Diastereomeric and enantiomeric separation of monoesters prepared from meso-cyclopentanediols and racemic carboxylic acids on a silica phase and on amylose and cellulose chiral stationary phases

Kunath, A.; Theil, Fritz; Wagner, Jürgen

doi:10.1016/s0021-9673(94)89142-7

Cited by 42 publications

(13 citation statements)

References 6 publications

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“…The same variations of retention are observed when 1-propanol is used. This result is consistent with a decreasing ability of the solvent to displace the solute from the CSP, due to a decrease of the solvent polarity [14,15]. As illustrated in Figure 2, the change in the mobile phase modifier from ethanol to 1-propanol results in a k increase of less than 25% whereas the enantioselectivity remains constant and the resolution decreases less than 10%, except for 4 with a supplementary NH group whose resolution increases by 70% (while enantioselectivity remains constant); selective interactions seem to be unaffected by the polarity of the organic modifier.…”

Section: Influence Of the Mobile Phase Compositionsupporting

confidence: 77%

“…When ethanol is replaced by 1-propanol, a decrease in the retention factors k, enantioselectivity a, and resolution R s is obtained. This unusual effect confirms that, for this solute, the retention mechanism does not depend on hydrogen bonding [15,32]. Use of 2-propanol instead of 1-propanol results in an increase in k for all solutes.…”

Section: Influence Of the Mobile Phase Compositionsupporting

confidence: 75%

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Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases

Danel

Foulon

Park

et al. 2005

J of Separation Science

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Analytical HPLC methods using derivatized cellulose chiral stationary phases were developed for the direct enantioseparation of substituted [1-(imidazo-1-yl)-1-phenylmethyl)]-benzothiazolinone and benzoxazolinone derivatives with one chiral center. Those analogues of fadrozole constitute new potent nonsteroidal inhibitors of aromatase (P450 arom). The separations were made using normal phase methodology with a mobile phase consisting of n-hexane-alcohol (ethanol, 1-propanol, or 2-propanol) in various proportions, and a silica-based cellulose tris-3,5-dimethylphenylcarbamate (Chiralcel OD-H), or tris-methylbenzoate (Chiralcel OJ). The effects of concentration of various aliphatic alcohols in the mobile phase were studied. A better separation was achieved on cellulose carbamate phase compared with the cellulose ester phase. The effects of structural features of the solutes along with the temperature of the column on the discrimination between the enantiomers were examined. Baseline separation (Rs > 1.5) was easily obtained in many cases.

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Section: Influence Of the Mobile Phase Compositionsupporting

confidence: 77%

Section: Influence Of the Mobile Phase Compositionsupporting

confidence: 75%

Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases

Danel

Foulon

Park

et al. 2005

J of Separation Science

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“…As expected from the higher polarity of ethanol compared with 2-propanol (Kunath et al, 1994), an increase in the retention factor, k, was observed on changing the mobile phase modifier from ethanol (eluents N, O and P) to 2-propanol (eluents Q, R and S). For example, on Chiralcel OD-H the parameters (k, α, R S ) obtained with pronucleotide 2 were 1.35, 1.11, n.r.…”

Section: Effects Of the Mobile Phase On Retention And Stereoselectivitysupporting

confidence: 62%

“…Separation of compounds by chiral HPLC is now well established with over 100 different chiral stationary phases (CSP) commercially available. Among them cellulose and amylose ester and carbamate derivatives coated onto large pore silica gel backbones have proved to be extremely useful stationary phases for chiral resolution (Shibukawa and Nakagawa, 1989;Okamoto and Kaida, 1994;Liu et al, 1994;Aboul-Enein et al, 1994;Kunath et al, 1994, Kirkland, 1995Oguni et al, 1995;Okamoto and Yashima, 1998).…”

Section: Introductionmentioning

confidence: 99%

Column selection and method development for the separation of nucleoside phosphotriester diastereoisomers, new potential anti‐viral drugs. Application to cellular extract analysis

