• Title/Summary/Keyword: Carboxylic Acids

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Convenient Procedure for the Reduction of Carboxylic Acids via Acyloxyborohydrides

  • Cho, Byung-Tae;Yoon, Nung-Min
    • Bulletin of the Korean Chemical Society
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    • v.3 no.4
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    • pp.149-152
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    • 1982
  • A new convenient method for the reduction of carboxylic acids to the corresponding alcohols via acyloxyborohydrides was explored. Acyloxyborohydrides, prepared from the reaction of various carboxylic acids and sodium borohydride, underwent reduction to the corresponding alcohols readily by the addition of dimethyl sulfate or Lewis acids, such as boron trifluoride etherate and triphenyl borate, presumably through acyloxyboranes. By utilizing this procedure, aliphatic and aromatic acids are rapidly and quantitatively reduced to the corresponding alcohols in terahydrofuran either at room temperature (or at $65^{\circ}$). This procedure provides selective reduction of carboxylic acids in the presence of halogen, nitro, and heterocyclic rings such as furan and thiophene.

Cyclic Oligopyrroles as Sensors for Absolute Configuration Determination of Carboxylic Acids

  • Lintuluoto Juha M.;Nakayama Kana;Setsune Jun-Ichiro
    • Proceedings of the Polymer Society of Korea Conference
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    • 2006.10a
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    • pp.241-241
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    • 2006
  • Absolute configuration of carboxylic acids, including amino acids can be determined by circular dichroism (CD) exciton chirality method. This method employs cyclic oligopyrroles able to form stable complexes with carboxylic acids. Addition of carboxylic acids to the oligopyrroles induce CD spectrum at the macrocycle absorption region and in which the sign of the $1^{st}$ Cotton effect is determined solely by the absolute configuration of the carboxylic acid. The basicity of the pyrrole nitrogen can be controlled by macrocycle substitution thus yielding more sensitive chirality sensors.

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Effect of Carboxylic Acid on the Hydration of Plaster of Paris under Alkalinity (알카리성 분위기에서 소석고의 수화에 미치는 카르복실산의 영향)

  • 이승헌
    • Journal of the Korean Ceramic Society
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    • v.31 no.10
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    • pp.1107-1114
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    • 1994
  • Although various theories have been presented on the mechanism of setting retardation of plaster in addition to organic admixtures. The purpose of this paper is that Hydration studies of plaster of paris in the presence of carboxylic acids under alkalinity are examined in the coordination chemistry. Setting of plaster of paris is retarded by the addition of carboxylic acids except oxalic acid. And setting of plaster of paris contained 5 wt% of Ca(OH)2 is also retarded by the addition of above-mentioned carboxylic acids. The degree of retarding effect under alkalinity is found to be a function of the number of the functional group and the length of carbon chain of carboxyl acids. These reasons are attributed to the soluble complex formation, that is calcium complex formation between calcium ion and carboxylic acids. The author's proposal was confirmed by the results of electrical conductivity measurement. The formation of calcium complex was surpported by IR spectra.

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Competitive Inhibition of Pepsin by Carboxylic Acids (脂肪酸에 依한 Pepsin의 競走的 억제)

  • Hong Dae Shin
    • Journal of the Korean Chemical Society
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    • v.14 no.2
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    • pp.161-168
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    • 1970
  • In order to obtain the more effective evidence, supporting the hypothesis which have been previously described by former report that pepsin (EC 3.4. 4.1) forms a hydrophobic bond with the nonpolar side chain of its substrate, the inhibitory effect of carboxylic acids(from formic acid to iso-butyric acid) on the activity of pepsin to the synthetic dipeptide, N-Carbobenzoxy-L-glutamyl-L-tyrosine, was discussed. The kinetic study showed that the inhibition by carboxylic acids was competitive. The Kidecreased with increasing size of the inhibitor molecule. The $-{\Delta}F^{\circ}$increased linearly with increasing number of carbon atoms in the hydrocarbon chain of the inhibitor. It was confirmed that the hydrophobic bond between more than one side chain of amino acid residues(phenylalanine) in the binding region of the active center of pepsin and the side chain of amino acid residues in the substrate was formed as the first step of its enzymic mechanism. The inhibitory effect of carboxylic acids was due to the competition of the hydrocarbon group of the carboxylic acids with the side chain of the substrate for the hydrophobic binding site(the side chain of phenylalanine) of the pepsin.

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Morphology of Metal Salt of Carboxylic Acid: Metal and Acid Dependency on Branched Round Cluster Images

  • Min Su Kang;Kwang-Jin Hwang
    • Journal of the Korean Chemical Society
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    • v.67 no.4
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    • pp.222-225
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    • 2023
  • Metallic salts of C10-18 aliphatic carboxylic acids were prepared and their scanning electron microscopic images were analyzed for the morphology dependency with the metal and the carboxylic acid. Regardless of metal ion, metal salts of dicarboxylic acids showed a high crystallinity with a fiber image (SuA-Na). The aromatic dicarboxylates also represented a morphology of a rectangular-rod or board shapes (IA-Li, IA-Ba). With Na ion, most aliphatic carboxylate (MA, PA, SA) showed a fiber-like crystallinity. However, other monovalent Li, K and multivalent Mg, especially Al ion resulted a glassy-amorphous in the metallic salts of acids (MA, PA, SA). With divalent Ba and Ca ions, the metal salt of aliphatic acids expressed a branched round cluster shape as in SA-Ca, SA-Ba. Both Li and Mg ions with a similar size showed a strong morphological similarity in the metallic salts of aliphatic acids MA, PA, SA. In the case of Na and Ca ions with a similar size (98, 106 pm), both ionic salts of stearic acid gave a branching effect for a fiber or round granular image. In the case of hydroxyl-aliphatic acids (HLA, HPA, HSA), the fiber images in HLA-Na and HSA-Na was appeared about 100 nm thicker than those of nonhydroxycarboxylates (LA-Na, SA-Na). The metallic salts of unsaturated C-18 carboxylic acids (OlA, LeA and LnA) showed an amorphous glassy image due to a kinked carbon chain.

