• Title/Summary/Keyword: imidazole functional

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Molecularly Imprinted Polymers Having Amidine and Imidazole Functional Groups As an Enzyme-Mimetic Catalyst for Ester Hydrolysis

  • Chen, Wen;Han, Dong-Keun;Ahn, Kwang-Duk
    • Macromolecular Research
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    • v.10 no.2
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    • pp.122-126
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    • 2002
  • A molecularly imprinted polymer (MIP) having both amidine and imidazole functional groups in the active site has been prepared using p-nitrophenyl phosphate as a transition state analogue (TSA). The imprinted polymer MIP with amidine and imidazole found to have the highest hydrolysis activity compared with other MIPs with either amidine or imidazole groups only. It is postulated a cooperative effect between amidine and imidazole in the hydrolysis of p-nitrophenyl methyl carbonate (NPMC) as a substrate when both groups were arranged in proximity by molecular imprinting. The rate enhancement of the hydrolysis by MIP was 60 folds over the uncatalyzed solution reaction and two folds compared with the control non-imprinted polymer CPI having both functional groups. The enzyme-mimetic catalytic hydrolysis of p-nitrophenyl acetate by MIP was evaluated in buffer at pH 7.0 with $K_{m}$ of 1.06 mM and $k_{cat}$ of 0.137 $h^{-1}$ . . .

Infrared Spectroscopy of Imidazole Trimer in Helium Nanodroplets: Free NH Stretch Mode

  • Lee, Seul-Ki;Lee, Seung-Jun;Ahn, Ah-Reum;Kim, Yu-Sic;Min, Ah-Reum;Choi, Myong-Yong;Miller, Roger E.
    • Bulletin of the Korean Chemical Society
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    • v.32 no.3
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    • pp.885-888
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    • 2011
  • We report the first vibrational band assignment of imidazole trimer (IMT) solvated in helium nanodroplets. Several congested vibrational bands of imidazole (IM) clusters were obtained in the frequency region of $3513-3515\;cm^{-1}$ and vibrationally resolved due to the extremely low temperature (0.37 K) and very weak solutesolvent interaction environments of helium droplets. The unambiguous free NH band assignment was achieved with an aid of pick-up oven temperature dependence and vibrational transition moment angle (VTMA) experiments as well as density functional theory (DFT) calculations. The band at $3514.3\;cm^{-1}$ is attributed to the free NH stretching mode of linear IMT clusters, easily formed by the dipole-dipole interactions of IM in ultracold helium nanodroplets.

Synthesis of POSS-Functionalized Imidazole

  • Choi, Kyung-Min;Jang, Hee-Jae;Shin, Dong-Soo
    • Journal of the Korean Chemical Society
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    • v.63 no.1
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    • pp.51-55
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    • 2019
  • The synthesis of N-substituted POSS-imidazole in one pot typically prepared using the condensation method from diketone and aminopropylisobutyl-POSS. A wide variety of functional groups and substitution patterns were tolerated under the present procedure. The resulting compounds can be used as valuable products allowing for the elaboration to OLED, DSSC building block.

Adhesion Properties between Polyimide Film and Copper by Ion Beam Treatment and Imidazole-Silane Compound (이온빔 및 이미다졸-실란 화합물에 의한 폴리이미드 필름과 구리의 접착 특성)

  • Kang, Hyung Dae;Kim, Hwa Jin;Lee, Jae Heung;Suh, Dong Hack;Hong, Young Taik
    • Journal of Adhesion and Interface
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    • v.8 no.1
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    • pp.15-27
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    • 2007
  • Polyimide (PI) surface modification was carried out by ion-beam treatment and silane-imidazole coupling agent to improve the adhesion between polyimide film and copper. Silane-imidazole coupling agent contains imidazole functional groups for the formation of a complex with copper metal through a coordination bonding and methoxy silane groups for the formation of siloxane polymers. The PI film surface was first treated by argon (Ar)/oxygen ($O_2$) ion-beam, followed by dipping it into a modified silane-imidazole coupling agent solution. The results of X-ray photoelectron spectroscopy (XPS) spectra revealed that the $Ar/O_2$ plasma treatment formed oxygen functional groups such as hydroxyl and carbonyl groups on the polyimide film surface and confirmed that the PI surface was modified by a coupling reaction with imidazole-silane coupling agent. Adhesion between copper and the treated PI film by ion-beam and coupling agent was superior to that with untreated PI film. In addition, adhesion of PI film treated by an $Ar/O_2$ plasma to copper was better than that of PI film treated by a coupling agent. The peeled-off layers from the copper-PI film joint were completely different in chemical composition each other. The layer of PI film side showed similar C1s, N1s, O1s spectra to the original Upilex-S and no Si and Cu atoms appeared. On the other hand the layer of copper side showed different C1s and N1s spectra from the original PI film and many Si and Cu atoms appeared. This indicates that the failure occurs at an interface between the imidazole-silane and PI film layers rather than within the PI layers.

