• Title/Summary/Keyword: Biological Synthesis

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Synthesis and Properties of Pyrrolidinium and Piperidinium Bis(trifluoromethanesulfonyl)imide Ionic Liquids with Allyl Substituents

  • Yim, Tae-Eun;Lee, Hyun-Yeong;Kim, Hyo-Jin;Mun, Jun-Young;Kim, Sang-Mi;Oh, Seung-M.;Kim, Young-Gyu
    • Bulletin of the Korean Chemical Society
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    • v.28 no.9
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    • pp.1567-1572
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    • 2007
  • New pyrrolidinium and piperidinium bis(trifluoromethanesulfonyl)imide (TFSI) ionic liquids (ILs) having allyl substituents were synthesized and characterized. All of them are liquid at room temperature and stable up to 300 oC. The pyrrolidinium-based ILs showed better conductivities and lower viscosities than the corresponding piperidinium-based ILs. Among them, 1-allyl-1-methylpyrrolidinium TFSI showed the lowest viscosity of 52 cP, the highest conductivity of 5.7 mS cm?1, and the most negative cathodic voltage window of ?3.2 V (vs. Fc/Fc+) on a platinum electrode, which are the improved results compared to the corresponding analogue having a saturated substituent, 1-methyl-1-propylpyrrolidinium TFSI.

Synthesis and biological activity of 6'-phenylgriseofulvin as analogs of antibiotic griseofulvin (항진균성항생물질 griseofulvin 유도체인 6'-phenylgriseofulvin의 합성과 항균활성)

  • Ko, Byoung-Seob;Oritani, Takayuki;Yamashita, Kyohei
    • Applied Biological Chemistry
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    • v.35 no.5
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    • pp.395-398
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    • 1992
  • In order to study the influence of a 6'-methyl group in ring C of griseofulvin ${\underline{(1)}}$ on the fungicidal activity, 6'-methyl group was replaced with a larger phenyl group as $({\pm})-6'-phenylgriseofulvin$ ${\underline{(3)}}$, $({\pm})-6'-epiphenylgriseofulvin$ ${\underline{(4)}}$, synthesized by a Diels-Alder cycloaddition. Their biological activities were examined against Botrytis allii (IFO 9430) and B. cinerea (AHU 9573). $({\pm})-6'-Phenylgriseofulvin $ ${\underline{(3)}}$ showed high activity in $25\;{\mu}g/disc$.

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Synthesis of Chlorogenic Acid and p-Coumaroyl Shikimates from Glucose Using Engineered Escherichia coli

  • Cha, Mi Na;Kim, Hyeon Jeong;Kim, Bong Gyu;Ahn, Joong-Hoon
    • Journal of Microbiology and Biotechnology
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    • v.24 no.8
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    • pp.1109-1117
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    • 2014
  • Chlorogenic acid and hydroxylcinnamoyl shikimates are major dietary phenolics as well as antioxidants, with recently discovered biological, activities including protection against chemotheraphy side effects and prevention of cardiovascular disease and cancer. Certain fruits and vegetables produce these compounds, although a microbial system can also be utilized for synthesis of chlorogenic acid and hydroxylcinnamoyl shikimates. In this study, we engineered Escherichia coli to produce chlorogenic acid and p-coumaroyl shikimates from glucose. For the synthesis of chlorogenic acid, two E. coli strains were used; one strain for the synthesis of caffeic acid from glucose and the other strain for the synthesis of chlorogenic acid from caffeic acid and quinic acid. The final yield of chlorogenic acid using this approach was approximately 78 mg/l. To synthesize p-coumaroyl shikimates, wild-type E. coli as well as several mutants were tested. Mutant E. coli carrying deletions in three genes (tyrR, pheA, and aroL) produced 236 mg/l of p-coumaroyl shikimates.

Synthesis of LiDAR-reflective Hollow-structured Black Materials and Recycling of Their Etched Waste for Semiconductor Epoxy Molding Compound (라이다 반사형 중공구조 검은색 물질의 개발 및 코어 에칭 폐액 재활용을 통한 반도체용 에폭시 몰딩 컴파운드 응용)

  • Ha-Yeong Kim;Min Jeong Kim;Jiwon Kim;Suk Jekal;Seon-Young Park;Jong Moon Jung;Chang-Min Yoon
    • Journal of the Korea Organic Resources Recycling Association
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    • v.31 no.1
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    • pp.5-14
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    • 2023
  • In this study, LiDAR-reflective black hollow-structured silica/titania(B-HST) materials are successfully synthesized by employing the NaBH4 reduction and etching method on silica/titania core/shell(STCS) materials, which also effectively enhance near-infrared(NIR) reflectance. Moreover, core-etched supernatant solutions are collected and recycled for the synthesis of extracted silica(e-SiO2) process, which successfully applies as filler materials for semiconductor epoxy molding compound(EMC). In detail, B-HST materials, fabricated by the sequential experimental steps of sol-gel, reduction, and sonication-mediated etching method, manifest blackness(L*) of 13.2 similar to black paint and excellent NIR reflectance(31.1%). Consequently, B-HST materials are successfully prepared as LiDAR-reflective black materials. Additionally, core-etched supernatant solution with silanol precursors are employed for synthesis of homogeneous silica filler materials via sol-gel method. As-synthesized silica fillers are incorporated with epoxy resin and carbon black for the preparation of semiconductor EMC. Experimentally synthesized EMC exhibits comparable mechanical-chemical properties to commercial EMC. Conclusively, this study successfully proposes designing procedure and practical experimental method for simultaneously synthesizing the NIR-reflective black materials for self-driving vehicles and EMC materials for semiconductors, which are materials suitable for the industrial 4.0 era, and presented their applicability in future industries.

