Chiral recognition in the solid state: crystallographically characterized diastereomeric co-crystals between a synthetic chiral selector (Whelk-O1) and a representative chiral analyte

Koscho, Michael E.; Spence, Patrick; Pirkle, William H.

doi:10.1016/j.tetasy.2005.08.027

Cited by 44 publications

(27 citation statements)

References 24 publications

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“…Examples include prediction of crystal structure by using co-crystals and two-dimensional laminated solids 20 and studying the separation mechanism of stationary phases. 21 Co-crystals can be prepared by a variety of techniques such as melt crystallization, grinding, 22 and recrystallization from solvents. 23 Like salts, cocrystals have the advantage that they can be screened for in a high-throughput platform.…”

Section: Introductionmentioning

confidence: 99%

The Co‐Crystal Approach to Improve the Exposure of a Water‐Insoluble Compound: AMG 517 Sorbic Acid Co‐Crystal Characterization and Pharmacokinetics

Bak

Gore

Yanez

et al. 2008

Journal of Pharmaceutical Sciences

205

195

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Section: Introductionmentioning

confidence: 99%

The Co‐Crystal Approach to Improve the Exposure of a Water‐Insoluble Compound: AMG 517 Sorbic Acid Co‐Crystal Characterization and Pharmacokinetics

Bak

Gore

Yanez

et al. 2008

Journal of Pharmaceutical Sciences

205

195

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“…41,42 Docking simulations were carried out considering only the structural features, which are understood to be essential for enantiomeric discrimination. 41,42 Docking simulations were carried out considering only the structural features, which are understood to be essential for enantiomeric discrimination.…”

Section: Computationalmentioning

confidence: 99%

Resolution, determination of enantiomeric purity and chiral recognition mechanism of new xanthone derivatives on (S,S)‐whelk‐O1 stationary phase

et al. 2017

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The enantioresolution and determination of the enantiomeric purity of 32 new xanthone derivatives, synthesized in enantiomerically pure form, were investigated on (S,S)-Whelk-O1 chiral stationary phase (CSP). Enantioselectivity and resolution (α and R ) with values ranging from 1.41-6.25 and from 1.29-17.20, respectively, were achieved. The elution was in polar organic mode with acetonitrile/methanol (50:50 v/v) as mobile phase and, generally, the (R)-enantiomer was the first to elute. The enantiomeric excess (ee) for all synthesized xanthone derivatives was higher than 99%. All the enantiomeric pairs were enantioseparated, even those without an aromatic moiety linked to the stereogenic center. Computational studies for molecular docking were carried out to perform a qualitative analysis of the enantioresolution and to explore the chiral recognition mechanisms. The in silico results were consistent with the chromatographic parameters and elution orders. The interactions between the CSP and the xanthone derivatives involved in the chromatographic enantioseparation were elucidated.

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“…Column Trade Name Supplier π-electron acceptor/π-electron donor phases and face-to-edge π-π-interactions to facilitate chiral recognition [144,145] ( Fig. 14.26b).…”

Section: Chiral Selectormentioning

confidence: 99%

Enantiomer Separations

2009

Introduction to Modern Liquid Chromatography

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Chiral recognition in the solid state: crystallographically characterized diastereomeric co-crystals between a synthetic chiral selector (Whelk-O1) and a representative chiral analyte

Cited by 44 publications

References 24 publications

The Co‐Crystal Approach to Improve the Exposure of a Water‐Insoluble Compound: AMG 517 Sorbic Acid Co‐Crystal Characterization and Pharmacokinetics

The Co‐Crystal Approach to Improve the Exposure of a Water‐Insoluble Compound: AMG 517 Sorbic Acid Co‐Crystal Characterization and Pharmacokinetics

Resolution, determination of enantiomeric purity and chiral recognition mechanism of new xanthone derivatives on (S,S)‐whelk‐O1 stationary phase

Enantiomer Separations

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