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Acid and Base Catalyzed Intramolecular Cyclizations of N-Benzoylthiocarbamoyl-acetals

  • Lee, Bong-Yong;Kim, Choong-Sup;Lee, Jong-Wook
    • Archives of Pharmacal Research
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    • v.23 no.2
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    • pp.99-103
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    • 2000
  • Acid and base catalyzed intramolecular cyclizations of N-benzoylthioureidoacetal, contain-ing four functional groups adjacent to thiourea such as benzocarbamoyl, acetal, thioure and amide, were investigated. The condensation reaction of N-benzoyl thiocarbamoylgly-cine amide in the presence of 10% aqueous NaOH provided 1-(2,2-dimethoxy)ethyl-imi- dazolidine-2-thione exclusively. In the presence of pyridine, it was transformed to 2- thiohydantoin. N-Benzoyl thiocarbamoyl glycine amide was completely transformed to an iminothiazolidine exclusively in the presence of Lewis acid such as borontrifluoride ether-ate or trimethylsilyl iodide. 1-(2,2-Dimethoxy)ethyl-imidazolidine-2-thione was transformed to imidazole[2,1-b]thiazole and pyrazino[5,1-a]imidazole in the presence of $BF_3$.$ET_2$O and formic acid, respectively.

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A Study on the Hydrolysis of p-Nitrophenyl Carboxylates by Micellar Surfactants Catalysts Involving Histidyl Residue (히스티딜기등을 포함하는 미셀성 계면활성제를 촉매로 사용한 파라니트로페닐 에스테르의 가수분해반응에 관한 연구)

  • Won Fae Koo;Choon Pyo Hong
    • Journal of the Korean Chemical Society
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    • v.33 no.1
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    • pp.3-10
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    • 1989
  • In order to obtain a clue in understanding enzymatic hydrolysis in which the His-Cys moieties of papain protease is involved, we prepared cationic peptide-sufactants bearing histidyl, cysteinyl, and both histydyl and cysteinyl residues. Their catalytic efficiency toward the hydrolysis of PNPL were investigated in comicellar phases formed with $N^{+}C_{2}CysC_{12}$, $N^{+}C_{2}HisC_{12}$, $N^{+}C_{2}HisCysC_{12}$ increased markedly in the same order compared with that of $N^{+}C_{2}AlaC_{12}$. The markedly increased catalytic effects are attributed to the imidazole groups of $N^{+}C_{2}HisC_{12}$ and the thiol groups of $N^{+}C_{2}CysC_{12}$, and the large catalytic efficiency of $N^{+}C_{2}HisCysC_{12}$, is considered due to the interaction of the imidazole and the thiol groups. In order to investigate catalytic activities, rate constants for the functional groups, km* and dissociation constants, pKa have been determined. The results showed that $k^{\ast}_m$ and pKa of the imidazole groups were $7.91{\times}10^{-4}S^{-1}$ and 6.49, and those of the thiol groups were $6.00{\times}10^{-4}S^{-1}$ and 10.50. The catalytic effects of comicellar systems on the hydrolysis of p-nitrophenyl esters has increased according to the increasing size of the alkyl carbon number. Therefore, the catalytic effects have been increasing by the interaction of micellar hydrophobic parts and substrates as well as action of the functional groups.