Three-dimensional porous graphene materials for environmental applications

  • Rethinasabapathy, Muruganantham;Kang, Sung-Min;Jang, Sung-Chan;Huh, Yun Suk
    • Carbon letters
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    • v.22
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    • pp.1-13
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    • 2017
  • Porous materials play a vital role in science and technology. The ability to control their pore structures at the atomic, molecular, and nanometer scales enable interactions with atoms, ions and molecules to occur throughout the bulk of the material, for practical applications. Three-dimensional (3D) porous carbon-based materials (e.g., graphene aerogels/hydrogels, sponges and foams) made of graphene or graphene oxide-based networks have attracted considerable attention because they offer low density, high porosity, large surface area, excellent electrical conductivity and stable mechanical properties. Water pollution and associated environmental issues have become a hot topic in recent years. Rapid industrialization has led to a massive increase in the amount of wastewater that industries discharge into the environment. Water pollution is caused by oil spills, heavy metals, dyes, and organic compounds released by industry, as well as via unpredictable accidents. In addition, water pollution is also caused by radionuclides released by nuclear disasters or leakage. This review presents an overview of the state-of-the-art synthesis methodologies of 3D porous graphene materials and highlights their synthesis for environmental applications. The various synthetic methods used to prepare these 3D materials are discussed, particularly template-free self-assembly methods, and template-directed methods. Some key results are summarized, where 3D graphene materials have been used for the adsorption of dyes, heavy metals, and radioactive materials from polluted environments.

Asymmetric Sythesis of Unnatural L-Amino Acids Using Thermophilic Aromatic L-Amino Acid Transaminase

  • Cho, Byung-Kwan;Seo, Joo-Hyun;Kim, Ju-Han;Lee, Chang-Soo;Kim, Byung-Gee
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.11 no.4
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    • pp.299-305
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    • 2006
  • Aromatic L-amino acid transaminase is an enzyme that is able to transfer the amino group from L-glutamate to unnatural aromatic ${\alpha}-keto$ acids to generate ${\alpha}-ketoglutarate$ and unnatural aromatic L-amino acids, respectively. Enrichment culture was used to isolate thermophilic Bacillus sp. T30 expressing this enzyme for use in the synthesis of unnatural L-amino acids. The asymmetric syntheses of L-homophenylalanine and L-phenylglycine resulted in conversion yields of >95% and >93% from 150 mM 2-oxo-4-phenylbutyrate and phenylglyoxylate, respectively, using L-glutamate as an amino donor at $60^{\circ}C$. Synthesized L-homophenylalanine and L-phenylglycine were optically pure (>99% enantiomeric excess) and continuously pre-cipitated in the reaction solution due to their low solubility at the given reaction pH. While the solubility of the ${\alpha}-keto$ acid substrates is dependent on temperature, the solubility of the unnatural L-amino acid products is dependent on the reaction pH. As the solubility difference between substrate and product at the given reaction pH is therefore larger at higher temperature, the thermophilic transaminase was successfully used to shift the reaction equilibrium toward rapid product formation.

Comparison of the Growth Inhibition by Alpha-Difluoromethylornithin and Hydroxytamoxifen in MCF-7 Human Breast Cancer Cells

  • Kim, Byeong-Gee;Seok, Sorah;Lee, Kyeong-Hee;Lee, Ji-Young;Park, Won-Hyuck
    • Journal of Life Science
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    • v.11 no.1
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    • pp.22-26
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    • 2001
  • In estrogen-dependent MCF-7 human breast cancer cells, $E_2$ at 10 nM stimulated cell proliferation to over 200% compared to the untreated control. EGF and TGF${\alpha}$, which are known as the autocrine/paracrine growth factors induced by $E_2$, also directly stimulated the cell growth in almost as the same extent as $E_2$. DFMO which is the specific inhibitor of ODC could inhibit cell growth even at as low as 0.5 mM. In the treatment with 1 mM DFMO for 4 days, the cell growth was inhibited to 38% of the control. HO-TAM at 1 ${\mu}$M could inhibit the proliferation of MCF-7 cells to 19% of the control. Those inhibitory effects were also found in the cells stimulated with $E_2$, EGF, and TGF${\alpha}$. The inhibitory effects were found even in 2 days of treatment. However, $E_2$, EGF, and TGF${\alpha}$ did not give any effect in the protein synthesis. Neither DFMO or HO-TAM gave any effect on the total protein synthesis. But the pattern of protein secretion was noticeably influenced by the growth stimulants or inhibitors. Proteins of 160, 52, 42, 36, and 32 kDa belonged to the major secretory proteins. Especially, 42 and 36 kDa proteins were most significantly influenced by the treatment of $E_2$, EGF, or TGF$\alpha$. DFMO and HO-TAM inhibited the secretion of these major proteins.

