Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers

Francotte, Eric

doi:10.1016/s0021-9673(00)00951-1

Cited by 531 publications

(335 citation statements)

References 94 publications

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“…Several chiral phases are available for preparative separation, among others cellulose derivative-based phases (CTA I, Chiralcel OD, OJ, OB, Chiralpack AD, AS, Daicel), a polymeric phase (Chiraspher, Merck), crosslinked l-diallyltartramide derivatives (Kromasil CHI-DMB, CHI-TTB) and a Pirkle type phase (DNBPG). A recent review [264] summarizes the applications of preparative LC. One technique, which allows separation of enantiomers at a 100 g scale is the batch chromatographic mode [265].…”

Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Chiral Imprinted Polymersmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

223

135

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“…In recent years, much effort has been expended on researching methods of fabricating nanoscale chiral surfaces, in many cases with the goal of improving enantioselectivity in asymmetric induction 6 , high-performance liquid chromatography 7,8 and high-sensitivity chirality detection 9,10 . Fabrication techniques include cleaving metal surfaces along low-symmetry planes 11 , adsorption of chiral molecules onto metal surfaces [12][13][14] , electrodeposition 15 , molecular imprinting [16][17][18] , glancing-angle deposition 19 and employment of metal-organic frameworks 20 .…”

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confidence: 99%

Diastereomeric liquid crystal domains at the mesoscale

et al. 2015

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In many technologies used to achieve separation of enantiomers, chiral selectors are designed to display differential affinity for the two enantiomers of a chiral compound. Such complexes are diastereomeric, differing in structure and free energy for the two enantiomers and enabling chiral discrimination. Here we present evidence for strong diastereomeric interaction effects at the mesoscale, manifested in chiral liquid crystal guest materials confined in a chiral, nanoporous network of semi-crystalline helical nanofilaments. The nanoporous host is itself an assembly of achiral, bent-core liquid crystal molecules that phase-separate into a conglomerate of 100 micron-scale, helical nanofilament domains that differ in structure only in the handedness of their homogeneous chirality. With the inclusion of a homochiral guest liquid crystal, these enantiomeric domains become diastereomeric, exhibiting unexpected and markedly different mesoscale structures and orientation transitions producing optical effects in which chirality has a dominant role.

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“…This stationary phase was developed primarily by the Okamoto group (Okamoto and Kaida, 1990;Okamoto and Kaida, 1994;Okamoto and Ikai, 2008) and has been successfully used to separate several chiral molecules (Silva Jr. et al, 2012;Francotte, 1994;Francotte, 2001;Lourenço et al, 2012). The chemical structure of the chiral selector is depicted in Figure 2.…”

Section: Figure 1: Chemical Structures Of Verapamil Enantiomers: (A) mentioning

confidence: 99%

Chromatographic Separation of Verapamil Racemate Using a Varicol Continuous Multicolumn Process

Cremasco

Santana²

2015

Braz. J. Chem. Eng.

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-Verapamil is a chiral drug that is marketed in its racemic form, but because of the pharmacological effects due to molecule's chirality, one of the enantiomers is more potent, and the other exhibits different activities of therapeutic interest. The preparative separation of the verapamil enantiomers was performed using a continuous Varicol unit operated on a scale of 1 g/day. Amylose tris(3,5-dimethylphenylcarbamate) functioned as the stationary phase, and n-hexane/isopropanol/ethanol mixtures were used as the mobile phase. Diethylamine was used as the additive. The enantiomeric purities were 93.0% for S-(-)-verapamil and 92.0% for R-(+)-verapamil in the raffinate and extract streams, respectively. The unit provided productivities of 0.18 kg of raffinate per day per kg of adsorbent and 0.20 kg of extract per day per kg of adsorbent when using a feed concentration of 12.5 g L -1 .

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Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers

Cited by 531 publications

References 94 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Diastereomeric liquid crystal domains at the mesoscale

Chromatographic Separation of Verapamil Racemate Using a Varicol Continuous Multicolumn Process

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