x(89)85126-5.

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39

Ryoo, Jae Jeong, Kyu Sung Heo, Eun-Soon Choi, Jung Hag Park, and Wonjae Lee. "Enantioseparation of tiropramide by HPLC." Chirality 16, S1 (2004): S51—S54. http://dx.doi.org/10.1002/chir.20050.

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40

Franchini, Silvia, Annamaria Baraldi, Claudia Sorbi, Federica Pellati, Elena Cichero, Umberto M. Battisti, Piero Angeli, Antonio Cilia, and Livio Brasili. "Enantiomeric resolution of [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl](2-phenoxyethyl)amine, a potent α1and 5-HT1Areceptor ligand: an in vitro and computational study." Med. Chem. Commun. 6, no. 4 (2015): 677–90. http://dx.doi.org/10.1039/c4md00484a.

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41

Zhou, Yanli, Chunhong Zhang, Zhengjin Zhou, Ruiqi Zhu, Lijia Liu, Jianwei Bai, Hongxing Dong, Toshifumi Satoh, and Yoshio Okamoto. "Influence of different sequences of l-proline dipeptide derivatives in the pendants on the helix of poly(phenylacetylene)s and their enantioseparation properties." Polymer Chemistry 10, no. 35 (2019): 4810–17. http://dx.doi.org/10.1039/c9py00675c.

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42

Malik, Poonam, and Ravi Bhushan. "Synthesis of diastereomeric anhydrides of (RS)-ketorolac and (RS)-etodolac, semi-preparative HPLC enantioseparation, establishment of molecular asymmetry and recovery of pure enantiomers." New Journal of Chemistry 41, no. 22 (2017): 13681–91. http://dx.doi.org/10.1039/c7nj02898a.

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43

Tang, Haitong, Keke Yang, Kun-Yu Wang, Qi Meng, Fan Wu, Yu fang, Xiang Wu, et al. "Engineering a homochiral metal–organic framework based on an amino acid for enantioselective separation." Chemical Communications 56, no. 63 (2020): 9016–19. http://dx.doi.org/10.1039/d0cc00897d.

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44

Hroboňová, Katarína, Jozef Lehotay, and Jozef Čižmárik. "HPLC Enantioseparation of Phenylcarbamic Acid Derivatives by Using Macrocyclic Chiral Stationary Phases." Nova Biotechnologica et Chimica 15, no. 1 (June 1, 2016): 12–22. http://dx.doi.org/10.1515/nbec-2016-0002.

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Abstract The HPLC by using chiral stationary phases based on macrocyclic antibiotics, dimethylphenyl carbamate cyklofructan 7 and β-cyclodextrin in terms of polar-organic separation mode (mobile phase methanol/acetonitrile/acetic acid/triethylamine) were used for enantioseparation of alkoxy derivatives of phenylcarbamic acid. The effect of the analyte structures on the efficiency of enantioseparation was investigated. The most suitable stationary phase was teicoplanin aglycone, where the separations of the enantiomers were obtained (the resolution value from 0.65 to 2.90, depending on the structure of the analyte). Significant effect on the resolution of the enantiomers has position of alkoxy substituent in the hydrophobic part of the molecule. The enantiorecognition was achieved for 3-alkoxysubstituted derivatives.

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CHEN, XIAO-QING, XIAO-YUN LIAO, JIN-GANG YU, FEI-PENG JIAO, and XIN-YU JIANG. "CHIRAL CARBON NANOTUBES AND CARBON NANOTUBE CHIRAL COMPOSITES: PREPARATION AND APPLICATIONS." Nano 08, no. 04 (July 17, 2013): 1330002. http://dx.doi.org/10.1142/s1793292013300028.

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A review of preparation of chiral carbon nanotubes (CNTs) and carbon nanotube chiral composites is presented. Novel chiral separation science and technology based on CNTs is analyzed and discussed, with the emphasis in two topics. The first topic concerns the possibility of application of chiral CNTs in resolution and chiral sensing. The second topic centers on the subject of enantioseparation based on CNT chiral composites. Despite the crucial functionalization of CNTs using chiral selectors, better resolution could also be achieved by using a mixture of CNTs and optical pure substances as chiral selectors. Due to their ability of improving the degree of enantioseparation, CNTs could find their potential applications in the resolution in the future.

