• Title/Summary/Keyword: Enantiomers

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Catalytic Asymmetric Allylic Alkylation with A Novel P-S Bidentate Ligand

  • Gang, Ja Hyo;Yu, Seong Hun;Kim, Ju In;Jo, Hyeong Geun
    • Bulletin of the Korean Chemical Society
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    • v.16 no.5
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    • pp.439-443
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    • 1995
  • Both enantiomers of (S)-(-)-2-(diphenylphosphino)-2'-mercapto-1,1'-binaphthyl and their derivatives were obtained by synthesis from racemic 2,2'-dihydroxy-1,1'-binaphthyl and subsequent resolution. The utilities of these ligands were investigated briefly. And among these, S-methyl derivative 15 has proved to be an effective ligand for Pd-catalyzed allylic alkylation.

Asymmetric Synthesis of Both Enantiomers of 4-Hexanolide, a Component of the Female Sex Pheromone from the Dermestid Beetle Trogoderma Glabrum

  • Kwang-Youn Ko;E.L. Eliel
    • Bulletin of the Korean Chemical Society
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    • v.10 no.6
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    • pp.559-563
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    • 1989
  • Optically active (R)- and (S)-2-benzyloxy-1-butanol have been prepared by a previously described asymmetric synthesis based on a chiral oxathiane and have been converted into (R)-(+)-4-hexanolide, a component of the pheromone secreted by the female of the dermestid beetle, and its enantiomer.

Liquid Chromatographic Resolution of 2-Hydroxy Acids on Chiral Stationary Phases : A Mechanistic Consideration

  • Myung Ho Hyun;Chung-Sik Min
    • Bulletin of the Korean Chemical Society
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    • v.10 no.6
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    • pp.578-581
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    • 1989
  • Two enantiomers of various 2-hydroxy acid esters have been resolved as the 3,5-dinitrophenyl carbamates on chiral stationary phases (CSPs) derived from ${\alpha}-arylalkylamines.$ Two CSPs, each of which contains the same type of chiral moiety, but shows different mode of connection to a silica support, have been found to show the contrasting resolution behaviors. From the contrasting resolution behaviours of two CSPs used in this study, two competing chiral recognition mechanisms are proposed.

Chiral separation of $\beta$-blockers after derivatizalion wilh a new chiral derivalizalion agen1.GATC and Comparison wilh GITC on derivalizing conditions and chromalographic paramelers

  • Ko, Mi-Young;Shin, Dae-Hong;Seo, Sang-Hun;Kim, Kyeong-Ho
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.398.1-398.1
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    • 2002
  • A new chiral derivatization agent with sugar moiety. 2, 3.4, 6-tetra-O-acetyl-D-galactopyranosyl isothiocyanate (GATC) was synthesized. Several $\beta$-blockers were investigated for the possible separation of the enantiomers by reversed-phase HPLC after derivatization with this new chiral derivatization agent (GATC). GATC was reacted readily with $\beta$-blockers at room temperature and the reaction mixture could directly be injected into the HPLC system. (omitted)

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Enantiomeric Profiling Analysis of NSAIDs by Capillary Electrophoresis Using TM $\beta$-Cyclodextrin as the Chiral Selector

  • Kim, Ji-Young;La, Sookie;Kim, Jung-Han;Kim, Kyoung-Rae
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.400.1-400.1
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    • 2002
  • Because of the differences in pharmacological properties between enantiomers of chiral acidic non-steroidal antiinflammatory drugs (NSAIDs) in human body. accurate determinations of their optical purities have been in great need. An efficient capillary electrophoretic (CE) profiling method was developed for the enantioseparation of NSAIDs. Capillary electrophoretic conditions were optimized using TM$\beta$-cyclodextrin as the chiral selectors under MES buffer. (omitted)

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Chiral separation of $\beta$-agonists after derivatization with a new chiral derivatization agent, GATC

