HPLC enantioseparation on a homochiral MOF–silica composite as a novel chiral stationary phase

RSC Advances ◽  
2016 ◽  
Vol 6 (26) ◽  
pp. 21293-21301 ◽  
Author(s):  
Koichi Tanaka ◽  
Toshihide Muraoka ◽  
Yasuhiro Otubo ◽  
Hiroki Takahashi ◽  
Atsushi Ohnishi
Keyword(s):  
Stationary Phase ◽  
Dicarboxylic Acid ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Starting Material ◽  
Silica Composite

Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for HPLC to separate the enantiomers.

Enantioseparation of Cinacalcet, and its Two Related Compounds by HPLC with Self-Made Chiral Stationary Phases and Chiral Mobile Phase Additives

2019 ◽  
Vol 15 (2) ◽  
pp. 200-209
Author(s):  
Canyu Yang ◽  
Ji Li ◽  
Yanyun Yao ◽  
Chen Qing ◽  
Baochun Shen
Keyword(s):  
Stationary Phase ◽  
Mobile Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Starting Material ◽  
Mobile Phase Additives ◽  
Chiral Mobile Phase Additives ◽  
Related Compounds

Background: Cinacalcet is one of the second-generation calcimimetics which consists of a chiral center. The pharmacological effect of R-cinacalcet is 1000 times greater than that of the Scinacalcet. As mentioned in many literatures, 1-(1-naphthyl)ethylamine is used as the starting material for the synthesis of cinacalcet. The absolute structure of cinacalcet is influenced by the starting materials. Methods: We present the chiral separation of cinacalcet and its starting material, 1-(1-naphthyl) ethylamine along with one of its intermediates, N-(1-(naphthalen-1-yl) ethyl)-3- (3-(trifluoromethyl) phenyl) propanamide by high-performance liquid chromatography with chiral stationary phase and chiral mobile phase additives. Results: On vancomycin and cellulose tri 3,5-dimethylphenylcarbamate) chiral stationary phase, cinacalcet and 1-(1-naphthyl)ethylamine achieved enantioseparation under normal phase with addition of triethylamine additives, respectively. Meanwhile, 1-(1-naphthyl)ethylamine and N-(1-(naphthalen-1- yl)ethyl)-3-(3-(trifluoromethyl) phenyl) propanamide achieved enantioseparation on 1-napthalene vancomycin chiral stationary phase using D-tartaric acid, diethyl L-tartrate and diethyl D-tartrate as chiral mobile phase additives. Conclusion: The chiral recognition in our experiment was based on the hydrogen-bonding, dipoledipole and π-π interactions among the solutes, chiral stationary phases and chiral mobile phase additives. In addition, the space adaptability of chiral stationary phases also affected the separation efficacy.

Chiral stationary phases consisting of π-conjugated polymers bearing glucose-linked biphenyl units: reversible switching of resolution abilities based on a coil-to-helix transition

2017 ◽  
Vol 8 (29) ◽  
pp. 4190-4198 ◽  
Author(s):  
Tomoyuki Ikai ◽  
Seiya Awata ◽  
Tomoya Kudo ◽  
Ryoma Ishidate ◽  
Katsuhiro Maeda ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Conjugated Polymers ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases

We have succeeded in developing a novel chiral stationary phase that can reversibly switch resolution abilities based on a coil-to-helix transition in a column.

scholarly journals Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5477
Author(s):  
Carla Fernandes ◽  
Joana Teixeira ◽  
Madalena M. M. Pinto ◽  
Maria Elizabeth Tiritan
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Separation And Purification ◽  
Enantioselective Chromatography ◽  
Synthetic Approaches ◽  
Applied Coating ◽  
Selection Of

Enantioselective chromatography is one of the most used techniques for the separation and purification of enantiomers. The most important issue for a specific successful enantioseparation is the selection of the suitable chiral stationary phase (CSP). Different synthetic approaches have been applied for the preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced recently. In this review, an overview of different methods for the preparation of coated and immobilized CSPs is described. Updated examples of CSPs associated with the various strategies are presented. Considering that after the preparation of a CSP its characterization is fundamental, the methods used for the characterization of all the described CSPs are emphasized.