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46

Yoshida, Hiroto, Masahiro Ehara, U. Deva Priyakumar, Tsuyoshi Kawai, and Takuya Nakashima. "Enantioseparation and chiral induction in Ag29 nanoclusters with intrinsic chirality." Chemical Science 11, no. 9 (2020): 2394–400. http://dx.doi.org/10.1039/c9sc05299b.

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Buljan, Anđela, and Marin Roje. "Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides." Marine Drugs 20, no. 8 (August 19, 2022): 530. http://dx.doi.org/10.3390/md20080530.

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Enantioseparation of the newly synthesized series of novel quinoline-2(1H)-one epoxide structures rac-6a–c and rac-8a–c, named marinoepoxides, is described. Marinoepoxide rac-6a, the key intermediate in the total synthesis of natural products marinoaziridines A and B, as well as their structural analogues, was synthesized by addition of the achiral ylide generated in situ from the sulfonium salt 5 or 7, to the carbon-oxygen double bond of the corresponding quinoline-2(1H)-one-4-carbaldehyde 4a–c in good yield. Separation of enantiomers of (±)-2,3,3-trisubstituted marinoepoxides rac-6a–c and (±)-trans-2,3-disubstituted marinoepoxides rac-8a–c was studied using two immobilized polysaccharide type chiral stationary phases (CSPs); tris-(3,5-dichlorophenylcarbamoyl)cellulose stationary phase (CHIRAL ART Cellulose-SC) and tris-(3,5-dimethylphenylcarbamoyl)amylose stationary phase (CHIRAL ART Amylose-SA). Enantioseparation conditions were explored by high-performance liquid chromatography (HPLC) using dimethyl carbonate/alcohol mixtures and n-hexane/ethanol (80/20, v/v) as mobile phase, and by supercritical fluid chromatography (SFC) using CO2/alcohol mixtures as mobile phase. In all examined racemates, enantioseparation was successfully achieved, but its efficiency largely depended on the structure of chiral selector and type/composition of the mobile phase.

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Lv, Lili, Lijuan Wang, Yanan Zou, Rui Chen, and Jiaojiao Yu. "Chiral separation by nonaqueous capillary electrophoresis using l-sorbose–boric acid complexes as chiral ion-pair selectors." RSC Advances 6, no. 106 (2016): 104193–200. http://dx.doi.org/10.1039/c6ra21806g.

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Kodama, Koichi, Fusato Takase, and Takuji Hirose. "Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents." RSC Advances 11, no. 30 (2021): 18162–70. http://dx.doi.org/10.1039/d1ra03546k.

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Enantioseparation of atropisomeric biphenols using a chiral amidine derived from dehydroabietic acid was reported. Only one crystallization of their mixture gave pure diastereomeric salts of biphenols from racemate.

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Ma, Xiaofei, Jingtang Li, Xiaoqi Li, Zijie Feng, Xuan Yang, Jie Liu, and Yingxiang Du. "L-Histidinium Chiral Ionic Liquid Functionalized β-Cyclodextrin as Chiral Selector in Capillary Electrophoresis." Journal of Chromatographic Science 59, no. 4 (January 22, 2021): 388–95. http://dx.doi.org/10.1093/chromsci/bmaa115.

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Abstract Nowadays, ionic liquids (ILs) functionalized cyclodextrins (CDs) have drawn increasing attention in chiral separation. Herein, a novel β-CD derivative functionalized by L-histidinium IL, mono-6-deoxy-6-L-histidinium-β-cyclodextrin chloride (L-HMCDCl), was synthesized for the first time and utilized for enantioseparation of nefopam and chlorphenamine in capillary electrophoresis. The L-HMCDCl exhibited superior enantioselectivity compared with native β-CD. The effect of some key parameters such as chiral selector concentration, buffer pH and applied voltage on the enantioseparation was investigated in detail. In the interest of the chiral discrimination mechanism and the enhanced enantioselectivity of L-HMCDCl, molecular modeling with AutoDock was employed to study the interaction, which was in good agreement with experimental results.

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