• Title/Summary/Keyword: Stereochemistry

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Synthesis and Antiviral Activity of $2^1$-Fluorohexopyranosyl Nucleosides

  • Jeong, Lak-Shin;Lee, Jong-Eun;Kim, Hea-Ok;Chun, Moon-Woo
    • Archives of Pharmacal Research
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    • v.21 no.3
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    • pp.338-343
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    • 1998
  • $2^1$-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-posiition of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.

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Complete assignments of $^{1}H$ and $^{13}C NMR$ spectra of Chivosazole F

  • Park, Jung-Rae;Jongheonn Shin;Kim, Jin-Cheol;Ahn, Jong-Woong
    • Journal of the Korean Magnetic Resonance Society
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    • v.5 no.2
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    • pp.91-98
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    • 2001
  • The $^1$H and $^{13}$ C NMR spectra of chivosazole F from Sorangium cellulosum were completely assigned by a combination of ID and 2D NMR techniques. The configurations of double bonds were confirmed from the ROESY spectra. The stereochemistry at asymmetric carboncenters was partially assigned on the basis of the results of NOE analysis.

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Two New Scalaranes from a Korean Marine Sponge Spongia sp.

  • Yang, Inho;Nam, Sang-Jip;Kang, Heonjoong
    • Natural Product Sciences
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    • v.21 no.4
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    • pp.289-292
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    • 2015
  • Intensive chemical investigation of Korean marine sponge Spongia sp. has led to the isolation of two new scalaranes. The planar structures of the new compounds 1 and 2 were determined through 1D and 2D NMR spectral data analysis, while the relative stereochemistry of the compounds was determined based on the analysis of $^1H-^1H$ coupling constants and NOESY spectroscopic data. Compounds 1 and 2 did not display any significant biological activities on farnesoid X-activated receptor (FXR) in co-transfection assay.

STEREOCHEMISTRY IN LONG-CHAIN BIRADICAL CYCLIZATION

  • Hasegawa, Tadashi;Yamazaki, Yuko;Yoshioka, Michikazu
    • Journal of Photoscience
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    • v.4 no.1
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    • pp.7-10
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    • 1997
  • The structures of 8-membered azalactone isomers produced from photocyclization of 2-(N,N-dibenzylamino)ethyl benzoylacetate were determined by the X-ray structure analysis to clarify the stereochemical behavior of a 1,8-biradical. The remarkable stereoselectivity in cyclization of the 1,8-biradical to form cis- and trans-isomers of the azalactone was not observed. The ring conformations were boat-chair like and dihedral angles between C$_5$- and C$_6$- phenyl groups were ca 45$\circ$ in the both isomers. The 1,8-biradicals in the transition state for the cyclization would have nearly same boat-chair like conformation and twisted configuration with the dihedral angle of ca 45$\circ$ as the corresponding isomer, and this is responsible for luck of stereoselectivity in long-chain biradical cyclization.

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Structures and Biological Activities of Novel Antibiotic Peptaibols Neoatroviridins A-D from Trichoderma atroviride F80317

  • OH SEUNG UK;YUN BONG SIK;LEE SANG JUN;YOO ICK DONG
    • Journal of Microbiology and Biotechnology
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    • v.15 no.2
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    • pp.384-387
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    • 2005
  • Four new antibiotic peptaibols, named neoatroviridins A (1), B (2), C (3), and D (4), have been isolated from the culture broth of Trichoderma atroviride. Their amino acid sequences were determined mainly by mass spectrometry in combination with NMR studies. The absolute stereochemistry of neoatroviridins was established as L by GC analysis of their acid hydrolysates with derivatization, except for isovaline which was in D. Neoatroviridins, composed of 18 amino acid residues, showed significant membrane-perturbing activity responsible for their antibiotic action, which was comparable to that of alamethicin, a well-known 20-residue peptaibol.