Chiral separation and a molecular modeling study of eight azole antifungals on the cellulose tris(3,5-dichlorophenylcarbamate) chiral stationary phase

2018 ◽  
Vol 42 (16) ◽  
pp. 13421-13429 ◽  
Author(s):  
Bolin Zhu ◽  
Fan Zhao ◽  
Jia Yu ◽  
Zhaokun Wang ◽  
Yongbo Song ◽  
...  
Keyword(s):  
Liquid Chromatography ◽  
Molecular Modeling ◽  
Stationary Phase ◽  
Chiral Separation ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Normal Phase ◽  
Azole Antifungals ◽  
Phase Liquid

Four immobilized polysaccharide-based chiral stationary phases have been examined for their enantioselectivity on azole analytes using normal phase liquid chromatography.

scholarly journals HIGH – PERFORMANCE LIQUID CHROMATOGRAPHIC METHOD FOR ENANTIOSEPARATION OF UNDERIVATIZED α-AMINO ACIDS USING CYCLOFRUCTAN – BASED CHIRAL STATIONARY PHASES

2013 ◽  
Vol 12 (2) ◽  
pp. 108-119 ◽  
Author(s):  
Jakub Moravčík ◽  
Katarína Hroboňová
Keyword(s):  
Amino Acids ◽  
Stationary Phase ◽  
Mobile Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
High Performance Liquid Chromatographic ◽  
Optical Isomers ◽  
Chiral Amino Acids

Abstract Chromatographic columns with chiral stationary phases based on chemically - bonded derivatized cyclofructans were evaluated for HPLC enantioresolution of underivatized α-amino acids. The analytical study of chiral separation of these analytes was focused on the selection of suitable chiral stationary phase and mobile phase. Using isopropyl carbamate cyclofructan 6 as a chiral stationary phase, α- amino acid optical isomers were separated. The retention and enantioseparation of chiral amino acids were also influenced by a mobile phase composition. The mixture methanol/acetonitrile/acetic acid/triethylamine (75/25/0.3/0.2 v/v/v/v) was found to be the most effective mobile phase for HPLC separation of studied compounds. HPLC enantioresolution of chiral amino acids was thermodynamically studied. Based on the enthalpy and entropy contribution values calculated from the van´t Hoff equation, HPLC enantioseparation under chosen chromatographic conditions was found to be an enthalpically driven.

Determination of methionine enantiomers by HPLC on the cyclofructan chiral stationary phase

2015 ◽  
Vol 7 (11) ◽  
pp. 4577-4582 ◽  
Author(s):  
Katarína Hroboňová ◽  
Jakub Moravčík ◽  
Jozef Lehotay ◽  
Daniel W. Armstrong
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
Stationary Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Enantiomeric Separation

The enantiomeric separation of methionine by high performance liquid chromatography on various cyclofructan type chiral stationary phases in the polar-organic separation mode was studied.

scholarly journals Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: Enantioseparation of NSAIDs

2017 ◽  
Vol 36 (1-2) ◽  
pp. 130-148 ◽  
Author(s):  
Nurul Yani Rahim ◽  
Kheng Soo Tay ◽  
Sharifah Mohamad
Keyword(s):  
Ionic Liquid ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Spectroscopic Studies ◽  
Inclusion Complex Formation ◽  
H Nmr ◽  
Inflammatory Drugs ◽  
And Performance ◽  
Multiple Interactions

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.

Stationary phase-related investigations of quinine-based zwitterionic chiral stationary phases operated in anion-, cation-, and zwitterion-exchange modes

2009 ◽  
Vol 1216 (7) ◽  
pp. 1147-1156 ◽  
Author(s):  
Christian V. Hoffmann ◽  
Roland Reischl ◽  
Norbert M. Maier ◽  
Michael Lämmerhofer ◽  
Wolfgang Lindner
Keyword(s):  
Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases

Preparation of (R)-(-)-6,6'-Bis(3,5-dinitrobenzamido)biphenyl-2,2'-dicarboxylic Acid, a Potential Chiral HPLC Selector

1995 ◽  
Vol 60 (12) ◽  
pp. 2161-2164 ◽  
Author(s):  
Miloš Tichý ◽  
Jiří Závada
Keyword(s):  
Stationary Phase ◽  
Dicarboxylic Acid ◽  
Chiral Stationary Phase ◽  
Optically Active ◽  
Chiral Hplc ◽  
Hplc Separation ◽  
Separation Of Enantiomers

The title optically active diacid I has been prepared as a potential selector for chiral stationary phase in the HPLC separation of enantiomers.

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