Investigation of the structure–selectivity relationships and van’t Hoff analysis of chromatographic stereoisomer separations of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on Cinchona alkaloid-based chiral stationary phases

Ilisz, István; Gecse, Zsanett; Lajkó, Gyula; Nonn, Melinda; Fülöp, Ferenc; Lindner, Wolfgang; Péter, Antal

doi:10.1016/j.chroma.2015.01.041

Cited by 15 publications

(13 citation statements)

References 46 publications

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“…The calculated thermodynamic parameters were found to depend on the structures of the SAs and the SOs employed. Structure-selectivity relationships were investigated through the enantiomeric separations of isoxazoline-fused aminocyclopentanecarboxylic acids [45]. SAs with methyl substituents in most cases interacted more strongly than ethyl-substituted ones with the SO, which resulted in higher selectivity and resolution.…”

Section: Recent Applicationsmentioning

confidence: 99%

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

Ilisz

Péter

Lindner

2016

TrAC Trends in Analytical Chemistry

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This review discusses recent publications on the separation and analysis of natural and unnatural amino acid enantiomers by liquid chromatography. Focus is placed on methodological aspects relating chiral stationary phases and chiral columns which can cope with the challenge. Conceptually, amino acids can be enantioseparated in free form, which refers to the resolution of polar ampholytes, or as N-protected amino acids, which can be regarded as acidic commodities. Such synthons are used, for instance, in peptide synthesis protocols. Amino groups are frequently tagged with highly fluorescent or MS/MS active labels in order to generate sensitive and simultaneously stereoselective assays of diverse amino acids in complex matrices. It is our intention to present the state of the art of enantioselective amino acid analysis by HPLC concepts and to pinpoint practical aspects.

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Section: Recent Applicationsmentioning

confidence: 99%

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

Ilisz

Péter

Lindner

2016

TrAC Trends in Analytical Chemistry

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“…Although the separation conditions of individual amino acids were not optimized, very high resolution values of up to R S = 22.7 were observed. Thus, for the present set of analytes, CE enantioseparations may complement the reported HPLC enantioseparations on various CSPs .…”

Section: Discussionmentioning

confidence: 75%

“…Recently, the enantioseparation of isoxazoline‐fused 2‐aminocyclopentanecarboxylic acids (Fig. , compounds of the A series) was investigated by HPLC using macrocyclic glycopeptide antibiotics as chiral selectors including vancomycin, vancomycin aglycone, teicoplanin and teicoplanin aglycone , zwitterionic Cinchona alkaloid‐based chiral stationary phases (CSPs) , a chiral ligand‐exchange CSP based on N ‐(( R )‐2‐hydroxy‐1‐phenylethyl)‐ N ‐undecylaminoacetate as well as a (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid‐derived CSP . In addition, (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid was also used as a chiral solvating agent to study the bicyclic isoxazoline β‐amino acids by NMR .…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin‐mediated capillary electrophoresis enantioseparation of dansylated β‐amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures

et al. 2019

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The present study investigated the separation of bicyclic β‐amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures by capillary electrophoresis using native cyclodextrins as well as neutral and charged derivatives as chiral selectors. The amino acids were derivatized with dansyl chloride to provide a UV chromophore. Separations were carried out at 20°C in a 48.5/40 cm, 50 µm fused‐silica capillary at an applied voltage of 20 kV. Fifty millimolar sodium phosphate background electrolytes pH 2.5 and 7.2 containing either 5 or 30 mg/mL of the CDs were used. For the majority of the investigated CDs, enantioseparations could only be achieved at pH 2.5 when the analytes are positively charged. Successful enantioseparations as negatively charged analytes at pH 7.2 were only observed for few compounds. In the case of methyl‐γ‐cyclodextrin, opposite enantiomer migration order was observed in pH 2.5 or 7.2 background electrolytes. Dependence of the enantiomer migration order on the size of the cavity of the cyclodextrins was also found. Furthermore, the degree of methylation of β‐cyclodextrin derivatives affected the migration order of several analyte enantiomers.

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“…In 1999 a set of new CSPs predominantly based on tert ‐butyl carbamates of Cinchona alkaloids were prepared and evaluated within the Lindner's group . In an attempt to overcome the limited applicability scope of WAX phases corresponding zwitterionic ion‐exchange‐type CSPs were proposed, synthesized and extensively evaluated . The zwitterionic phases allow enantiomer separation of a wide range of chiral ionizable compounds comprising not only acids but also bases and zwitterionic analytes.…”

Section: Introductionmentioning

confidence: 99%

Immobilized strychnine as a new chiral stationary phase for HPLC

et al. 2017

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A new ion-exchanger type chiral stationary phase for high-performance liquid chromatography was prepared. The synthetic protocol is based on derivatization of silica with (3-iodopropyl)trimethoxysilane in the first step followed by immobilization of strychnine via quaternization of nitrogen atom of the alkaloid strychnine. The synthesized chiral stationary phase was chromatographically characterized. The main effort was headed towards the evaluation of the enantioselectivity of the novel sorbent. For that purpose a set of suitable chiral probes, specifically, binaphthyl derivatives, was employed. The influence of methanol content, concentration of aqueous ammonium acetate buffer, and its pH on retention factors, separation selectivity, and resolution of the atropoisomers of the mentioned chiral solutes was studied in detail. It was demonstrated that the new chiral stationary phase was capable to separate atropoisomers of four out of seven testing compounds. Despite the strong influence of the above mentioned variables on retention, their impact on selectivity and resolution was rather moderate. Concerning retention mechanism, it seems that electrostatic interaction between the positively charged quaternary nitrogen of the chiral stationary phase and anionic solute participates significantly in the retention process.

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Investigation of the structure–selectivity relationships and van’t Hoff analysis of chromatographic stereoisomer separations of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on Cinchona alkaloid-based chiral stationary phases

Cited by 15 publications

References 46 publications

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

Cyclodextrin‐mediated capillary electrophoresis enantioseparation of dansylated β‐amino acids with bicyclo[2.2.2]octane, bicyclo[3.1.1]heptane and cyclopenta[d][1,2]oxazole core structures

Immobilized strychnine as a new chiral stationary phase for HPLC

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