• Journal of Microbiology and Biotechnology
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• v.14 no.4
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• pp.766-771
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• 2004

Julong 601, a Gram-positive anaerobic bacterium strain capable of cleaving the C-ring of isoflavones daidzein and genistein, was isolated from human feces. BLAST search revealed that its complete 16S rDNA gene sequence has 99% similarity to Eubacterium ramulus. Metabolites of daidzein and genistein were determined as O-desmethylangolensin (O-Dma) and 2-(4-hydroxyphenyl) propionic acid (2-HPPA), respectively, based on UV, EI-MS, and $^1H$ and ^{13}C$ NMR spectral analyses. Enantiomers of O-Dma and 2-HPPA were isolated by chiral stationary-phase HPLC (CSP HPLC). Cleavage of the C-ring of daidzein and genistein by strain Julong 601 was highly enantioselective. Specific rotation ([$\alpha]_D$) and circular dichroism (CD) spectra of the enantiomers are reported here for the first time. Biotransformation kinetics of daidzein and genistein indicated that the C-ring of genistein has a higher susceptibility to bacterial degradation than that of daidzein.

• Journal of the Korean Chemical Society
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• v.30 no.2
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• pp.216-223
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• 1986

Separation of optical isomers of DNS derivatized amino acids by a reversed-phase high-performance liquid chromatography has been studied by adding a complex of an optically active amino acid (L-arginine) with the metal ion (Cu(II), Zn(II), Cd(II), Ni(II)) to the mobile phase. The separations are affected by the concentrations of acetonitrile, chelate and buffer. They are also affected by the pH and the kinds of metal and buffer. A separation mechanism, which is based on steric effect of the ligand exchange reaction for the formation of ternary complexes by the D,L-DNS-amino acids and the chiral additive associated with the stationary phase, is proposed to interpret the elution behaviors of D, L-dansyl-amino acids.

• Journal of the Korean Chemical Society
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• v.58 no.3
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• pp.277-282
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• 2014

The optical purity of 11 commercial dexibuprofens and 7 ibuprofens sold in Korea in 2013 were examined by chiral HPLC. The Chiralcel OD-H column and LUX-Cellulose-1 column were used as chiral stationary phases and the mixed eluent of hexane:isopropanol:acetic acid as 100:1:0.1 was used as a mobile phase with a flow rate of 1.0 mL/min. Each data was obtained from an average value of at least three different experiments for each sample and the average value of relative standard deviation of them appeared very small, 0.19%. Average optical purity value (97.5%) of eleven commercial dexibuprofens used in this study were smaller than those of 9 years ago (99.2%), but larger than four years ago (95.6%). Enantiomeric ratios of (R)- and (S)-isomers of seven ibuprofen samples used in this experiment were achieved at about 50:50 which was different with the result (44:56) from four years ago.

• Journal of the Korean Chemical Society
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• v.36 no.6
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• pp.879-888
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• 1992

Separation of the optical isomers of free amino acids by a reversed phase high performance liquid chromatography has been studied by adding a copper(II) complex of L-proline or L-proline derivatives (hydroxy-L-proline, N-benzyl-L-proline, p-xylenyl-L-proline, p-xylenyl-hydroxy-L-proline) in the mobile phase. An OPA postcolumn detection system was used for the detection of amino acids. The chromatographic properties for the free amino acids were discussed in terms of the pH, the kinds and concentration of chelate or organic modifier. The retention behaviors of the free amino acids were considerably different from, those of DNS-amino acids or DABS-amino acids. The enantioselectivity of the free amino acids was better than that of derivatized amino acids. The enantioselectivity between the optical isomers observed by use of the Cu(II)-p-xylenyl-L-proline chiral cheleate was the best among the several copper(II) chelate. A separation mechanism could be illustrated not only by the hydrophobic interaction of the diastereomer with stationary phase but also by the steric effect of the ligand exchange reaction between the free-amino acids and copper chelate.