  • Min, Kyeong-Il;Ko, Mi-Young;Kim, Kyeong-Ho
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.275.2-276
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    • 2003
  • Several ${\beta}$-agonists were investigated for the possible separation of the enantiomers by reversed-phase high-performance liquid chromatography after derivatization with a new chiral derivatization agent, GATC. The derivatization proceeded quantitatively within 1 h at room temperature. The corresponding diastereomers were well resolved an ODS column with acetonitrile-acetate buffers a mobile phase and monitored at UV 254nm. (omitted)

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Liquid Chromatographic Resolution of Pyrethroic Acids and Their Esters on Chiral Stationary Phases

  • Lee, Won-Jae;Baek, Chae-Sun;Jing, Yu-Jin
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.224.2-224.2
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    • 2003
  • Pyrethroic acids are essential chiral intermediates of the pyrethroids, which account for about 25% of the world insecticide market and are found to be some of the most effective commercially available pesticides. It was demonstrated that polysaccharide-derived chiral stationary phases (CSPs) are very efficient for the separation of the enantiomers of pyrethroid acids. It was observed that the enantioseparation of pyrethroic methyl ester and ethyl derivatives was well accomplished on brush-type WhelkO-1. (omitted)

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Chiral Separation of Lactic Acid in Culture Media and Cells of Lactobacillus delbrueckii subsp. lactis as O-Pentafluoropropionylated (S)-(+)-3-Methyl-2-Butyl Ester by Achiral Gas Chromatography-Mass Spectrometry

  • Paik, Man-Jeong;Nguyen, Duc-Toan;Yoon, Jae-Hwan;Chae, Han-Seung;Kim, Kyoung-Rae;Lee, Gwang;Lee, Pyung-Cheon
    • Bulletin of the Korean Chemical Society
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    • v.32 no.7
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    • pp.2418-2422
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    • 2011
  • The enantiomeric separation of lactic acid for its absolute configuration has become important task for understanding its biological origin and metabolic process involved in the formation of lactic acid. It involves the conversion of enantiomers as diastereomeric O-pentafluoropropionylated (S)-(+)-3-methyl-2-butyl ester and the direct separation by gas chromatography-mass spectrometry on a achiral capillary column. The (R)- and (S)-lactic acids were completely separated with a high resolution of 1.9. The newly developed method showed good linearity (r ${\geq}$ 0.999), precision (% relative standard deviation = 3.4-6.2), and accuracy (% relative error = -7.7-1.4) with the detection limit of 0.011 ${\mu}g/mL$. When the method was applied to determine the absolute configuration of lactic acid in Lactobacillus delbrueckii subsp. lactis 304 (LAB 304), the composition (%) of (R)-lactic acid in the cell pellet and in the culture medium were $89.0{\pm}0.1$ and $78.2{\pm}0.4$, respectively. Thus, it was verified that the present method is useful for the identification and composition test of lactic enantiomers in microorganisms.

Enantioconvergent Hydrolysis of Racemic Epoxides for Production of Enantiopure Epoxides and Vicinal Diols using Epoxide Hydrolases (에폭사이드 가수분해효소에 의한 광학수렴반응을 이용한 광학활성 에폭사이드 및 Vicinal Diol 제조)

  • Lee, Eun-Yeol
    • KSBB Journal
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    • v.22 no.3
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    • pp.123-128
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    • 2007
  • One drawback of conventional kinetic resolution of racemic epoxides by epoxide hydrolase (EH) is that the theoretical yield can never exceed 50%. This 50% limitation can be overcome by using enantioconvergent process, in which both enantiomers of the racemic epoxide are transformed via stereochemically matching pathways into a single enantiopure diol as the sole product in 100% theoretical yield. In order to make a single enantiopure vicinal diol, the two enantiomers of the racemic epoxide must be hydrolyzed with retention and inversion of configuration each other. The EHs should be enantio- and regiospecific at the same time. The enantioconvergent hydrolysis with EHs and relevant biotransformation for preparing enantiopure epoxides and vicinal diols with a high yield are reviewed.