High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase

Berkecz, Róbert; Sztojkov‐Ivanov, Anita; Ilisz, István; Forró, Enikő; Fülöp, Ferenc; Hyun, Myung Ho; Péter, Antal

doi:10.1016/j.chroma.2006.06.064

Cited by 57 publications

(32 citation statements)

References 16 publications

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“…Retention factors (k 1 ) on CSP 2 are also greater than those on CSP 1 except for the resolution of 3-amino-4,4-diphenylbutyric acid (8) and 3-aminoadipic acid (13). These retention behaviors on CSP 1 and CSP 2 are somewhat different from those for the resolution of a-amino acids, amines, and amino alcohols.…”

Section: Resultsmentioning

confidence: 88%

“…The elution orders shown in Table 1 were determined by injecting configurationally known samples. In the case of 3-aminobutyric acid (12) and 3-aminoadipic acid (13), configurationally known samples were not available and consequently the elution orders could not be determined.…”

Section: Resultsmentioning

confidence: 99%

“…16 Both enantiomers of the b-amino acids 3-11 shown in Figure 2 were purchased from Peptech (Cambridge, MA, USA). 3-Aminobutyric acid (12) and 3-aminoadipic acid (13) shown in Figure 2 were available as racemates from Aldrich. Injection samples were prepared by dissolving each analyte (racemic and 1:1 mixture of optically active analytes) in water at a concentration of 1 mg/ml.…”

Section: Methodsmentioning

confidence: 99%

“…1) by bonding (1)-(18-crown-6)-2,3,11,12-tetracarboxylic acid incorporating two tartaric acid unit to 3-aminopropylsilica gel. 10 CSP 1 was quite successful in the resolution of various racemic primary amino compounds including a-amino acids, 10 b-amino acids, [11][12][13] racemic amines, 14 racemic amino alcohols, 14 and racemic fluoroquinolone antibacterials. 15 The resolution of racemic primary amino compounds on CSP 1 has been usually performed under highly acidic conditions with an aqueous mobile phase containing sulfuric acid or acetic acid in order to convert the primary amino group into primary ammonium ions (R-NH 3 1 ), which are essential for chiral recognition by chiral crown ethers.…”

Section: Introductionmentioning

confidence: 99%

“…However, CSP 2 has not yet been applied to the resolution of b-amino acids while CSP 1 has been found useful for the resolution of b-amino acids. [11][12][13] Optically active b-amino acids have attracted considerable attention due to their potent pharmacological activities and their usefulness as building blocks of many natural products. 17,18 In this instance, analytical methods for the exact determination of the enantiomeric composition of b-amino acids are essential and liquid chromatographic chiral separations on CSPs might be the method of choice.…”

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confidence: 99%

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Liquid chromatographic direct resolution of β‐amino acids on a doubly tethered chiral stationary phase containing NH amide linkage based on (+)‐(18‐crown‐6)‐ 2,3,11,12‐tetracarboxylic acid

2007

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A doubly tethered chiral stationary phase (CSP) prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to doubly tethered primary aminoalkyl silica gel was used for the resolution of various beta-amino acids. All the beta-amino acids tested were resolved quite well, the separation (alpha) and the resolution factors (RS) being in the ranges 1.34-2.09 and 2.52-7.45, respectively, with a mobile phase of methanol-water (50:50, v/v) containing 10 mM acetic acid. The chiral recognition efficiency of the doubly-tethered CSP was found to be generally superior to that of the corresponding singly-tethered CSP in the resolution of beta-amino acids. The chiral recognition behaviors for the resolution of beta-amino acids on the doubly tethered CSP were examined by varying the type and content of organic and acidic modifiers in the aqueous mobile phase and the column temperature.

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Liquid chromatographic direct resolution of β‐amino acids on a doubly tethered chiral stationary phase containing NH amide linkage based on (+)‐(18‐crown‐6)‐ 2,3,11,12‐tetracarboxylic acid

2007

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Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Dołowy

Pyka

2013

Biomedical Chromatography

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Amino acids are very important organic compounds in nature. The biological activity of amino acids depends mainly on their stereoisomeric configuration (d- or l-). Thus, the stereochemical analysis of amino acids and peptides is an important aspect of their characterization. Owing to the increasing role of amino acid configuration in biomedical and pharmaceutical studies, numerous analytical methods have been described in the literature. Among a wide range of analytical techniques available for the steroselective separation of different amino acids, which were obtained from plants or biological samples, chromatographic methods such as thin-layer chromatography, high-performance chromatography and also gas chromatography are very useful. This review presents such systems developed for direct stereoisomeric separation and quantitative determination of amino acid and peptide enantiomers with emphasis on selected literature published during two last decades. Almost all aspects, including sample preparation prior chromatographic analysis, stationary phase, solvent system and detection system, are discussed. New possibilities in chiral amino acid analysis have been opened up by the application of mass spectrometry and infrared detection in thin-layer chromatography and mass spectrometry-selected ion monitoring detection system in gas chromatography. A modern trend in high-performance chromatography is two-dimensional chromatography. These innovations have led to decreased development time and increased amino acid resolution and detectability.

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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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High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase

Cited by 57 publications

References 16 publications

Liquid chromatographic direct resolution of β‐amino acids on a doubly tethered chiral stationary phase containing NH amide linkage based on (+)‐(18‐crown‐6)‐ 2,3,11,12‐tetracarboxylic acid

Liquid chromatographic direct resolution of β‐amino acids on a doubly tethered chiral stationary phase containing NH amide linkage based on (+)‐(18‐crown‐6)‐ 2,3,11,12‐tetracarboxylic acid

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

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

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