• Title/Summary/Keyword: $^1$H-NMR spectra

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Enzymatic Synthesis of Maltol-$\alpha$-Glucoside and Ethyl Maltol-$\alpha$-Glucoside (Maltol-$\alpha$-Glucoside 및 Ethyl Maltol-$\alpha$-Glucoside의 효소적 합성)

  • 김삼곤;김근수;김영회
    • Journal of the Korean Society of Tobacco Science
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    • v.24 no.2
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    • pp.94-100
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    • 2002
  • Cyclodextrin glucanotransferase from Bacillus stearothemophilus and Bacillus macerans synthesized maltol and ethyl maltol monoglucoside, with a series of its maltooligo-glucosides by transglycosylation with dextrin as a donor, and maltol or ethyl maltol as an acceptor. The monoglucoside formed from reaction mixture of maltol or ethyl maltol by the successive actions of Bacillus stearothemophilus cyclodextrin glucanotransferase and Rhizopus glucoamylase was isolated by Diaion HP-20 column and silica gel column chromatography. The structure of the isolated monoglucoside was identified as maltol-$\alpha$-D-glucoside and ethyl maltol-$\alpha$-D-glucoside, respectively, by FAB-MS, UV, $^1$H-NMR, $^{13}$ C-NMR spectra and products by hydrolysis with acid, $\alpha$ - and $\beta$ -glucosidases.

Effects of Axial Ligand Basicity on the Isotropic NMR Shifts in Pyridine-Type Ligands Coordinated to the Paramagnetic Polyoxometalate, $[SiW_{11}Co^{11}O_{39}]^{6-}$

  • 김지영;박석민;소현수
    • Bulletin of the Korean Chemical Society
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    • v.18 no.4
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    • pp.369-373
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    • 1997
  • When 1H NMR spectra of pyridine, 4-amino-, 4-methyl-, and 4-cyanopyridine coordinated to the paramagnetic polyoxometalate, [SiW11CoⅡO39]6- in D2O are compared, both α- and β-proton peaks are shifted upfield as the basicity of the ligand decreases. The isotropic shifts are separated into contact and pseudocontact contributions by assuming that the contact shifts are proportional to the isotropic shifts of the same ligands coordinated to [SiW11NiⅡO39]6-. This separation reveals that the shift variations with the axial ligand basicity are dominated by changes in the magnetic anisotropy (pseudocontact shift) of [SiW11CoⅡ(ptl)O39]6- (ptl=pyridine-type ligand). The magnitude of the magnetic anisotropy in a series of pyridine-type ligands increases linearly as the pKa of their conjugate acids decreases.

Synthesis and Characterization of Low Viscosity Aromatic Hyperbranched Polyester Epoxy Resin

  • Zhang, Daohong;Jia, Demin;Zhou, Zihu
    • Macromolecular Research
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    • v.17 no.5
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    • pp.289-295
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    • 2009
  • Low viscosity aromatic hyperbranched polyester epoxy resin (HTBE) was synthesized by the reaction between epichlorohydrin (ECH) and carboxyl-end hyperbranched polyester (HTB) which was prepared from inexpensive materials $A_2$ (1,4-butanediol glycol, BEG) and $B_3$ (trimellitic anhydride, TMA) by pseudo one-step method. The molar mass of the HTB was calculated from its acid value by "Recursive Probability Approach". The degree of branching (DB) of the HTB was characterized by model compounds and $^1H$ NMR-minus spectrum technology, and the DB of the HTB was about $0.47{\sim}0.63$. The viscosity and epoxy equivalent weight of the HTBE were $3,600{\sim}5,000\;cp$ and lower than 540 g/mol respectively. The reaction mechanism and structure of the $AB_2$ monomer, HTB and HTBE were investigated by MS, $^1H$ NMR and FTIR spectra technology. The molecular size of HTBE is under 8.65 nm and its shape is ellipsoid-like as determined by molecular simulation.

