• Bulletin of the Korean Chemical Society
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• 제27권10호
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• pp.1577-1580
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• 2006

The article reports the synthesis and enantiomeric recognition of a new chiral azophenolic pyridino-18-crown-6 ether, (S,S)-6, possessing diphenyl groups as chiral barriers. The association constants for the enantiomeric recognition of chiral primary amines (7-12) using chiral azophenolic pyridino-18-crown-6 ether, (S,S)-6, were determined by UV-visible titration method in acetonitrile at $25{^{\circ}C}$.

• Bulletin of the Korean Chemical Society
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• 제26권8호
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• pp.1153-1163
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• 2005

Crown ether-based HPLC chiral stationary phases (CSPs) have been successfully utilized in the resolution of various racemic compounds containing a primary amino group. Especially, CSPs based on chiral crown ethers incorporating chiral binaphthyl unit or tartaric acid unit and based on phenolic pseudo chiral crown ethers have shown high chiral recognition efficiency. In this account paper, a review on the development of crown etherbased HPLC CSPs, their structural characteristics and applications to the resolution of racemic compounds including chiral drugs containing a primary or secondary amino group with the variation of the type and the content of mobile phase components and with the variation of the column temperature is presented.

• Bulletin of the Korean Chemical Society
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• 제33권10호
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• pp.3481-3484
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• 2012

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.285.1-285.1
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• 2003

ChiroSil RCA(+) and SCA(-) HPLC chiral stationary phases (CSPs) developed by covalently bonding (+)- and (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-T A) to silica gel were employed for enantioresolution of racemic amino compounds, respectively. Also, these 18-C-6-TA covalently bonded CSPs were compared to a commercially available Crownpak CR CSP prepared by coating chiral crown ether as a chiral selector on ODS column. (omitted)

• 통합자연과학논문집
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• 제9권1호
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• pp.28-34
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• 2016

A number of chiral selectors have been developed and applied for enantiomer separation of a variety of chiral compounds. Among these chiral selectors are chiral crown ethers, a class of synthetic host polyether molecules that bind protonated chiral primary amines with high selectivity and affinity. In this paper, two important chiral crown ethers as chiral selectors of bis-(1,1'-binaphthyl)-22-crown-6 and (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) are focused. They have been widely used to resolve the enantiomers of chiral compounds containing a primary amino moiety using chiral stationary phases (CSPs) or chiral selectors by high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and so on in chirotechnology. Also, it was described that the commercially available covalent type HPLC CSPs derived from (+)- and (-)-18-C-6-TA have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• Bulletin of the Korean Chemical Society
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• 제28권11호
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• pp.2015-2019
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• 2007

The article reports the synthesis of a novel bispyridino-18-crown-6 ether, 7-{[(5S,15S)-5,15-diphenyl- 3,6,14,17-tetraoxa-23,24-diazatricyclo[17.3.1.18,12]tetracosa-1(23),8(24),9,11,19,21-hexaen-10-yl]oxy}heptylferrocenamide 6, bearing the C2-symmetric diphenyl substituents as chiral barriers and the ferrocenyl groups serving as an electrochemical sensor, and its electrochemical study with D- and L-AlaOMe·HCl as the guest by cyclovoltametry.

• Bulletin of the Korean Chemical Society
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• 제23권4호
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• pp.543-544
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• 2002

• KSBB Journal
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• 제27권4호
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• pp.199-206
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• 2012

Chiral crown ethers are synthetic macrocyclic polyethers that bind protonated chiral primary amines with high selectivity and affinity. They have been widely used to separate or distinguish the enantiomers of chiral compounds containing a primary amino moiety by high-performance liquid chromatography, capillary electrophoresis, and NMR spectroscopy. In this paper, two important chiral crown ethers including chiral binaphthyl unit and (18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selectors are focused. And several chiral resolution techniques and their applications in chirotechnology using these chiral crown ethers with related chiral recognition mechanism studies are reviewed. Especially, it was shown that the commercially available HPLC columns based on (18-crown-6)-2,3,11,12-tetracarboxylic acid have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

• KSBB Journal
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• 제27권4호
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• pp.232-236
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• 2012

Comparative liquid chromatographic enantiomer separation of ${\alpha}$-amino acids, their esters and primary amino compounds was performed using two chiral stationary phases (CSPs) prepared by covalently bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) of the same chiral selector. In general, the separation factors and resolution factors for these analytes on CSP 1 were greater than on CSP 2, while these capacity factors on CSP 2 were quite greater than on CSP 1. Except for leucine methyl ester and phenylalanine methyl ester, the elution orders of all analytes including ${\alpha}$-amino ${\alpha}$-alkyl acids and phenylglycine alkyl esters on CSP 1 are identical to those on CSP 2. This study showed that different connecting structures for these two CSPs might influence their ability to resolve the analytes depending on their structures related to the chiral recognition mechanism.

• Bulletin of the Korean Chemical Society
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• 제28권12호
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• pp.2531-2534
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• 2007