• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.678-682
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• 2010

A doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were applied to the liquid chromatographic resolution of racemic tocainide, an antiarrhythmic agent, and its analogues. The chiral recognition efficiency of the doubly tethered CSP for tocainide and its analogues was generally greater than that of the corresponding singly tethered CSP especially in terms of the resolution ($R_S$). The resolution of tocainide and its analogues on the doubly tethered CSP were dependent on the content and the type of the organic and acidic modifiers in aqueous mobile phase and the column temperature. Especially, the retention behaviors of analytes on the doubly tethered CSP with the variation of the content of organic modifier in aqueous mobile phase were opposite to those on the corresponding singly tethered CSP and these opposite retention behaviors were rationalized by the lipophilicity differences of the two CSPs.

• Journal of the Korean Chemical Society
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• v.55 no.5
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• pp.751-755
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• 2011

A doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of various aryl ${\alpha}$-aminoalkyl ketones with the use of 80% ethanol in water containing 10 mM sulfuric acid as a mobile phase. The chiral resolution was quite successful, the separation factors (${\alpha}$) and the resolutions ($R_S$) being in the range of 1.39-2.05 and 3.18-5.22, respectively. The separation factors (${\alpha}$) on the doubly tethered CSP were slightly worse than those on the corresponding singly tethered CSP. However, the resolutions ($R_S$) on the doubly tethered CSP were generally greater than those on the corresponding singly tethered CSP. The chromatographic behaviors for the resolution of aryl ${\alpha}$-aminoalkyl ketones on the doubly tethered CSP were demonstrated to be dependent on the type and the content of the organic and acidic modifiers in aqueous mobile phase and the column temperature.

• Archives of Pharmacal Research
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• v.26 no.2
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• pp.114-119
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• 2003

A high performance liquid chromatographic (HPLC) method was developed for the qualitative and quantitative determination of benzophenanthridine alkaloids from the methanol extracts of Hylomecon hylomeconoides and H. vernale (Papaveraceae). Achiral and chiral methods were adapted for the separation of 6-methoxydihydrosanguinarine (1), 6-acetonyldihydrosanguinarine (2) and dihydrosanguinarine (3). The achiral reversed phase HPLC method made it possible the simultaneous separation and determination of 1, 2 and 3 within 20 min on ODS column using acetonitrile-phosphate buffer (50 mM, pH 7.0) (50 : 50, v/v). The separation and determination of 1 and 2 enantiomers was available using chiral columns. The same amount of (+) and (-)-enantiomers of 1 was found from the methanol extract of specimen, indicated that 1 could be the artifact produced by the reaction of sanguinarine with methanol. H. hylomeconoides showed higher level of 1 and 3 in compared with H. vernale, especially in root samples permitting the possibility of chemical discrimination between two species.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.314.1-314.1
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• 2003

Examination was made of the urinary metabolite(s) of CKD-712, which is a chiral compound, named S-YS49 derived from higenamine (one component of Aconite spp.) derivatives. First of all. to analyze the metabolite(s) of CKD-712, a simple and sensitive detection method for CKD-712 was developed by using gas chromatography-mass spectrometry(GC/MS). (omitted)

• 한국생물공학회:학술대회논문집
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• 2003.10a
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• pp.549-553
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• 2003

SMB(simulated moving bed) chromatography system has been developed to realize continuous separation and save solvent consumption for binary mixture such as chiral compounds in especial. The parameters of SMB chromatography system can be calculated from mass balance equations of true moving bed chromatography, and they are used in design of 6-column SMB chromatography. We can separate 1'R-25 and 1'S-2S enantiomers as a raffinate product in 95% of purity using assembled SMB chromatography system.

• Bulletin of the Korean Chemical Society
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• v.28 no.11
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• pp.1980-1984
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• 2007

An HPLC chiral stationary phase (CSP) which has only two ureide functional groups was prepared starting from (1S,2S)-1,2-diaminocyclohexane. The CSP was successful in the resolution of various N-(3,5- dinitrobenzoyl)-α-amino acids, the separation (α) and the resolution factors (RS) being within the range of 1.11-1.35 and 2.19-5.17, respectively with the use of 20% 2-propanol in hexane containing 0.1% trifluoroacetic acid as a mobile phase. However, ethyl esters of N-(3,5-dinitrobenzoyl)-α-amino acids were not resolved or resolved with only marginal separation and resolution factors on the CSP under the identical mobile phase condition. From these results, the complexation of the carboxylate anions of analytes inside the double-ureide pocket of the CSP was expected to play some important role for the chiral recognition. In contrast, N-(3,5- dinitrobenzoyl)-α-amino acid N-propylamides were resolved on the CSP with reasonable separation and resolution factors. Enantioselective hydrogen bonding interactions between analytes and the CSP were presumed to be responsible for these resolutions.

• Bulletin of the Korean Chemical Society
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• v.27 no.11
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• pp.1769-1774
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• 2006

A new liquid chromatographic chiral stationary phase based on (2S,3S)-O,O'-bis-(10-undecenoyl)-N,N'-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol was prepared starting from (2R,3R)-1,4-bis(benzyloxy)-2,3-butanediol. The new chiral stationary phase was applied to the resolution of racemic anilide derivatives of N-acetyl-a-amino acids, 1,1'-bi-2-naphthol and 3,3'-diaryl-1,1'-bi-2-naphthols. The CSP was also applied to the resolution of some chiral drugs including a diuretic, bendroflumethiazide, and non-steroidal anti-inflammatory agents such naproxen and alminoprofen. In every case, the chiral recognition efficiency of the new CSP was quite excellent.

• Bulletin of the Korean Chemical Society
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• v.29 no.1
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• pp.257-260
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• 2008

• Bulletin of the Korean Chemical Society
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• v.28 no.6
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• pp.1035-1038
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• 2007

• Bulletin of the Korean Chemical Society
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• v.15 no.1
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• pp.86-88
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• 1994