Enantiomer separation of hydrophobic amino compounds by high-performance liquid chromatography using crown ether dynamically coated chiral stationary phase

Machida, Yoshio; Nishi, Hiroyuki; Nakamura, Kouji

doi:10.1016/s0021-9673(98)00896-6

Cited by 57 publications

(20 citation statements)

References 19 publications

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“…This type of phase has been commercialized by Daicel (Tokyo, Japan) under the name Chirapack CR(+) and has found application to the chiral separation of amino acids and various primary amines [148,149] and unusual b-alkyl-amino acids [150,151]. One problem with this coated phase is stability.…”

Section: Synthetic Chiral Macrocyclesmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

226

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Synthetic Chiral Macrocyclesmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

226

135

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“…Recently, high performance liquid chromatography (HPLC) with chiral stationary phase (CSP) has extensively been used to directly separate enantiomers in optical purity test. Enantiomeric amines are usually separated by chiral crown ether columns, [1][2][3][4][5][6] while various racemic amino acids can effectively be separated using CSP chemically immobilized by (1)-18-crown-6 tetracarboxylic acid [(1)-18C6H 4 ; Fig. 1] on silica gel.…”

Section: Introductionmentioning

confidence: 99%

Guest‐dependent conformation of 18‐crown‐6 tetracarboxylic acid: Relation to chiral separation of racemic amino acids

Nagata¹,

Nishi²,

Kamigauchi

et al. 2008

Chirality

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(+)-18-crown-6 tetracarboxylic acid (18C6H(4)) has been used as a chiral selector for various amines and amino acids. To further clarify the structural scaffold of 18C6H(4) for chiral separation, single crystal X-ray analysis of its glycine(+) (1), H3O+ (2), H5O2+ (3), NH4+ (4), and 2CH3NH3+ (5) complexes was performed and the guest-dependent conformation of 18C6H(4) was investigated. The crown ether ring of 18C6H4 in 3, 4, and 5 took a symmetrical C2 or C2-like conformation, whereas that in 1 and 2 took an asymmetric C1 conformation, which is commonly observed in complexes with various optically active amino acids. The overall survey of the present and related complexes suggests that the molecular conformation of 18C6H4 is freely changeable within an allowable range, depending on the molecular shape and interaction mode with the cationic guest. On the basis of the present results, we propose the allowable conformational variation of 18C6H4 and a possible transition pathway from its primary conformation to the conformation suitable for chiral separation of racemic amines and amino acids.

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“…Effect of the salt concentration in the mobile phase Machida et al (1999) studied the changes in retention of basic substances on dynamically coated crown ether stationary phases and assigned them to the sum of two mechanisms: (a) competition between the analyte and the buffer cation for the entrance inside the crown ether cavity; and (b) ion pair formation between the analyte and the counter anion. When the competition is dominant, retention decreases, whereas when the ion pair formation is dominant, it increases (Machida , 1999).…”

Section: Methods Developmentmentioning

confidence: 99%

LC‐MS/MS determination of cinacalcet enantiomers in rat plasma on Chirobiotic V column in polar ionic mode: application to a pharmacokinetic study

Ramisetti

Sravan

2014

Biomedical Chromatography

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A simple and selective polar ionic liquid chromatography-tandem mass spectrometric method for separation and determination of cinacalcet enantiomers in rat plasma was developed and validated. The chromatographic separation was accomplished on a Chirobiotic V column packed with vancomycin as a chiral stationary phase using 2.5 mm ammonium formate in 100% methanol as a mobile phase in an isocratic mode of elution at a flow rate of 1.0 mL/min. The analytes were extracted from rat plasma by precipitating the proteins with acetonitrile. The developed method exhibited a linear dynamic range over 0.5-500 ng/mL in rat plasma for both enantiomers. The method was successfully applied to study the pharmacokinetics after a single dose by oral administration of 10 mg/kg of cinacalcet enantiomers to healthy male Wistar rats.

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Enantiomer separation of hydrophobic amino compounds by high-performance liquid chromatography using crown ether dynamically coated chiral stationary phase

Cited by 57 publications

References 19 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Guest‐dependent conformation of 18‐crown‐6 tetracarboxylic acid: Relation to chiral separation of racemic amino acids

LC‐MS/MS determination of cinacalcet enantiomers in rat plasma on Chirobiotic V column in polar ionic mode: application to a pharmacokinetic study

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