• Title/Summary/Keyword: stereochemistry

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Studies on the Constituents of Kalopanax Nakai var typicum Nakai (해동피(海桐皮) 성분(成分)에 관(關)한 연구(硏究))

  • Kim, Hack-Seung
    • Journal of Pharmaceutical Investigation
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    • v.4 no.4
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    • pp.5-16
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    • 1974
  • Liriodendrin, m. p. $269-270^{\circ}$, $C_{22}$ $H_{46}$ $O_8$ as one of the antihypertensive components was obtained from the cortex of Kalopanax pictum. Acid hydrolysis of liriodendrin yielided liriresinol-A, -B and glucose. The stereochemistry of liriodendrin was established by the NMR spectrum of liriodrin octaacelate. The NMR spectrum of liriodendrin octaacetate showed that $di-{\beta}-glucoside$ of lirioresinol-B type occurs in nature.

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Photoreaction of 8-Methoxypsoralen with Thymine

  • Shim, Sang-Chul;Kim, Yong-Zu
    • Bulletin of the Korean Chemical Society
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    • v.4 no.2
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    • pp.95-99
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    • 1983
  • Photoreaction of 8-methoxypsoralen (8-MOP) with thymine (${\ge}$ 300 nm) was carried out in the dioxane-water frozen state. One major and two minor monoaddition products between 8-MOP and thymine were isolated by various chromatographic methods. Major monoadduct was characterized to be a C4 cycloaddition product formed between 5,6-double bond of thymine and 3,4-double bond of 8-MOP with cis-anti stereochemistry. Two minor adducts were proved to be stereoisomers of this major adduct.

Synthesis of Perhydroisoquinoline Ring Systems by N-Acyliminium Cyclization$^\sharp$

  • Choi, Joong-Kwon;Jung, Young-Shik;Park, No-Sang
    • Bulletin of the Korean Chemical Society
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    • v.9 no.3
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    • pp.129-132
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    • 1988
  • The stereochemistry of N-acyliminium cyclizations to form decahydropyrrolo[2,1-a]isoquinolin-3(2H)-ones was studied. Particular attention was paid to the stereocontrol by an acetoxy group present on pyrrolidone ring. Two of the three new chiral centers were formed stereospecifically, and the third was controlled by elimination-hydrogenation sequence.

Deoxygenation of ${\beta}$-Aryl-${\alpha}$,${\beta}$-Epoxy Silanes to Vinylsilanes by Magnesium-Magnesium Halide

  • Kang, Kyung-Tae;Park, Chun-Yi;Kim, Joung-Sook
    • Bulletin of the Korean Chemical Society
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    • v.13 no.1
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    • pp.48-53
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    • 1992
  • The reactions of ${\beta}-aryl-{\alpha},{\beta}-epoxy$ silanes with magnesium bromide or magnesium iodide in the presence of excess magnesium in ether at room temperature afforded vinylsilanes in 18-100% yields. E-Vinylsilanes were predominant over Z-isomers (> 80%) regardless of the stereochemistry of ${\alpha},{\beta}-epoxy$ silanes.

Performance of HPLC Chiral Stationary Phases with Two Chiral Units and the Effect of the Stereochemistry of the Second Chiral Unit on the Chiral Recognition

  • 현명호;황승렬;한상철
    • Bulletin of the Korean Chemical Society
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    • v.20 no.11
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    • pp.1309-1312
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    • 1999
  • Two chiral stationary phases (CSPs) derived from two diastereomers consisting of (R)- or(S)-α-naphthylethylamine and (S)-naproxen were found to show different chromatographic behaviors in resolving N-(3,5-dinitrobenzoyl)-α-arylalkylamines and N-(3,5-dinitrobenzoyl)-α- or β-amino amides and esters. From the different chromatographic resolution behaviors on the two CSPs, the chiral recognition is proposed to be controlled mainly by the (R)- or (S)-α-naphthylethylamine part of the CSP. In contrast, the (S)-naproxen part of the two CSPs is proposed to exert some subordinate effects on the chiral recognition.