Regulation of 3-Deoxy-D-arabinoheptulosonate-7-phosphate (DAHP) Synthase of Bacillus sp. B-6 Producing Phenazine-1-carboxylic acid

  • Kim, Kyoung-Ja
    • BMB Reports
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    • v.34 no.4
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    • pp.299-304
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    • 2001
  • The 3-Deoxy-D-arabinoheptulosonate 7-phosphate (DAHP) synthase is the first enzyme of aromatic amino acid-, folic acid-, and phenazine-1-carboxylic acid biosynthetic pathways. DAHP synthase of Bacillus sp. B-6 that produces phenazine-1-carboxylic acid was feedback inhibited by two intermediary metabolites of aromatic amino acid biosynthetic pathways, prephenate and chorismate, but not by other metabolites, such as anthranilic acid, shikimic acid, p-aminobenzoic acid, and 3-hydroxyanthranilic acid. DAHP synthase of Bacillus sp. B-6 was not inhibited by end products, such as aromatic amino acids, folic acid, and phenazine-1-carboxylic acid. The inhibition of DAHP synthase by prephenate and chorismate was non-competitive with respect to erythrose 4-phosphate and phosphoenolpyruvate. Prephenate and chorismate inhibited 50% of the DAHP synthase activity at concentrations of $2{\times}10^{-5}\;M$ and $1.2{\times}10^{-4}\;M$, respectively The synthesis of DAHP synthase of Bacillus sp. B-6 was not repressed by exogenous aromatic amino acids, folic acid, and phenazine 1-carboxylic acid, single or in combinations.

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Sensitive and Mild Fluorogenic Reagents for Biogenic Carboxylic Acids in HPLC

  • Ushijima, Tamano;Saito, Mikihiko;Sasamoto, Kazumi;Ohkura, Yosuke;Ueno, Keiyu
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.545-551
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    • 1995
  • Five acid hydrazides as precolumn fluorescence derivatization reagents for carboxylic acids in HPLC, which have the benzofuran or benzothiazole moiety conjugated to a furan, thiophene or oxazoline ring, were synthesized and examined in view of reactivity, separability and sensitivity. Of these hydrazides, 2-(5-hydrazinocarbonyl-2-oxazolyl)-5,6-dimethoxybenzothiazole (BTOH) was most favorable. The detection limit of lauric acid as a model acid was 0.1 pmol per $10-{\mu}l$ injection volume at S/N=3, which was roughly equal to that of an analogous compound, 2-(5-hydrazinocarbonyl-2-furyl)-5,6-dimethoxybenzothiazole. The reagent allowed rapid assays of carboxylic acids ($C_{12:0}-C_{20:4}$) within 20 min with satisfactory scparability. The method was applied to the determination of fatty acids in human sera from healthy volunteers as well as from patients with diabetes or thyroid dysfunction.

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Synergistic extraction of lanthanoids(III) with thenoyltrifluoroacetone and aromatic carboxylic acids and the hydration of the extracted species

  • Ishiwata, E.;Kimura, T.;Kato, Y.;Hasegawa, Y.
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.499-503
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    • 1995
  • In order to study how and why the stabilities of lanthanoid(III) complexes in solutions vary across the series, the formation constants of the adducts of tris(2-thenoyltrifluoroacetonato)lanthanoids(III) with seven carboxylic acids in chloroform have been determined by solvent extraction technique at 298K. The formation constants with carboxylic acids generally decrease with increasing the atomic number, but in the middle of the series, they change only slightly. Such trends have been interpreted as related to a change of the coordination number in the middle of the series. It has been attempted to determine the number of water molecules coordinated to the adducts as well as $Eu(TTA)_3$ in chloroform by measuring the fluorescence life time of europium(III), to ensure the assignment of the coordination number.

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Chemical Modification of the $\beta$-D-Xylosidase from Bacillus stearothermophilus (화학적 수식에 의한 Bacillus stearothermophilus $\beta$-D-Xylosidase 의 연구)

  • 서정한;최용진
    • Microbiology and Biotechnology Letters
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    • v.22 no.6
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    • pp.636-642
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    • 1994
  • Essential amino acids involving in the catalytic mechanism of the $\beta$-D-xylosidase of Bacillus stearothermophilus were determined by chemical modification studies. Among various che- mical modifiers tested N-bromosuccinimide (NBS), $\rho$-hydroxymercurybenzoate (PHMB), N-ethylma- leimide, 1-[3-(di-ethylamino)-propyl]$-3-ethylcarbodi-imide (EDC), and Woodward's Reagent K(WRK)inactivated the enzyme, resulting in the residual activity of less than 20%. WRK reduced the enzyme activity by modifying carboxylic amino acids, and the inactivation reacion proceeded in the form of pseudo-first-order kinetics. The double-lagarithmic plot of the observed pseudo-first- order rate constant against the modifier concentration yielded a reaction order of 2, indicating that two carboxylic amino acids were essential for the enzyme activity. The $\beta$-D-xylosidase was also inactivated by N-ethylmaleimide which specifically modified a cysteine residue with a reaction order of 1, implying that one cysteine residue was important for the enzyme activity. Xylobiose protected the enzyme against inactivation by WRK and N-ethylmaleimide, revealing that carboxylic amino acids and a cysteine residue were present at the substrate-binding site of the enzyme molecule.

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