High-performance liquid chromatographic separation of dihydropyrimidine racemates on polysaccharide-derived chiral stationary phases

Nadalini, Giorgio; Dondi, Francesco; Massi, Alessandro; Dondoni, Alessandro; Zhang, Tong; Cavazzini, Alberto

doi:10.1016/j.chroma.2006.05.095

Cited by 8 publications

(6 citation statements)

References 22 publications

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“…16 DHPMs are generally resolved poorer on polysaccharide-derived CSPs than on the brush-type CSPs reported here and earlier. 11 This refers to the coated as well as to immobilized polysaccharide-derived CSPs.…”

Section: Resultscontrasting

confidence: 62%

“…The separation factors achieved for the enantiomers of this compound are 1.61, 1.56, and 1.50, respectively, considerably more than 1.20 obtained on polysaccharide CSPs. 16 Monastrol is currently a leading cell permeable compound for the development of new anticancer drugs. 18,19 Given this biological activity, usable quantities of the enantiomers of Monastrol constitute a target of importance.…”

Section: Resultsmentioning

confidence: 99%

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Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

2007

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The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. By combining all of these CSPs, the enantiomers of all DHPM derivatives used in this study can be properly resolved. Particularly good enantioresolutions were achieved for thioureide derivatives, such as Monastrol. The results presented show that sulfur-aromatic interactions are meritorious for these very good separations.

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Section: Resultscontrasting

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

2007

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“…Based on authors' experience, − MP modifier amounts used in almost all practical NP mode separations are large enough to assume the completion of adsorption surface monolayers. These findings are consistent with theories or semiempirical models, employed to describe retention in NP chromatography, in which surface monolayer coverage is implicitly assumed.…”

Section: Resultsmentioning

confidence: 99%

Adsorption Mechanisms in Normal-Phase Chromatography. Mobile-Phase Modifier Adsorption from Dilute Solutions and Displacement Effect

et al. 2007

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The adsorption equilibria of methanol from diluted solutions of the alcohol in dichloromethane (the weak solvent of the binary mixture) have been investigated in normal-phase conditions on an hybrid polymeric chiral stationary phase. This was done by analyzing the shapes of nonlinear perturbations of methanol, measured with a refractive index detector from a column in equilibrium with pure dichloromethane. Experiments have been set up to demonstrate the displacement effect, predictable from the adsorption data, by a nonlinear pulse of methanol on a racemic mixture of temazepam injected at trace level. A most used method in fundamental studies of band behavior in chromatography has been used for modeling the system. An extraordinary increase of the apparent column efficiency has been observed due to the displacement phenomenon, with the peak of the second eluted enantiomer noticeably higher and narrower than that of the first eluted component.

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“…In a previous work (Schmid et al ., 2006), our group presented the possibility of applying the chiral separation principle of ligand‐exchange on dynamically coated monolithic columns using long‐chain N ‐alkyl‐derivatives of l ‐4‐hydroxyproline as chiral selectors. Several other authors described the successful application of dynamically coated phases in HPLC using different types of chiral selectors either immobilized on a monolithic support or on conventionally packed columns (Remelli et al ., 1997; Haroun et al ., 2006; Nadalini et al ., 2006; Natalini et al ., 2006, 2008; Guillaume and Andre, 2008; Wang et al ., 2008; Yamamoto et al ., 2008; Zaher et al ., 2008).…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative

Pittler

Schmid

2010

Biomedical Chromatography

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In this work a chiral stationary phase was prepared by dynamically coating a monolithic reversed-phase HPLC column with a vancomycin-derivative as chiral selector. A hydrophobic alkyl-chain was attached to the vancomycin molecule, providing the immobilization of the chiral selector on the reversed-phase material. Dansyl amino acids were chosen as model analytes for testing the separation power of the dynamically coated phase. All investigated compounds were separated into their enantiomers. Compared with a conventionally packed vancomycin-CSP, a reversal of the enantiomer elution order was obtained.

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High-performance liquid chromatographic separation of dihydropyrimidine racemates on polysaccharide-derived chiral stationary phases

Cited by 8 publications

References 22 publications

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

Adsorption Mechanisms in Normal-Phase Chromatography. Mobile-Phase Modifier Adsorption from Dilute Solutions and Displacement Effect

Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative

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