• Journal of the Korean Society of Food Science and Nutrition
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• v.35 no.7
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• pp.874-880
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• 2006

The volatile compounds of Zingiber officinale Roscoe were extracted by simultaneous steam distillation and extraction (SDE) method and identified with gas chromatigraphy/mass spectrometer (GC/MS) analysis. Enantiomeric compositions of chiral compounds were determined by multidimensional gas chromatography/mass spectrometer (MDGC/MS). A total of 57 compounds were indentified and quantified, including zingiberene, ${\beta}-sesquiphellandrene$, ${\beta}-bisabolene$, $(E,E)-{\alpha}-farnesene$ and ${\alpha}-curcumene$. Among them, zingiberene (38.41%) was founds as the predominantly abundant component. ${\alpha}-Pinene$ and nerolidol in dried ginger were detected by high enantiomeric purity (>96%) for (S)-form, and ${\beta}-pinene$ was detected only (R)-form. The enantiomeric composition of ${\alpha}-terpineol$ revealed 72.0% for (R)-form, and linalool and 4-terpineol showed mixtures of both enantiomers. (S)-Enantiomer was the major enantiomer of limonene having enatiomeric excess of 17.2%. Hence the enantiomeric composition of these compounds can be used as parameter for authenticty control of Zingiber officinale.

• Bulletin of the Korean Chemical Society
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• v.17 no.8
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• pp.673-674
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• 1996

• Microbiology and Biotechnology Letters
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• v.24 no.2
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• pp.213-216
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• 1996

Optically active carboxylic acid, D-(-)-$\beta$-hydroxyisobutyric acid {(D)-(-)-HIBA} is a useful chiral starting material for the preparation of enantiomerically pure bioactive compounds which have a chiral methyl carbon center in the molecule such as captopril, $\alpha$-tocopherol, erythromycin A, muscone and so on. (S)-3-Acetoxy-2-methylpropanol can be used as the precursor of (D)-(-)-HIBA, that is, chemical oxidation of the hydroxyl group and subsequent hydrolysis of acyl group in (S)-3-acetoxy-2-methylpropanol affords D-(-)-$\beta$-hydroxyisobutyric acid. (S)-3-Acetoxy-2-methyl-propanol was prepared by lipase-catalyzed asymmetric hydrolysis. In the enzymatic hydrolysis system, lipase AY (Candida rugosa) provided the expected (S)-3-acetoxy-2-methylpropanol in 60% e.e. of the enantiomeric purity under the phosphate buffer and organic co-solvent system.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.219.1-219.1
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• 2003

$^1$H-NMR method for the determination of enantiomeric purity of (S)-(+)-ibuprofen was developed using (-)-cinchonidine as a chiral solvating agent. (S)-(+)-ibuprofen was prepared by optical resolution of racemic ibuprofen using preferential recrystallization method with (S)-(-)-${\alpha}$-methylbenzylamine and (R)-(-)-ibuprofen by semi-preparative chiral HPLC using chiral OD column and n-hexane/2-propanol/trifluoroacetic acid as a mobile phase. Several concentrations of synthetic mixture of (S)-(+)-ibuprofen and (R)-(-)-ibuprofen were added to the (-)-cinchonidine disolved in CDCl$_3$. (omitted)

• Proceedings of the PSK Conference
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• 2000.10a
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• pp.248.1-248.1
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• 2000

• Archives of Pharmacal Research
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• v.23 no.6
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• pp.568-573
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• 2000

A reversed-phase high-performance liquid chromatographic method was developed to determine the optical purity of bevantolol enantiomers. (S)-(-)-Menthyl chloroformate((-)-MCF), (S)-(-)-$\alpha$-methylbenzyl isocyanate((-)-MBIC) and 2,3,4,6-tetra-O-acetyl-$\beta$-D-glucopyranosyl isothiocyanate(GITC), which can react with the secondary amine group of bevantolol were investigated as chiral derivatization reagents. Among them indirect chiral HPLC method using CITC gave the best result. The derivatization proceeded quantitatively within 20 min at room temperature. Separation of the enantiomers as diastereomers was achieved by reversed-phase HPLC within 20min using ODS column. Different ratios of (S)-(-)-bevantolol and (R)-(+)-bevantolol were prepared. Enantiomeric separation of these mixtures took place on a chiralcel OD column or, after derivatization with GITC, on a ODS column. No racemization was found during the experiment. This method allowed determination of 0.05% of either enantiomer in the presence of its stereoisomer and method validation showed adequete linearity over the required range.

• Bulletin of the Korean Chemical Society
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• v.25 no.9
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• pp.1385-1391
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• 2004

A general route for the synthesis of optically active unhindered aliphatic alcohols, where the steric demands between two alkyl groups adjacent to the carbinol are similar, with high enantiomeric purity has been developed by sulfoxifation of chiral ${\beta}$-hydroxy sulfides, followed by alkylation and desulfurization.

• Bulletin of the Korean Chemical Society
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• v.26 no.6
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• pp.998-1000
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• 2005

• KSBB Journal
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• v.26 no.4
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• pp.323-327
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• 2011

The convenient derivatization method of chiral amino alcohols as 9-anthraldimine Schiff base derivatives for chiral resolution was developed and the liquid chromatographic enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives was investigated on several coated and covalently bonded polysaccharide-derived chiral stationary phases (CSPs). In general, the performance of Chiralcel OD-H (or Chiralcel OD) (${\alpha}$ = 1.24-2.89), the coated CSP derived from cellulose derivative was superior to the other CSPs for resolution of 9-anthraldimine derivatives of several amino alcohols. The results of enantioseparation depending on the structure of 9-anthraldimine analytes like the steric bulky group and the polar moiety etc were discussed. The analytical method was applied to measure the enantiomeric purity of commercially available chiral amino alcohols. It is expected that the convenient analytical method will be very efficient for determination of enantiomeric purity of amino alcohols as 9-anthraldimine Schiff base derivatives with strong UV absorption.

• Analytical Science and Technology
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• v.36 no.4
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• pp.143-151
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• 2023

Considering the greater role of α-amino acids in our daily lives, the enantiomer resolution of seven α-amino acids derivatized with fluorogenic reagent (4-fluoro-7-nitro-2,1,3-benzoxadiazole, NBD-F) by chiral HPLC on amylose or cellulose trisphenylcarbamate derived chiral stationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection was performed. The degree of enantioseparation and resolution was affected by nature and selector backbones of the CSPs as well as the kind of amino acids. Baseline enantiomer separation and resolutions were observed for the enantiomers of all analytes as NBD derivatives especially on coated type amylose tris(3,5-dimethylphenylcarbamate) derived CSPs (Chiralpak AD-H and Lux Amylose-1). The other CSPs also showed good enantioselectivity except for the CSPs (Chiralpak IB, Chiralcel OD-H and Lux Cellulose-1) having cellulose tris(3,5-dimethylphenylcarbamate) as chiral selectors. The developed analytical chiral method was applied to determine the enantiomeric purity of seven commercially available L-α-amino acids and the impurities as D-forms were found to be in the range 0.08-0.87 %, respectively. The intra- and interday accuracy and precision assays showed high accuracy and precision of the developed analytical method. This chiral HPLC method for the enantiomer resolution of amino acids using fluorescent derivatization could be useful for the determination of enantiomeric purity of pharmaceuticals and biological study for amino acid type compounds among chiral drugs.