Inhibitory Activity against Helicobacter pylori of Isolated Compounds from Pinus koraiensis Siebold et Zucc Leaves

  • Jo, Bun-Sung;Cho, Young-Je
    • Journal of Applied Biological Chemistry
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    • v.59 no.1
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    • pp.19-23
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    • 2016
  • A phenol substance was extracted from Pinus koraiensis Siebold et Zucc leaf extracts and its biological efficacy was measured. The highest content of the phenol substance contained in Pinus koraiensis Siebold et Zucc leaves was 13.5 mg/g, which was obtained when it was extracted with 80% ethanol. At a concentration of 200 mg/mL, the phenolic substances extracted with 80% ethanol and water showed antimicrobial activities against Helicobacter pylori, producing clear zones of 10 and 12 mm diameter, respectively. Pinus koraiensis Siebold et Zucc. leaf extracts were separated using a Sephadex LH-20 column and 4 fractions were obtained (fractions A-D). Fractions C and D showed the greatest inhibitory activity against Helicobacter pylori producing 10.1 and 12.3 mm clear zones, respectively. These two fractions were purified using a Sephadex LH-20 and MCI-gel column ($H_2O{\rightarrow}100%$ ethanol). Purified compounds A and B were identified as syringic acid and compound C was identified as p-coumaric acid based on $^1H$-nuclear magnetic resonance (NMR), $^{13}C$-NMR, and fast atom bombardment mass spectrometry spectra. When two or more purified compounds were mixed, a synergistic effect of anti-Helicobacter pylori activity was evident. This result indicates that extracts of Pinus koraiensis Siebold et Zucc leaves could be considered a functional food because of their high antimicrobial properties.

Synthesis, Characterization, and Electrochemical Behavior of Viologen-Functionalized Poly(Amidoamine) Dendrimers

  • Oh, Mi-Kyung;Bae, Sang-Eun;Yoon, Jung-Hyun;Roberts, Mary F.;Cha, Eun-Hee;J. Lee, Chi-Woo
    • Bulletin of the Korean Chemical Society
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    • v.25 no.5
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    • pp.715-720
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    • 2004
  • Amineterminated, ethylenediamine core polyamidoamine starburst dendrimers of generation 2 (G2), generation 4 (G4) and generation 6 (G6) have been successfully surface-modified via an amide coupling reaction with 4-ethyl, 4'-(3-propionic) bipyridinium cation and the electrochemical behavior of the resulting dendrimers were investigated in aqueous potassium chloride electrolyte solutions. The 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide-mediated reaction resulted in 25-39% end-group functionalization. The water-soluble 4-ethyl, 4'-(3-propylamide) bipyridinium dibromide dendrimers (G2-V2+, G4-V2+ and G6-V2+) were characterized by $^1H$ NMR and UV-Vis spectroscopic methods. The cyclic voltammetric and chronoamperometric experiments were performed to determine the diffusion coefficient and the number of electrons transferred in the process of the first reduction of the viologen-functionalized dendrimers. Adsorption of viologen-functionalized dendrimers at electrode surface was evidenced in the voltammograms. Experimentally determined diffusion coefficients were in good agreement with the values expected from the Stokes-Einstein relation, while the number of electrons transferred concurred with the extent of functionalization determined by $^1H$ NMR and UV-Vis spectra.

Backbone hydrogen bonding interaction of the inactive isoform of type III antifreeze proteins studied by 1H/15N-HSQC spectra

  • Seo-Ree, Choi;Sung Kuk, Kim;Jaewon, Choi;Joon-Hwa, Lee
    • Journal of the Korean Magnetic Resonance Society
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    • v.26 no.4
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    • pp.46-50
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    • 2022
  • Antifreeze proteins (AFPs) bind to the ice crystals and then are able to inhibit the freezing of body fluid at subzero temperatures. Type III AFPs are categorized into three subgroups, QAE1, QAE2, and SP isoforms, based on differences in their isoelectric points. We prepared the QAE2 (AFP11) and SP (AFP6) isoforms of the notched-fin eelpout AFP and their mutant constructs and determined their temperature gradients of amide proton chemical shifts (𝚫δ/𝚫T) using NMR. The nfeAFP11 (QAE2) has the distinct 𝚫δ/𝚫T pattern of the first 310 helix compared to the QAE1 isoforms. The nfeAFP6 (SP) has the deviated 𝚫δ/𝚫T values of many residues, indicating its backbone conformational distortion. The study suggests the distortion in the H-bonding interactions and backbone conformation that is important for TH activities.

The Structure of Phenolic Compounds and Their Antibiotic Activities in Umbilicaria vellea (Umbilicaria vellea 중 페놀성 화합물의 구조 및 항균활성)

  • Min, Tae Jin;Bae, Kang Gyu
    • Journal of the Korean Chemical Society
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    • v.40 no.9
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    • pp.623-629
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    • 1996
  • In order to identify antibiotic substances in the extract of a lichen, Umbilicaria vellea, the extract was chromatographed and two compounds were isolated. Compound I which showed antifungal and antibacterial activities, melted around 129∼132$^{\circ}C$ and showed UV absorption at 217, 265 and 300 nm. It showed a molecular ion at m/z 196. Its molecular formular was confirmed to be $C_{10}H_{12}O_4$ from elemental analysis. From its IR and NMR data it was identified to be ethyl 2,4-dihydroxy-6-methyl benzoate. Compound II melted around 58∼59$^{\circ}C$ and showed UV absorption at 212, 276 and 282 nm. It showed a molecular ion at m/z 124 and molecular formular was confirmed to be $C_7H_8O_2.$ From the analysis of its IR and NMR spectra it was identified to be 5-methyl-1,3-benzenediol.

