• 한국식품영양과학회지
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• 제35권7호
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• pp.874-880
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• 2006

건생강 제품의 진위판별을 위한 기초자료를 제공하기 위하여 건조된 생강으로부터 휘발성 향기성분을 추출하여 향기특성을 분석하고, MDGC/MS에 의해 키랄성 휘발성분의 enantiomeric composition을 분석하였다. 건생강에서 총 57종을 동정하였으며 주요 휘발성 향기성분은 zingiberene, ${\beta}-sesquiphellandrene$, ${\beta}-bisabolene$, (E,E)-${\alpha}-farnesene$ 및 ${\alpha}-curcumene$이었다. 건생강에 함유된 키랄성 향기성분 중에서 enaniomeric composition을 측정하기 위해 선택된 키랄화합물 중 ${\alpha}-pinene$ 및 nerolidol은 높은 enantiomeric purity(>96%)로 검출되었으며, ${\beta}-pinene$은 (R)-enantiomer만이 검출되어 특이적이었다. ${\alpha}-Terpineol$은 (R)-enantiomer가 72%로 높게 나타났으며 linalool과 4-terpineol은 두 이성질체가 혼합된 것으로 나타났다. Limonene의 enantiomeric excess(ee, %)는 17.2%로 (S)-enantiomer가 주요 이성질체이었다. 따라서 이러한 키랄성 향기성분의 enantiomeric composition은 건생강의 진위평가를 위한 변수로 사용될 수 있을 것으로 생각된다.

• Bulletin of the Korean Chemical Society
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• 제17권8호
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• pp.673-674
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• 1996

• 한국미생물·생명공학회지
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• 제24권2호
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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.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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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)

• 대한약학회:학술대회논문집
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• 대한약학회 2000년도 NEW STRATEGY FOR DRUG DEVELOPMENT IN POST-GENOMIC ERA(대한약학회)
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• pp.248.1-248.1
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• 2000

• Archives of Pharmacal Research
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• 제23권6호
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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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• 제25권9호
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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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• 제26권6호
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• pp.998-1000
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• 2005

• KSBB Journal
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• 제26권4호
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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.

• 분석과학
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• 제36권4호
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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.