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INDUCTION OF CYTOCHROME P-450 ASSOCIATED MONOOXYGENASE ACTIVITIES BY PHENOBARBITAL AND 3-METHYLCHOLANTHRENE IN PRIMARY CULTURES OF ADULT RAT HEPATOCYTES

  • Park, Seong-Kyu;Ha, Jong-Ryul;Kim, H.M.;Yang, K.H.
    • Toxicological Research
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    • v.3 no.1
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    • pp.1-8
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    • 1987
  • In vitro induction of cytochrome 450 associated monooxygenase activities by phenobarbital (PB) and 3-methylcholanthrene (MC) was investigated in primary cultures of adult rat hepatocytes. PB and MC were added to the culture 24 hr after the initial plating of hepatocytes. A signiftcant increase of the activities of 7-ethoxycoumarin 0-deethylase and aryl hydrocarbon hydroxylase were observed in MC and PB treated culture. MC caused about 500% induction of the initial oxidation rates of both enzymes in 48 hr. However the PB maintained both enzyme activities close to the level of freshly isolated hepatocytes. Biphenyl 4-hydroxylase and aminopyrine N-demethylase activities were also induced by MC and PB. But the level of induction was less than that occuring with 7-ethoxycoumarin 0-deethylase and aryl hydrocarbon hydroxylase. When aflatoxin $B_1$ was added to the hepatocyte cultures which have been treated with MC or PB, it caused a significant increase of the unscheduled DNA synthesis at higher dose of aflatoxin $B_1$ as compared to those of untreated control hepatocyte cultures. The results suggest that microsomal enzyme activities can be selectively controlled preferably in hepatocyte cultures by the in vitro induction method. This principle may be useful for studying the metabolism and other toxicological studies.

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Surface Display of Heme- and Diflavin-Containing Cytochrome P450 BM3 in Escherichia coli: A Whole-Cell Biocatalyst for Oxidation

  • Yim, Sung-Kun;Kim, Dong-Hyun;Jung, Heung-Chae;Pan, Jae-Gu;Kang, Hyung-Sik;Ahn, Tae-Ho;Yun, Chul-Ho
    • Journal of Microbiology and Biotechnology
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    • v.20 no.4
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    • pp.712-717
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    • 2010
  • Cytochrome P450 enzymes (P450s) are involved in the synthesis of a wide variety of valuable products and in the degradation of numerous toxic compounds. The P450 BM3 (CYP102A1) from Bacillus megaterium was the first P450 discovered to be fused to its redox partner, a mammalian-like diflavin reductase. Here, we report the development of a whole-cell biocatalyst using ice-nucleation protein (Inp) from Pseudomonas syringae to display a hemeand diflavin-containing oxidoreductase, P450 BM3 (a single, 119-kDa polypeptide with domains of both an oxygenase and a reductase) on the surface of Escherichia coli. The surface localization and functionality of the fusion protein containing P450 BM3 were verified by flow cytometry and measurement of enzymatic activities. The results of this study comprise the first report of microbial cell-surface display of a heme- and diflavin-containing enzyme. This system should allow us to select and develop oxidoreductases containing heme and/or flavins into practically useful whole-cell biocatalysts for extensive biotechnological applications, including selective synthesis of new chemicals and pharmaceuticals, bioconversion, bioremediation, live vaccine development, and biochip development.

Practical Synthesis of 1,1-Difluoro- or 1-Fluoroalkenes from 2,2,2-Trifluoroacetophenone Derivatives

  • Kang, Min-Hyuk;Lee, Sun-Ah;Kang, Na-Na;Moon, Bong-Jin
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.3022-3030
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    • 2011
  • Since the discovery of the fact that compounds bearing a vinylic fluoride moiety often exhibit remarkable biological activities such as enzyme inhibitors, many synthetic methods for fluorine-substituted vinylic compounds have been developed. The synthesis of selectively fluorinated building blocks, such as arylsubstituted fluoro-alkenes, also has become an area of interest in recent years. Herein we describe a novel and practical method for the synthesis of 1,1-difluoro- and 1-fluoroalkenes starting from easily accessible trifluoroacetophenone derivatives. Various 1,1-difluoro- and 1-fluoroalkenes were prepared by the reaction of the corresponding tosyl hydrazones that were derived from trifluoroacetophenone derivatives by treating with alkyl or aryllithium reagents via addition-elimination and single electron transfer (SET) mechanism.