Isolation of a New Carotenoid Pigment from an Undescribed Gorgonian of the Genus Muricella

  • 노정래;서영완;조기웅;송준임;신종헌
    • Bulletin of the Korean Chemical Society
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    • v.17 no.6
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    • pp.529-531
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    • 1996
  • Muricellaxanthin, a novel carotenoid pigment has been isolated by activity-guided separation from an undescribed gorgonian of the genus Muricella collected from Jaeju Island. Structure of this compound has been determined by a combination of spectral methods. Stereochemistry has been defined by interpretation of nOe data and comparison of CD data with related compounds. Muricellaxanthin exhibited potent lethality against brine-shrimp larvae.

New Cytotoxic Metabolites from a Marine Sponge Homaxinella sp.

  • Mansoor Tayyab A.;Hong, Jong-Ki;Lee, Chong-O;Sim, Chung-Ja;Im, Kwang-Sik;Jung, Jee H.
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.190.3-190.3
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    • 2003
  • Three new butenolides (1-3), and a new cyclopentenone derivative (4) were isolated from a marine sponge Homaxinella sp. by bioactivity guided fractionation. The gross structures were established on the basis of NMR and MS analyses. The stereochemistry of the butenolides and cyclopentenone derivative was defined on the basis of optical rotation and CD spectroscopy. The compounds were tested against a panel of five human solid tumor cell lines and displayed marginal to significant cytotoxicity.

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Enzymatic Formation of Guaiacylglycerol 8-O-4'-(Coniferyl Alcohol) Ether from Coniferyl Alcohol with Enzyme Preparations of Eucommia ulmoides

  • Alam, Md. Shameul;Katayama, Takeshi;Suzuki, Toshisada;Sultana, Deeder;Sultana, Saima;Hossain, Md. Daud
    • Journal of Crop Science and Biotechnology
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    • v.11 no.1
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    • pp.45-50
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    • 2008
  • Lignans and neolignans are optically active plant secondary metabolites. Research on biosynthesis of lignans has already been advanced especially for the formation of (+) pinoresinol but information on the biosynthesis of 8-O-4'- neolignans is still limited. Moreover, the chemical structure(position of substituents on aromatic rings) and stereochemistry of 8-O-4' neolignans is not clear. Katayama and Kado discovered that incubation of cell-free extracts from E. ulmoides with coniferyl alcohol in the presence of hydrogen peroxide gave (+)-erythro- and (-)-threo- guaiacylglycerol 8-O-4'-(coniferyl alcohol) ether (GGCE)(diastereomeric ratio, 3:2) which is the first report on enzymatic formation of optically active -8-O-4' neolignans from an achiral monolignol. In this aspect, enzymatic formation of guaiacyl 8-O-4' neolignan is noteworthy to clarify its stereochemistry from incubation of coniferyl alcohol with enzyme prepared from Eucommia ulmoides. In this experiment, soluble and insoluble enzymes prepared from E. ulmoides were incubated with 30 mM coniferyl alcohol(CA) for 60 min. The enzyme catalyzed GGCE, dehydrodiconiferyl alcohol(DHCA), and pinoresinol identified by reversed phase HPLC. Consequently, diastereomeric compositions of GGCE were determined as erythro and threo isomer. Enantiomeric composition was determined by the chiral column HPLC. Both enzyme preparations enantioselectively formed (-)-erythro, (+)-erythro and (+)-threo, (-)-threo-GGCEs respectively.

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Control of Hydrolytic Degradation of Polylactide Mixtures Using Optical Isomers (광학이성질체를 이용한 폴리락타이드 혼합물의 가수분해성 조절)

  • Lee, Won-Ki
    • Polymer(Korea)
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    • v.36 no.3
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    • pp.309-314
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    • 2012
  • To control degradation rate of biodegradable poly(lactide)s (PLA), the stereochemical PLAs with different ratios of $d$-lactide and $l$-lactide units were synthesized by the ring open polymerization and a degradation behavior was measured by a Langmuir film balance. Degradation rates of mixture monolayers on alkaline subphase were investigated as a function of optical purity of mixture component, 100, 99, 97 and 95%. As increasing their optical purity, melting temperatures of mixtures from stereocomplexation increased. The degradation rate of mixture monolayer with 100% optical purity was much slower than that of each homopolymer one and the others showed 2 step degradation behaviors. In the first step, the degradation which is faster than that of each homopolymer occurs in the uncomplexed region, and secondly, the degradation occurred in the complexed region which showed similar degradation rate to that of 100% optical purity. These results indicate that the alkaline degradation of stereochemical PLAs could be controlled by stereochemistry and stereocomplexation between enantiomer PLAs.