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Rapid Mapping of Active Site of KSI by Paramagnetic NMR

  • Joe, Yong-Nam;Cha, Hyung-Jin;Lee, Hyeong-Ju;Choi, Kwan-Yong;Lee, Hee-Cheon
    • Bulletin of the Korean Chemical Society
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    • v.33 no.9
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    • pp.2981-2984
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    • 2012
  • Active site mapping has been done for ${\Delta}^5$-3-ketosteroid isomerase (KSI) by analyses of paramagnetic effect on $^1H-^{15}N$ HSQC spectra using 4-hydroxyl-2,2,6,6-tetramethylpiperidinyl-1-oxy (HyTEMPO) and an intermediate analog (equilenin). Our result revealed that residues in hydrophobic cavity of KSI, particularly active site region, mainly experienced a high line-broadening effect of NMR signal with HyTEMPO, while they experienced full recovery of a lineshape upon the addition of equilenin. The mapped region was very similar to the active site of KSI as described by the crystal structure. These observations indicate that a combined use of paramagnetic reagent and substrate (or analog) could rapidly identify the residues in potential active site of KSI, and can be applied to the analysis of both active site and function in unknown protein.

Extractives from Epimedium koreanum Nakai (삼지구엽초(Epimedium koreanum Nakai)의 추출성분)

  • Lee, Tae-Seong;Cho, Jae-Hyun;Hwang, Byung-Ho
    • Journal of Korea Foresty Energy
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    • v.24 no.2
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    • pp.16-23
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    • 2005
  • The air dried of Epimedium koreanum Nakai was extracted with MeOH and its extractives were concentrated with a vacuum evaporator. The extractives were fractionated with a series of n-hexane, chloroform (${CHCl}_3$), butanol (BuOH), ethyl acetate (EtOAc) and water on a separately funnel. Each fraction was freeze dried to give some dark brown powder. The EtOAc and BuOH soluble fractions were chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-n-hexane mixture as eluents. The isolated compounds were tested with a cellulose TLC developed with TBA and 6% acetic acid and then visualized on UV lamp or sprayed with vanillin-HCl-EtOH. The purified compounds were flavonoids and their glycosides, and organic acid as follows : (+)-catechin, icariin, hyperoside, Ikarisoside A and caffeic acid. The structures of each compounds were confirmed by $^1H-NMR,\;^{13}C-NMR$ and Mass spectra. Also, executed qualitative analysis as use GC/MS(Libraries search) about ${CHCl}_3$ soluble compounds of each part.

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A New Streptothricin Family Antibiotic Producing Streptomyces Spp. Snus 8810-111 ; Characterization of The Producing Organisms, Fermentation, Isolation, and Structure Elucidation of Antibioitics

  • Goo, Yang-Mo;Kim, Ok-Yun;Joe, Young-Ae;Lee, Young-Bok;Ju, Jeongho;Kim, Beom-Beom-Tae;Lee, Youn-Young
    • Archives of Pharmacal Research
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    • v.19 no.2
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    • pp.153-159
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    • 1996
  • A new streptothricin family antibiotic producing Streptomyces spp. SNUS 8810-111 was isolated from a soil sample. Study of its morphological and physiological characters indicated that the antibiotic producing organism was a Streptomyces spp. Taxonomical studies suggested that the organism might belong to the genus streptomyces gougeroti. The organism produced antibiotics most in calcium carbonate-tryptic soy broth. The active principles were recovered from the broth with a cation exchange resin and eluted from the resin with HCI. Cellulose column chromatography gave two active principles.$^1H-^1H$ Homo-COSY study on the first compound revealed four structural components. Total hydrolysis of the antibiotic with HCI allowed isolation of $\beta-lysine$. From these data the antibiotic was found to be streptothricin D. The other compound showed one additional signal in the .$^1H$NMR and the $^{13}C$ NMR spectra. The signal was from a methyl group attached to a nitrogen atom. Comparison of the NMR signals with those of streptothricin D suggested that the compound was N-methyl-streptothricin D which was a new compound in the family of streptothricin antibiotics.

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