• YAKHAK HOEJI
• /
• v.53 no.2
• /
• pp.60-68
• /
• 2009

In terms of chiral issue, two enantiomers of chiral drugs often differ significantly in their pharmacological, toxicological and pharmacokinetic profile. Chiral switches of racemic drugs have been redeveloped as single enantiomers. Several chiral resolution techniques in chirotechnology are introduced and the most used chiral HPLC chromatographic method among several chiral analysis techniques is described with its several advantages. Several types of chiral HPLC columns derived from their chiral selectors are discussed with their property and applications for enantiomer separation.

• Proceedings of the PSK Conference
• /
• 2002.10a
• /
• pp.167-168
• /
• 2002

Because of the differences between biological and pharmacological properties of chiral drugs in human body, accurate determinations of their optical purities have been in great need. There are two major approaches in chiral separation: indirect method performed under achiral condition, and direct method under the chiral environment. We have been conducting chiral separation of acidic chiral compounds and also amino acidic chiral compounds employing indirect GC methods and direct CE enantiomeric separation methods. (omitted)

• Proceedings of the PSK Conference
• /
• 2002.10a
• /
• pp.399.2-399.2
• /
• 2002

Capillary electrophoretic direct chiral separation method is described for the determination of the absolute configuration of chiral aromatic acids, The enantiomeric separation was achieved by capillary electrophoresis using HP $\beta$-cyclodextrin (CD) as the chiral selector. The effect of CD concentration was investigated to optimize the chiral separation and resolution. When applied to microbial culture fluid. the present method allowed positive identification of chiral aromatic acids and their chirality as well.

• Bulletin of the Korean Chemical Society
• /
• v.16 no.4
• /
• pp.305-309
• /
• 1995

The enantiomeric separation of several amino acid derivatives by reversed-phase liquid chromatography using two (R)-and (S)-naphthylethylcarbamate-β-cyclodextrin(NEC-β-CD) bonded stationary phases was studied to illustrate the chiral recognition model of the enantiomeric separation. The retention and enantioselectivity of the chiral separations with (R)-and (S)-NEC-β-CD bonded phases were compared with similar separations with the native β-CD stationary phases. Especially, the enantioselectivity and elution orders between the derivatized amino acid enantiomers are carefully examined. These results can be illustrated by the chiral recognition models involving inclusion complexation, π-π interaction, and/or hydrophobic interaction. Inclusion complexation and hydrophobic interaction of the naphthyl group of the NEC moiety seem to be major chiral recognition components in the enantiomeric separation of 2,4-dinitrophenyl amino acids and dabsyl amino acids on (R)-and (S)-NEC-β-CD columns. For dansyl amino acids, only the inclusion complexation is the dominant factor. Three different chiral recognition models containing π-π interaction, inclusion complexation and hydrogen bonding were proposed for the separation of the 3,5-dinitrobenzoyl amino acid enantiomers, depending on the size and shape of amino acids.

• Bulletin of the Korean Chemical Society
• /
• v.33 no.8
• /
• pp.2651-2656
• /
• 2012

Sulfonated cellulose tris(3,5-dimethylphenylcarbamate) (SCDMPC)-coated zirconia monolith (ZM) was used as the chiral stationary phase in capillary electrochromatography for separation of enantiomers of ten chiral compounds in acetonitrile (ACN)-phosphate buffer mixtures as the eluent. Influences of the ACN content, buffer concentration and pH on chiral separation have been investigated. Separation data on SCDMPC-ZM have been compared with those on CDMPC-ZM. Resolution factors were better on SCDMPC-ZM than CDMPC-ZM while retention factors were in general shorter on the former than the latter. Best chiral resolutions on SCDMPC-ZM were obtained with the eluent of 50% ACN containing 50 mM phosphate at pH around 4.

• Bulletin of the Korean Chemical Society
• /
• v.23 no.11
• /
• pp.1677-1679
• /
• 2002

• Bulletin of the Korean Chemical Society
• /
• v.34 no.6
• /
• pp.1809-1813
• /
• 2013

Sulfated ${\beta}$-cyclodextrin (SCD)-coated zirconia monolith was used as the chiral stationary phase in capillary electrochromatography for enantiomeric separation of basic chiral compounds. SCD adsorbed on the zirconia surface provided a stable chiral stationary phase in reversed-phase eluents. Retention, chiral selectivity and resolution of a set of six basic chiral compounds were measured in eluents of varying pH, composition of methanol and buffer. Optimum mobile phase condition for the separation of the compounds was found to be methanol content of 30%, buffer concentration of 30 mM and pH of 4.0.

• Analytical Science and Technology
• /
• v.37 no.5
• /
• pp.306-314
• /
• 2024

This study describes the liquid chromatographic enantiomer separation of three typical chiral amines (α-methylbenzylamine, 2-amino-4-methyl-1-pentanol, and 1-methylheptylamine) as 2-hydroxynaphthaldimine derivatives using six amylose trisphenylcarbamates derived chiral stationary phases (CSPs). It was observed that the structural nature of three chiral amines and the structures of amylose chiral selectors can affect their chiral recognition ability. Among the three analytes as 2-hydroxynaphthaldimine derivatives, in general, the greatest enantioselectivities of aromatic amine analyte (α-methylbenzylamine) were achieved on amylose trisphenylcarbamate derived CSPs and were followed by amino alcohol analyte (2-amino-4-methyl-1-pentanol), and aliphatic amine analyte (1-methylheptylamine). Also, the enantiodiscrimination abilities obtained on the two CSPs, Chiralpak ID and Chiralpak IF, were selectively higher than the other four amylose trisphenylcarbamate derived CSPs for the studied analytes. The underlying chiral recognition mechanism between 2-amino-4-methyl-1-pentanol as 2-hydroxynaphthaldimine derivatives and amylose tris(3,5-dimethylphenylcarbamate) chiral selector of Chiralpak AD-H and Lux Amylose-1 was elucidated by molecular docking study, and it was observed that the intermolecular hydrogen bonding interactions by hydroxyl moiety on the amino alcohol analyte as 2-hydroxynaphthaldimine derivatives were the main interactive forces driving the chiral separation. The obtained binding energies between 2-amino-4-methyl-1-pentanol analyte as 2-hydroxynaphthaldimine derivative and amylose tris(3,5-dimethylphenylcarbamate) chiral selector were in agreement with the experimentally determined enantioseparation and elution order by chiral HPLC.

• Journal of Integrative Natural Science
• /
• v.9 no.1
• /
• pp.28-34
• /
• 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.

• Biotechnology and Bioprocess Engineering:BBE
• /
• v.5 no.1
• /
• pp.17-22
• /
• 2000

The separation of tryptophan enantiomers was carried out with medium-pressure liquid chromatography using BSA (bovine serum albumin)-bonded silica as a chiral stationary phase. The influence of various experimental factors such as pH and ionic strength of mobile phase, separation temperature, and the presence of organic additives on the resolution was studied. In order to expand this system to preparative scale, the loadability of sample and the stability of stationary phase for repeated use were also examined. The separation of tryptophan enantiomers was successful with this system. The data indicated that a higher separation factor (a) was obtained at a higher pH and lower temperature and ionic strength in mobile phase. Addition of organic additives (acetonitrile and 2-propanol) in mobile phase contributed to reduce the retention time of L-tryptophan. About $30\%$ of the separation factor was reduced after 80 days of repeated use.