Three-column intermittent simulated moving bed chromatography: 2. Experimental implementation for the separation of Tröger's Base

Jermann, Simon; Alberti, Andreas S. Leon; Mazzotti, Marco

doi:10.1016/j.chroma.2014.08.057

Cited by 11 publications

(16 citation statements)

References 14 publications

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“…Chiral compounds, especially chiral drugs, have identical physical and chemical properties but very often exhibit different biological, pharmacological, toxicological activities, and metabolism pathways in living system. Diverse analytical techniques have been developed for separating chiral compounds including various chromatography, CE , membrane separation, crystallization, metal organic framework, and chemical recognition . However, most techniques require time‐consuming procedures, high cost, quite large consumption of solvents, as well as complicated pre‐treatment steps for samples.…”

Section: Methodsmentioning

confidence: 99%

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Kim

Lee

2016

Bulletin Korean Chem Soc

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Chirality is a universal and important phenomenon in nature. It refers to the property of a molecule or system which is not identical to its mirror image. In chemical field, chirality is used to describe the lack of a symmetric plane in molecules. Chiral compounds, especially chiral drugs, have identical physical and chemical properties but very often exhibit different biological, pharmacological, toxicological activities, and metabolism pathways in living system. Diverse analytical techniques have been developed for separating chiral compounds including various chromatography, 1-5 CE, 6 membrane separation, 7,8 crystallization 9 , metal organic framework, 10 and chemical recognition. 11 However, most techniques require time-consuming procedures, high cost, quite large consumption of solvents, as well as complicated pre-treatment steps for samples. Thus, it leads to an increasing demand for developing simple and efficient methods for chiral separation.Cyclodextrin and their derivatives, such as carboxymethylβ-cyclodextrin (CMCD), which consist of a hydrophobic internal cavity and a hydrophilic outer surface have been used widely as a chiral selector because of their excellent chiral recognition capabilities. [12][13][14] In this study, we report the synthesis of carboxymethyl-β-cyclodextrin modified zirconiapoly(amidoamine) (PAMAM) dendrimer-magnetic microspheres (CMCD-ZPMMs) that was carried out via repetitive Michael addition reactions by using microwave irradiation. The product was tried to apply in selective enantioseparation of racemic drugs using polarimetric technique. To the best of our knowledge, the direct separation of racemic drugs by using CMCD-ZPMMs has not been reported yet.The scheme of the preparation for CMCD-ZPMMs is displayed in Scheme 1. Firstly, magnetic microspheres, Fe 3 O 4 were synthesized via solvothermal reaction, and then coated with glucose by hydrothermal reaction before coating with zirconia. The surface of Zirconia magnetic microspheres was modified with (3-aminopropyl) triethoxysilane (APTES) to form primary amine groups. The morphologies of obtained products were investigated in our previous report. 15 Subsequently, to make more bonding sites for efficient conjugation with chiral selector, PAMAM dendrimers were grown onto ZPMMs by repeating the Michael addition and amidation reaction by using ultrasonic system. The synthetic procedures for preparing CMCD-ZPMMs are presented in Supporting information (Appendix S1).Initial assessments of CMCD-ZPMMs for separating chiral drugs were performed using ketopropen, propranolol, and acebutolol. Sample solutions containing these three drugs showed no optical activity because they are comprised of equal amounts of the (+) and (−) enantiomers, called a racemic mixture. It is well-known that the sign (+/−) of the rotation change depends on the nature and macroscopic behavior of the compound, such as the substituents attached to the stereocenter, the number of molecules in the path of the light. The scheme of the separation of racemic drugs vi...

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Section: Methodsmentioning

confidence: 99%

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Kim

Lee

2016

Bulletin Korean Chem Soc

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“…Schematic process setup for the 4-zone simulated moving bed (SMB) and the reduced 3-zone SMB (acc. to [30][31][32]).…”

Section: Tlc Screeningmentioning

confidence: 99%

Systematic and Model-Assisted Process Design for the Extraction and Purification of Artemisinin from Artemisia annua L.—Part III: Chromatographic Purification

et al. 2018

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In this study, the purification of an extract from Artemisia annua L. using chromatographic methods is studied. In a first step, a screening of different phases and solvents using thin-layer chromatography (TLC) was performed. Then, a laboratory-scale high performance liquid chromatography (HPLC) method was developed and transferred to a pilot scale. A reproducibility study based on 120 injections was carried out. The batch process that was developed and the results from a designed continuous simulated moving bed (SMB) chromatography were compared based on characteristic process numbers and economy.

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“…However, large safety margins are needed due to the band broadening effects. The 3C‐ISMB had up to an 82 % increase in productivity over that of the four‐zone I‐SMB when applied to the separation of Tröger's base enantiomers .…”

Section: Operating Strategies To Extend the Potential Of Conventionalmentioning

confidence: 99%

Advanced Operating Strategies to Extend the Applications of Simulated Moving Bed Chromatography

et al. 2017

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Chromatographic separation with solid stationary and fluid mobile phases is widely used to isolate and purify compounds. One of the most productive improvements in preparative chromatography is the simulated moving bed (SMB) process, which enables continuous feed supply and product removal by periodic operation of a multicolumn to simulate a countercurrent flow between the phases. The SMB process produces high‐purity compounds, even with low selectivity, and offers higher productivity and lower eluent consumption than batch chromatography. Recently, intensive efforts have been made to expand the range of applications through the design, modeling, and optimization of the SMB process to produce advanced operating strategies, which are described and evaluated in this review.

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Three-column intermittent simulated moving bed chromatography: 2. Experimental implementation for the separation of Tröger's Base

Cited by 11 publications

References 14 publications

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Systematic and Model-Assisted Process Design for the Extraction and Purification of Artemisinin from Artemisia annua L.—Part III: Chromatographic Purification

Advanced Operating Strategies to Extend the Applications of Simulated Moving Bed Chromatography

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