Cyclodextrin Derivatives in GC Separation of Racemic Mixtures of Volatiles. Part XIV: Some Applications of Thick-Film Wide-Bore Columns to Enantiomer GC Micropreparation

Bicchi, Carlo; Balbo, Cristina; D’Amato, Angela; Manzin, Valeria; Schreier, Peter; Rozenblum, A. B.; Brunerie, Pascal

doi:10.1002/(sici)1521-4168(19980201)21:2<103::aid-jhrc103>3.0.co;2-q

Cited by 15 publications

(3 citation statements)

References 10 publications

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“…Micropreparative enantioseparations by GC on modified cyclodextrins have been achieved on thick-film wide-bore fused-silica capillary columns [233]. The enantiomers of 2 mg of racemic methyl jasmonate were enantioseparated within 80 min on a 1.8 m × 4mm i.d.…”

Section: Preparative-scale Gas Chromatographic Enantioseparationmentioning

confidence: 99%

Separation of Enantiomers by Gas Chromatography on Chiral Stationary Phases

Schurig

2010

Chiral Separation Methods for Pharmaceutical and Biotechnological Products

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Section: Preparative-scale Gas Chromatographic Enantioseparationmentioning

confidence: 99%

Separation of Enantiomers by Gas Chromatography on Chiral Stationary Phases

Schurig

2010

Chiral Separation Methods for Pharmaceutical and Biotechnological Products

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“…An interesting example of the use of such cyclodextrin-based artificial enzymes is asymmetric and stereospecific synthesis (halogenation, hydrohalogenation, oxidation, reduction, photolysis, aldol reactions, hydrogenation, substitution and addition reaction) [25]. Noteworthy, the stereoselectivity of CDs was utilized for separation of racemic mixtures [27,28].…”

Section: Introductionmentioning

confidence: 99%

Predicting Value of Binding Constants of Organic Ligands to Beta-Cyclodextrin: Application of MARSplines and Descriptors Encoded in SMILES String

Cysewski

Przybyłek

2019

Symmetry

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The quantitative structure–activity relationship (QSPR) model was formulated to quantify values of the binding constant (lnK) of a series of ligands to beta–cyclodextrin (β-CD). For this purpose, the multivariate adaptive regression splines (MARSplines) methodology was adopted with molecular descriptors derived from the simplified molecular input line entry specification (SMILES) strings. This approach allows discovery of regression equations consisting of new non-linear components (basis functions) being combinations of molecular descriptors. The model was subjected to the standard internal and external validation procedures, which indicated its high predictive power. The appearance of polarity-related descriptors, such as XlogP, confirms the hydrophobic nature of the cyclodextrin cavity. The model can be used for predicting the affinity of new ligands to β-CD. However, a non-standard application was also proposed for classification into Biopharmaceutical Classification System (BCS) drug types. It was found that a single parameter, which is the estimated value of lnK, is sufficient to distinguish highly permeable drugs (BCS class I and II) from low permeable ones (BCS class II and IV). In general, it was found that drugs of the former group exhibit higher affinity to β-CD then the latter group (class III and IV).

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“…Nevertheless, the diffusion of this approach was limited because of the low α value of the chiral selectors used as stationary phases (usually in the range 1.02-1.20) in most of the cases avoiding collection of enantiomeric pure components [43]. Different approaches were exploited in micropreparative separation of enantiomers using wide-bore columns coated with cyclodextrin stationary phases (CSPs) by Bicchi et al [44,45].…”

Section: Introductionmentioning

confidence: 99%