Goossens¹,

Foulon²,

Villard³

et al. 2005

Biomedical Chromatography

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Analytical HPLC methods using derivatized cellulose and amylose chiral stationary phases used in normal and reversed-phase modes were developed for the diastereoisomeric separation of mononucleotide prodrugs (pronucleotides) of 3'-azido-2',3'-dideoxythymidine (AZT). The resolutions were performed with two silica-based celluloses using normal and reversed-phase methodologies: Tris-3,5-dimethylphenylcarbamate (Chiralcel OD-H and Chiracel OD-RH) and Tris-methylbenzoate (Chiralcel OJ and OJ-R). Two amyloses phases, Tris-3,5-dimethylphenylcarbamate (Chiralpak AD) and Tris-(S)-1-phenylethylcarbamate (Chiralpak AS), were used in normal-phase mode. Additionally, we developed separation using two stationary phases with immobilized cyclodextrins in reversed-phase and polar-organic modes. The mobile phase and the chiral stationary phase were varied to achieve the best resolution. Different types and concentration of aliphatic alcohols, acetonitrile or water in the mobile phase were also tested for the different separation modes. An optimal baseline separation (Rs > 1.5) was readily obtained with all silica-based celluloses and amyloses using a normal-phase methodology. The different columns gave complementary results in term of resolution. Limits of detection and quantification were 0.12-0.20 and 0.40-0.67 microm, respectively. This analytical method was applied in a preliminary study for the pronucleotide 2 quantification in cellular extract.

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“…The results were due likely to the steric differences between the two solvent molecules, leading to quite different chiral surfaces on the stationary phases. 27,29 From these results, we concluded that the addition of a polar additive was essential to obtain satisfactory enantioselectivity for OPs and the selection of the additive depended not only on the compound tested but also on the column used. …”

Section: Influence Of Mobile Phase Compositionmentioning

confidence: 97%

Separation and aquatic toxicity of enantiomers of 1‐(substituted phenoxyacetoxy)alkylphosphonate herbicides

Zhou

Zhao

et al. 2007

Chirality

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A series of organophosphorous compounds (OPs), 1-(substituted phenoxyacetoxy)alkylphosphonates containing a chiral carbon atom, show notable herbicidal activities. In this study, the enantioselective separation and biological toxicity of all these compounds were investigated. The enantioselective separation on the columns of Chiralpak AD, Chiralpak AS, Chiralcel OD, and Chiralcel OJ were compared under various chromatographic conditions. All the analytes investigated obtained baseline resolution (R(s) > 1.5) on Chiralpak AD column, which showed best chiral separation capacity. Further investigation was carried out on Chiralpak AD to evaluate the influence of the mobile phase composition and column temperature. The effect of the structural features on discrimination was also examined. The resolved enantiomers were distinguished by their signs of circular dichroism. The acute aquatic toxicity of enantiomers and racemate to Daphnia magna (D. magna) were assessed. The in vivo assays showed that compound 3 was about 2-148.5 times more toxic than the other four analogues to D. magna. The racemates of compounds 3 and 5 showed intermediate toxicity compare to their enantiomers, while those of compounds 1, 2, and 4 showed synergistic or antagonistic effect. These results suggest that the biological toxicity of chiral OPs to nontarget organisms is enantioselective and therefore should be evaluated with their pure enantiomers.

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Diastereomeric and enantiomeric separation of monoesters prepared from meso-cyclopentanediols and racemic carboxylic acids on a silica phase and on amylose and cellulose chiral stationary phases

Cited by 42 publications

References 6 publications

Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases

Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases

Column selection and method development for the separation of nucleoside phosphotriester diastereoisomers, new potential anti‐viral drugs. Application to cellular extract analysis

Separation and aquatic toxicity of enantiomers of 1‐(substituted phenoxyacetoxy)alkylphosphonate herbicides

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