Chiral Stationary Phases for Preparative Enantioselective Chromatography

Francotte, Eric

doi:10.1002/9780470988428.ch3

Cited by 19 publications

(24 citation statements)

References 124 publications

(159 reference statements)

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“…[37,200,219,220] Die Fixierung einer chiralen Selektorspezies am chromatographischen Träger (meist porçse Kieselgelpartikel) erfolgt entweder durch kovalente Bindung oder durch starke physikalische Adsorption (z. B. durch Beschichtung mit einem polymeren Selektor).…”

Section: Chirale Stationäre Phasenunclassified

“…[8,223,224] Es gibt verschiedene Klassifizierungen für CSPs. [200,220,225] Die nachfolgende Übersicht orientiert sich an der Gliederung der wichtigsten Selektoren für die CSP an Lit. [200].…”

Section: Chirale Stationäre Phasenunclassified

“…Die wichtige Problematik der Beladbarkeiten und Sättigungska-pazitäten der CSPs wird in Lit. [219,220] angesprochen. Die Identifizierung des am besten geeigneten chromatographischen Systems zur Lçsung eines spezifischen Trennproblems mithilfe systematischen Säulenscreenings wurde vor kurzem erläutert, [243] ebenso wie Versuche zur Miniaturisierung zur Ermçglichung von Hochdurchsatzmethoden.…”

Section: Synthetische Ionische Moleküle Mit Geringem Molekulargewichtunclassified

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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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Section: Chirale Stationäre Phasenunclassified

Section: Synthetische Ionische Moleküle Mit Geringem Molekulargewichtunclassified

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Verfahren zur Enantiomerentrennung

Lorenz

Seidel‐Morgenstern

2014

Angewandte Chemie

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“…While efforts to develop improved covalently immobilized analogs of Chiralpak AD have been carried out by Chiral Technologies and others, 1,5,6 the fact remains that Chiralpak AD is still, at the time of this writing, the CSP of choice for carrying out preparative separations. We were therefore interested in learning more about what eluents and conditions give rise to polymer stripping, and initiated a study in this area.…”

Section: Introductionmentioning

confidence: 98%

Investigation of the stability of Chiralpak AD chiral stationary phase under various solvent conditions and development of a method to identify stationary phase‐derived polymer contamination

2006

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The stability of Chiralpak AD chiral stationary phase under various solvent conditions was investigated. An analytical method for the detection of the presence of solubilized Chiralpak AD coating was developed using CD spectroscopy (CD signal at 245 nm). In addition, NMR analysis of the solubilized polymer revealed a characteristic signal for the 3,5-dimethylphenyl carbamate methyl protons at around 2.5 ppm. Both of these methods may be helpful in detecting contamination by the Chiralpak AD polymer or in the study of CSP solvent compatibility.

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“…Separating enantiomers on liquid chromatographic chiral stationary phases (CSPs) has been known to be quite effective as an analytical method for the determination of the enantiomeric composition of chiral compounds and as a preparative method for the separation of enantiomers [1][2][3][4][5]. During the last several decades, quite effective CSPs have been developed by utilizing various chiral selectors.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition

Agneeswari

Sung

et al. 2016

Molecules

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Abstract:Two new diastereomeric chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral tethering group and a Π-basic chiral unit such as (R)-1-(1-naphthyl) ethylamine (CSP 1) or (S)-1-(1-naphthyl)ethylamine (CSP 2) were prepared. The two CSPs were applied to the enantiomeric separation of N-(3,5-dinitrobenzoyl)-1-phenylalkylamines and N-(3,5-dinitrobenzoyl)-α-amino acid derivatives using 20% isopropyl alcohol in hexane as a normal mobile phase. To elucidate the effect of the two chiral units on the chiral recognition, the chiral recognition abilities of the two CSPs were compared with each other and with that of a CSP (CSP 3) based on (R)-1-(1-naphthyl)ethylamine. From the chromatographic chiral recognition results, (R)-1-(1-naphthyl)ethylamine and (+)−(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 1 were concluded to show a cooperative ("matched") effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative ("mismatched") effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs.

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Chiral Stationary Phases for Preparative Enantioselective Chromatography

Cited by 19 publications

References 124 publications

Verfahren zur Enantiomerentrennung

Verfahren zur Enantiomerentrennung

Investigation of the stability of Chiralpak AD chiral stationary phase under various solvent conditions and development of a method to identify stationary phase‐derived polymer contamination

Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition

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