A Density Functional Study on the Addition Effect of 1,2-DACH on the Stereoregularity of PAN in the Polymerization of AN (아크릴로니트릴의 중합시 1,2-DACH의 첨가가 PAN의 입체규칙성에 미치는 영향에 관한 DFT 연구)

  • Cho, Eun-Kyung;Park, Chong-Rae
    • Proceedings of the Korean Fiber Society Conference
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    • 2003.10b
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    • pp.177-178
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    • 2003
  • Many researchers have made efforts to control the stereoregularity in radical polymerization of vinyl monomers because the physical and chemical properties of the polymer are significantly affected by the stereostructure.[1]-[4] In general, monomer design, reaction conditions(e.g. solvent, temperature, and monomer concentration), and additives can alter the stereochemistry of the radical polymerization of acrylic monomer. (omitted)

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Regulation of Stereoselectivity and Reactivity in the Inter- and Intramolecular Allylic Transfer Reactions

  • Yu, Chan-Mo;Youn, Jin-soup;Jung, Hee-Keum
    • Bulletin of the Korean Chemical Society
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    • v.27 no.4
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    • pp.463-472
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    • 2006
  • The preparation of enatiomerically enriched homoallylic alcohols through asymmetric addition of chiral allylic transfer reagents and allylating reagents with chiral catalysts to the carbonyl functionalities represents an important chemical transformation. Excellent progress has been made over past decade in the development and application of catalytic asymmetric allylic transfer reactions. In this account, our efforts for the various intermolecular allylic transfer reactions such as allylation, propargylation, allenylation, and dienylation utilizing accelerating strategy and sequential allylic transfer reactions to achieve multiple stereoselection mainly using transition metal catalysts are described.

Absolute Configurations of (±)-Glabridin Enantiomers

  • Kim, Mi-Hyang;Kim, Soo-Un;Kim, Yong-Ung;Han, Jae-Hong
    • Bulletin of the Korean Chemical Society
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    • v.30 no.2
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    • pp.415-418
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    • 2009
  • Concerned with ambiguous stereochemistry assignment of natural (+)-glabridin, absolute configurations of (${\pm}$)-glabridin enantiomers were studied with synthetic glabridin. Synthetic glabridin enantiomers were separated by semi-preparative Sumi-chiral column chromatography, and characterized by UV-Vis and NMR spectroscopy. Three-dimensional molecular structure of glabridin was obtained as equatorial Ph-3 half chair chroman ring from semi-empirical PM3 calculation, and refined by coupling constants in $^1H$ NMR spectrum. Finally, absolute configurations of two enantiomers were determined by circular dichroism spectroscopy based on the empirical helicity rules. Absolute configuration of natural (+)-glabridin was confirmed as (R)-glabridin, as known.

Effect of the Addition of 1,2-Diaminocyclohexane with Different Configuration on the Polymerization Kinetics and Stereoregularity of Polyacrylonitrile(PAN) (다른 configuration을 가진 1,2-diaminocyclohexane이 폴리아크릴로니트릴(PAN)의 중합 거동과 입체규칙성에 미치는 영향)

  • Bae, Dong-Jin;Park, Chong-Rae
    • Proceedings of the Korean Fiber Society Conference
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    • 2001.10a
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    • pp.101-102
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    • 2001
  • The control of the stereochemistry during the radical polymerization of vinyl monomer has been a long standing concern and is still one of the most important topic in synthetic polymer chemistry.[1-5] The stereoregularity of vinyl polymers often has significant effect on the properties of polymer materials. Therefore, it is important to devise methods to control stereoregularity during the polymerization reactions. (omitted)

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Structural Analogues of Cumambrin B from the Flower of Chrysanthemum boreale

  • Jang, Dae-Sik;Yang, Min-Suk;Ha, Tae-Jung;Park, Ki-Hun
    • Archives of Pharmacal Research
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    • v.21 no.5
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    • pp.591-594
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    • 1998
  • The structural analogues of cumambrin B(1, 2, 3, 4) were isolated from the flower of Chrysnathemum boreale Makino. The structures of compounds were determined by two-dimensional $^{1}H-^{1}H$ COSY and $^{13}C-^{1}H$ COSY spectra with the aid of homonuclear and heteronuclear double resonance experiment. The stereochemistry of compounds has been verified from single crystal X-ray diffraction of cumambrin A(2). the antimicrobial activities of these guaianolides have been studied.

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