• Journal of the Korean Chemical Society
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• v.39 no.4
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• pp.257-265
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• 1995

Free amino acids were isolated from milk and their absolute amounts were determined by reversed phase high performance liquid chromatography after derivatization with dansyl chloride. The determination of D- and L-amino acids was based on achiral separation on a C18 column. It was found that milk contained totally 41.00 mg DL-amino acids in 100 mL milk. The level of D-amino acids to L-amino acids was determined by a column-switching system combining an achiral reversed phase separation and chiral chelate additive. The chiral separation was carried out with addition of the chiral Cu(N-benzyl-L-proline)2 chelate to the mobile phase in reversed phase liquid chromatography. It was found that the determination of 16 different amino acids is feasible in the milk sample with a C18 column separation and 12 D-amino acids out of the 16 amino acids can be determined via the column-switching system with chiral separation. 2.05% of D-glutamic acid and 2.93% of D-alanine were found in milk.

• Analytical Science and Technology
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• v.22 no.4
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• pp.313-318
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• 2009

Liquid chromatographic enantiomer separation of amino alcohols was performed on several chiral columns based on polysaccharide derivatives under the mobile phase conditions containing acid or base additive. The chromatographic parameters were greatly influenced by the nature of the mobile phase containing acid or base additive as well as the used chiral columns. Compared to chromatographic results obtained in the mobile phase containing base additive (0.1% triethylamine), especially, Chiralcel OD showed dramatically enhanced separation factors and resolution factors with reduced capacity factors under the mobile phase condition containing acidic additive (0.1% trifluoroacetic acid). When the mobile phase containing 0.05% trifluoroacetic acid and 0.05% triethylamine was used on Chiralcel OD, the greatest separation factors and resolution factors among all other mobile phase conditions in this study were observed.

• Bulletin of the Korean Chemical Society
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• v.13 no.3
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• pp.280-285
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• 1992

Enantiomeric separation of free amino acids has been achieved by a reversed phase liquid chromatography with addition of a Cu(Ⅱ) complex of N-alkyl-L-proline (alkyl: propyl, pentyl or octyl) to the mobile phase. The amino acids eluted were detected by a postcolumn OPA system. N-alkyl-L-proline was prepared and used as a chiral ligand of Cu(Ⅱ) chelate for the enantiomeric separation. The concentration of the Cu(Ⅱ) chelate, the organic modifier and pH affect the enantiomeric separation of free amino acids. The retention behaviour, varied with change in pH and the concentration of the Cu(Ⅱ) chelate, was different compared with those of the derivatized amino acids. The elution orders between D- and L-forms were consistent except histidine showing that L-forms elute earlier than D-forms. The retention mechanism for the enantiomeric separation can be illustrated by the stereospecificity of the ligand exchange reaction and the hydrophobic interaction between the substituent of amino acids and reversed phase, $C_18$.

• Archives of Pharmacal Research
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• v.29 no.9
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• pp.808-813
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• 2006

Two methods for the chiral purity determination of bevantolol were developed, namely capillary electrophoresis (CE) using carboxymethyl-${\beta}$-cyclodextrin (CM-${\beta}$-CD) as a chiral selector and high-perfomance liquid chromatography (HPLC) using a chiral stationary phase. In the HPLC method, the separation of bevantolol enantiomers was performed on a Chiralpak AD-H column by isocratic elution with n-hexane-ethanol-diethylamine (10:90:0.1, v/v/v) as mobile phase. In the CE method, bevantolol enantiomers were separated on an uncoated fused silica capillary with 50 mM amonium phosphate dibasic adjusted to a pH 6.5 with phosphoric acid containing 15 mM CM-${\beta}$-CD as running buffer. Validation data such as linearity, recovery, detection limit, and precision of the two methods are presented. The detection limits of S-(-)-bevantolol were 0.1% and 0.05% for CE and HPLC method, respectively and R-(+)-bevantolol were 0.15% and 0.05% for CE and HPLC method, respectively. There was generally good agreement between the HPLC and CE results.

• Bulletin of the Korean Chemical Society
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• v.34 no.10
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• pp.2978-2982
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• 2013

A doubly tethered $N-CH_3$ amide chiral stationary phase (CSP 4) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was applied to the resolution of an antiarrythmic agent, tocainide, and its analogues and the chromatographic resolution results were compared with those on a singly tethered N-H amide CSP (CSP 1), a singly tethered $N-CH_3$ amide CSP (CSP 2) and a doubly tethered N-H amide CSP (CSP 3) under an identical aqueous mobile phase condition. CSP 4 was found to be generally better than other CSPs in terms of the separation factors (${\alpha}$) and resolutions (RS). The retention times of analytes denoted by the retention factors ($k_1$) on CSP 4 were quite long compared to those on other CSPs because of the improved lipophilicity of CSP 4. The long retention times of analytes on CSP 4 were successfully controlled by the addition of a small amount of ammonium acetate to aqueous mobile phase without hurting the chiral recognition efficiency. The variation of the content and type of organic and acidic modifier in aqueous mobile phase was found not to change the chiral recognition efficiency significantly.

• KSBB Journal
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• v.27 no.4
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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.

• Bulletin of the Korean Chemical Society
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• v.27 no.8
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• pp.1222-1224
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• 2006

• Bulletin of the Korean Chemical Society
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• v.27 no.4
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• pp.589-592
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• 2006

• Bulletin of the Korean Chemical Society
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• v.30 no.6
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• pp.1373-1375
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• 2009

• Bulletin of the Korean Chemical Society
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• v.30 no.11
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• pp.2827-2829
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• 2009