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Histidine (His83) is Essential for Heat Shock Factor 1 (HSF1) Activation in Protecting against Acid pH Stress

  • Lu, Ming;Chang, Ziwei;Park, Jang-Su
    • Bulletin of the Korean Chemical Society
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    • v.34 no.11
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    • pp.3405-3409
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    • 2013
  • The activation of heat shock factor 1 (HSF1) can be induced by the changes in environmental pH, but the mechanism of HSF1 activation by acidification is not completely understood. This paper reports that a low pH (pH~6.0) can trigger human HSF1 activation. Considering the involvement of the imidazole group of histidine residues under acid pH stress, an in vitro EMSA experiment, Trp-fluorescence spectroscopy, and protein structural analysis showed that the residue, His83, is the essential for pH-dependent human HSF1-activation. To determine the roles of His83 in the HSF1-mediated stress response affecting the cellular acid resistance, mouse embryo fibroblasts with normal wild-type or mutant mouse HSF1 expression were preconditioned by heating or pH stress. The results suggest that His83 is essential for HSF1 activation or the HSF1-mediated transcription of heat shock proteins, in protecting cells from acid pH stress.

Extracion and Photoluminescence Properties of Marine Microalgae for Organic Light Emitting Diode Applications (유기발광소자를 위한 해양 미세조류 유래 물질 및 광 발광 탐색)

  • Jung, Sang-Mok;Lee, Han-Seong;Kang, Seul-Gi;Lee, Han-Joo;Son, Ji-Su;Jeon, Jae-Hyuk;Chae, Hee-Baik;Shin, Hyun-Woung
    • Korean Journal of Environment and Ecology
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    • v.29 no.4
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    • pp.564-569
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    • 2015
  • In order to discover materials that can be used for OLED, extractions of marine microalgae was screened for photoluminescence(PL) properties and analyzed using gas chromatography-mass spectrometry(GC-MS). The extractions of Nitzschia denticula, Navicula cancellata and Nannochloropsis salina showed PL spectroscopy among fourteen marine microalgae species. The selected three fractions from three microalgae were analyzed by GC-MS. According to the results, it was found that the identified organic light-emitting materials can be subdivided into three functional groups based on imidazole, purine and quinoline. These chemicals are considered to have a strong relationship with PL spectroscopy for OLED materials.

Application of Excited-State Intramolecular Proton Transfer (ESIPT) Principle to Functional Polymeric Materials

  • Park, Sang-Hyuk;Kim, Se-Hoon;Seo, Jang-Won;Park, Soo-Young
    • Macromolecular Research
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    • v.16 no.5
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    • pp.385-395
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    • 2008
  • Synthesis and properties of novel excited-state intramolecular proton transfer (ESIPT) materials, recently developed in our group, are described. Highly efficient ESIPT reaction, achieved in polyquinolines, polybenzoxazoles, and oxadiazole and imidazole derivatives possessing an intramolecular tautomerizable hydrogen bond, has been investigated theoretically and experimentally. It is demonstrated that unique properties arising from the ESIPT process (large Stokes' shift, no self-absorption, and easy population inversion, etc.) make it possible to produce advanced polymer devices for lasing, optical storage, and electroluminescence.

Synthesis of substituted urea or benzimidazolone using 1,1'- carbonyldiimidazole and substituted anilines

  • Kyounghoon Lee
    • Journal of the Korean Magnetic Resonance Society
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    • v.28 no.3
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    • pp.15-19
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    • 2024
  • 1,1'-carbonyldiimidazole (CDI) is a versatile reagent that can be used for synthesizing a variety of organic compounds containing carbonyl functional groups. The reactivity of CDI with two ortho-substituted anilines was tested and characterized with analytic techniques such as NMR, IR, and ESIMS. A reaction of CDI with two equivalents of disubstituted aniline (N1,N1-diethylbenzene-1,2-diamine) formed a urea compound, 1,3-bis(2-(diethylamino)phenyl)urea (1). On the other hand, a reaction with one equivalent of mono-substituted aniline (tert-butyl (2-aminophenyl)carbamate) formed a substituted benzimidazolone, tert-butyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate (2). These results demonstrated that a singly substituted aniline prefers an intramolecular ring formation while an N,N-doubly-substituted aniline prefers a urea formation.