• Title/Summary/Keyword: stereochemistry

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The Structure and Stereochemistry of Phytolaccagenic Acid

  • Woo, Won-Sick;Kang, Sam-Sik
    • YAKHAK HOEJI
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    • v.18 no.4
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    • pp.231-235
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    • 1974
  • The structure and stereochemistry of phytolaccagenic acid, a new triterpenoid sapogenin from Phytolacca americana L.has been further characterized as 3${\beta}$23-dihydroxy-30-carbomethoxy-olean-12-en-28-oic acid (I).

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Mitochondrial Affinity of Guanidine-rich Molecular Transporters Built on Monosaccharide Scaffolds: Stereochemistry and Lipophilicity

  • Lee, Woo-Sirl;Kim, Wan-Il;Kim, Kyong-Tai;Chung, Sung-Kee
    • Bulletin of the Korean Chemical Society
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    • v.32 no.7
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    • pp.2286-2300
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    • 2011
  • We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.

Inhibition of Carboxypeptidase A with$\beta$-Lactone-bearing phenylalanine. Design, Synthesis, and Stereochemistry-dependent Inhibition Mode

  • Lee, Mi Jun
    • Bulletin of the Korean Chemical Society
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    • v.22 no.11
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    • pp.1236-1242
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    • 2001
  • (3S,1'S)-3-(1'-Carboxy-2'-phenyl)ethylamino-2-oxetanone (1a) and (3R,1'S)-3-(1'-carboxy-2'-phenyl)ethylamino-2-oxetanone (1b) were designed, synthesized, and evaluated as inhibitors for carboxypeptidase A, a prototypical zinc protease that removes the C-terminal amino acid having an aromatic side chain from oligopeptide substrate. It was concluded from the analysis of inhibition kinetics that while 1a inactivates CPA irreversibly, its diastereoisomer, 1b is a weak competitive inhibitor for CPA. A possible explanation for the observed difference in inhibition mode that is dependent on the inhibitor stereochemistry is offered.

Structural Determination of cis- and trans-5-Hydroxymethyl-5-methyl-2-thiono-r-2-ethoxy-1,3,2-dioxaphosphorinane by NMR and X-ray Crystallography: Model Compounds for the Reaction Mechanism Study of Organophosphorus Pesticides

  • Kim, Jeong Han;Toia, Robert F.;Craig, Donald C.
    • Journal of Applied Biological Chemistry
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    • v.43 no.1
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    • pp.37-43
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    • 2000
  • 1,3,2-Dioxaphosphorinanes are suitable compounds for studying the stereochemistry of substitution at phosphorus. Cis- and trans-5-hydroxymethl-5-methyl-2-thiono-2ethoxy-1,3,2-dioxaphosphorinane were prepared, and their structures and stereochemistry unambiguously assigned by NMR and X-ray crystallography with acetoxy and 3,5-dinitrobenzoyloxy derivatives, respectively. Trans isomer gave $^{31}P$ NMR signal at higher field than cis isomer, and the ring proton Spectrum of cis isomer showed characteristic pattern for identifying its geometry. In X-ray crystallography they adopted a chair conformation with the ethoxy groups in the axial positions, and the sulfide groups in the equatorial positions. A flattening of the ring around the phosphorus center was noted, the POC bond angles were about $120^{\circ}$, and the C-O bonds in the ring were significantly longer than the C-O bond for the ethoxy group or the C-O bond for hydroxyl group.

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Absolute Configuration of ${\beta}$-agarofuran nucleus of euojaponine C by CD exciton chirality method

  • Ryu, Jae-Ha;Ryu, Shi-Yong;Han, Yong-Nam;Han, Byung-Hoon
    • Archives of Pharmacal Research
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    • v.20 no.1
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    • pp.76-79
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    • 1997
  • A new celastraceae alkaloid, euojaponine C has been isolated from the methanol extract of the root bark of Euonymus japonica. With the relative stereochemistry of euojaponine C established by NOESY data, the absolute stereochemistry has been determined by circular dichroism (CD) exciton chirality method. The CD of the 2, 5-bis-phenyl benzoate of triacetonide derived from the LiAlH$_{4}$, hydrolysate, euonyminol shows that the configuration of C-2 and C-5 are both R.

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A new sesterterpenoid showing anti-inflammatory effect from the Marine Sponge Haliclona species

  • Lee, Kyung;Rho, Jung-Rae
    • Journal of the Korean Magnetic Resonance Society
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    • v.19 no.1
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    • pp.23-28
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    • 2015
  • Four spiroketal sestertepenoids (1 ~ 4) were isolated from the marine sponge Haliclona species. Their planar structures were completely determined from a combination of extensive 1D and 2D NMR experiments, and also the relative stereochemistry on the chiral centers were established by the ROESY experiment. Compounds 1 ~ 3 were determined as the same planar structures with different stereochemistry on the chiral centers C-11 and C-13. Of these, 1 was identified as a new stereoisomer. Four compounds showed the inhibition effect of nitric oxide (NO) production in LPS-stimulated RAW 264.7 cells (0.7~2.0 g/ml).