Techniques in Preparative Chiral Separations

Franco, Pilar; Minguillón, Cristina

doi:10.1002/3527600361.ch1

Cited by 10 publications

(12 citation statements)

References 111 publications

(139 reference statements)

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“…The resolution of enantiomers can be achieved by various methods, [2] including fractional crystallization, microbiological methods, kinetic enzymatic resolution, and chromatography. Of growing importance are methods that permit the continuous production of pure enantiomers, such as by liquid-solid partitioning in simulated moving bed (SMB) chromatography, [3] chiral-membranebased separation techniques, [4] and polymers imprinted with chiral templates. [5] Although all these techniques show high chiral discrimination, they are not yet applicable for the large-scale resolution of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Crystallization on Chiral Polymeric Microspheres

Medina¹,

Goldshtein²,

Margel³

et al. 2007

Adv Funct Materials

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In this article, a new approach to chiral resolution based on enantioselective crystallization on chiral polymeric microspheres is presented. To demonstrate the approach, a new synthetic method is developed for the preparation of porous and hollow chiral polymeric microspheres. Chiral microspheres based on poly(N‐vinyl α‐L‐phenylalanine) (PV‐L‐Phe) are synthesized from uniform polystyrene (PS) microsphere templates by a single‐step swelling process. The chiral microspheres display a narrow size distribution, and their properties, especially the porosity, can be controlled by varying the synthesis conditions. The chiral discrimination ability of these chiral microspheres is studied for DL‐valine crystallization, as a model system for chiral racemic crystallization. X‐ray diffraction (XRD) and differential scanning calorimetry (DSC) provide evidence for the crystallization of enantiopure crystals on the chiral polymeric microspheres. Optical rotation measurements during crystallization show an enatiomeric excess of ca. 25 % for L‐valine in the chiral microspheres. Although this excess is not yet very high, the basic principle of chiral discrimination by enantioselective crystallization on chiral microspheres is demonstrated.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Crystallization on Chiral Polymeric Microspheres

Medina¹,

Goldshtein²,

Margel³

et al. 2007

Adv Funct Materials

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“…Vor kurzem erschienen umfassende Übersichten, [35][36][37][38][39] und es stehen hervorragende Beschreibungen ausgewählter Verfahrenskonzepte zur Verfügung (z. B. Lit.…”

Section: Verfahren Zur Enantiomerentrennungunclassified

“…[35,36]. Vorgestellt werden beispielsweise die enantioselektive Schaumflotation, präparative Gelelektrophorese und Destillation.…”

Section: Andere Trenntechnikenunclassified

“…[31,36,38,[192][193][194][195][196][197][198][199][200][201][202] Analog zum Gebiet der Kristallisation hat man auch in der Chromatographie große Anstrengungen unternommen, um derivatisierende Reagentien zur Erzeugung von Diastereomeren einzusetzen, die dann durch klassische chromatographische Verfahren getrennt werden kçnnen. Da diese "indirekte" Methode einige Nachteile aufweist, wie beispielsweise unterschiedliche Umwandlungsgeschwindigkeiten der beiden Enantiomere oder das Risiko einer Racemisierung, [200] Je nach Eigenschaften des zu trennenden Gemischs werden Gase, Flüssigkeiten oder überkritische Flüssigkeiten als mobile Phase eingesetzt.…”

Section: Chromatographische Enantiomerentrennungunclassified

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Verfahren zur Enantiomerentrennung

Lorenz

Seidel‐Morgenstern

2014

Angewandte Chemie

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Die Verfügbarkeit reiner Enantiomere ist von steigender Bedeutung für die pharmazeutische Industrie sowie auch für die Agrochemie und Biotechnologie. Generell gibt es zwei konkurrierende Ansätze zur Gewinnung von reinen Enantiomeren. Der “chirale” Ansatz basiert auf der Entwicklung einer asymmetrischen Synthese, die selektiv eines der Enantiomere liefert. Der “racemische” Ansatz basiert auf der Trennung eines Gemischs der beiden Enantiomere, wobei hier in den letzten Jahren bemerkenswerte Fortschritte erzielt werden konnten. Dieser Aufsatz fokussiert insbesondere auf enantioselektive Kristallisationsprozesse und präparative Chromatographie, einschließlich hybrider Trennprozesse und der zusätzlichen Integration von Racemisierungsschritten. Zur Illustration dienen mehrere in unserem Arbeitskreis untersuchte Trennungen.

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“…HPLC using chiral stationary phases (CSP) is one of the most convenient and flexible techniques for enantioseparation [1,2]. It is widely used to perform separations of small, analytical, sample sizes.…”

Section: Introductionmentioning

confidence: 99%

Chromatographic enantioseparation of amino acids using a new chiral stationary phase based on a macrocyclic glycopeptide antibiotic

Petrusevska

Кузнецов

Gedicke

et al. 2006

J of Separation Science

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The separation of the enantiomers of several a-amino acids was studied on a new chiral stationary phase (CSP) which is based on the macrocyclic glycopeptide antibiotic eremomycin attached to silica particles. Retention and separation factors were determined under analytical conditions at ambient temperature for different mobile phase compositions. In order to evaluate the potential with respect to preparative separations the adsorption isotherms of D- and L-methionine were determined for one mobile phase composition applying the elution by characteristic point method. The isotherms were validated by comparing experimentally determined elution profiles with predictions based on the equilibrium dispersive model. Finally, the performance of the eremomycin CSP was compared with a commercially available CSP based on the macrocyclic antibiotic teicoplanin. After determining the isotherms of D- and L-methionine also for the teicoplanin phase, the equilibrium dispersive model was used for both CSP to identify optimal operating conditions. For the separation and conditions considered the new eremomycin CSP revealed a better performance compared to the teicoplanin CSP.

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Techniques in Preparative Chiral Separations

Cited by 10 publications

References 111 publications

Enantioselective Crystallization on Chiral Polymeric Microspheres

Enantioselective Crystallization on Chiral Polymeric Microspheres

Verfahren zur Enantiomerentrennung

Chromatographic enantioseparation of amino acids using a new chiral stationary phase based on a macrocyclic glycopeptide antibiotic

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