• Title/Summary/Keyword: Biological Synthesis

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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.

Development of Fe/$Al_2O_3$ Composite Granules and Activation Conditions for Fischer-Tropsch Synthesis (구형 철-알루미나 입자 제조 및 피셔-트롭시 반응을 위안 전처리 조건 확립)

  • Yoo, Kye-Sang;Lee, Dong-Joon;Jung, Kwang-Deog
    • Transactions of the Korean hydrogen and new energy society
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    • v.19 no.6
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    • pp.545-551
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    • 2008
  • Fe/$Al_2O_3$ composite granules were prepared by combining sol-gel/oil drop method. The shape of granules were mainly determined by composition and concentration of aluminum precursor. The composite granule with the lowest aluminum concentration was synthesized with 0.75M boehmite solution. The prepared granules were tested as a catalyst in the plug-flow reactor for Fischer-Tropsch synthesis. Before the reaction, catalysts were activated by hydrogen reduction and synthesis gas treatment. The activation conditions and aluminum concentration have affected catalytic performance significantly.

Facile Synthesis of Natural Moracin Compounds using Pd(OAc)2/P(tBu)3-HBF4 as a Sonogashira Coupling Reagent

  • Lee, Jae Jun;Yun, So-Ra;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3453-3458
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    • 2014
  • An efficient and practical synthesis of natural moracins, which have diverse range of biological properties including anticancer, antioxidant, and antibacterial activities, has been achieved using $Pd(OAc)_2/P(^tBu)_3-HBF_4$ as a Sonogashira coupling reagent which solved the unreactive problems in case of higher electron density of haloaryl compounds in the reaction. Lowering electron density of halophenol with acetylation and changing Sonogashira coupling reagent from $PdCl_2(PPh_3)_2$ to $Pd(OAc)_2/P(^tBu)_3-HBF_4$ smoothly produce the benzofuran structures in the syntheses of moracins M, N and S. The electron deficient halobenzaldehyde, however, easily forms the benzofuran using original Sonogashira conditions, and utilized for the first synthesis of moracin Y.

The Solid-Phase Synthesis of Amino Acid-Derived Diacetylene Lipids

  • Kim Jong-Man;Park Bum Jun;Chang Eun-Ju;Yi Sung Chul;Suh Dong Hack;Ahn Dong June
    • Macromolecular Research
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    • v.13 no.3
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    • pp.253-256
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    • 2005
  • We prepared amino acid-derived diacetylene monomers using solid-phase organic synthesis. The solid-phase synthetic method allowed for the rapid and efficient preparation of functional diacetylenes. Amino acids having hydrophobic sidechains such as alanine, leucine, and phenylalanine, as well as hydrophilic sidechains such as aspartic acid and lysine, were successfully coupled to the diacetylene lipid. The diacetylene monomers prepared in this way were subjected to routine procedures for the generation of polydiacetylene vesicles. Depending on the nature of the side-chains, pink to blue colored polydiacetylenes were generated.

Total Synthesis of Hepatoprotective Isowogonin and a Synthetic Approach to Wogonin (간보호 효과를 나타내는 Isowogonin의 전합성 및 Wogonin 합성을 위한 반응조건 탐색)

  • Kim, Kwang-Sik;Kim, Hak-Sung
    • YAKHAK HOEJI
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    • v.53 no.6
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    • pp.377-381
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    • 2009
  • Isowogonin, 5,8-dihydroxy-7-methoxyflavone, is a flavonoid isolated from the root of Scutellaria baicalensis Georgi, a medicinal plant traditionally used since the ancient time. It was thought to possess a variety of biological activities, such as antioxidation, anti-inflammation and hepatoprotective effect. But a quantity of isowogonin obtained from Scutellaria baicalensis Georgi is not that enough for in vivo test. There have been no appropriate approaches available for a facile synthesis of isowogonin. So we describe a concise and efficient scheme for synthesis of isowogonin from a commercial available 2,4,6-trimethoxyphenol, which includes the Fries rearrangement and selective demethylation as key steps.

Effect of added mesophase pitch during the pitch synthesis reaction of PFO

  • Kim, Ji Hong;Kim, Jong Gu;Lee, Chul Wee;Lee, Ki Bong;Im, Ji Sun
    • Carbon letters
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    • v.23
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    • pp.48-54
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    • 2017
  • This research considers the effect of added mesophase pitch (MP) as an additive during the pitch synthesis reaction of pyrolyzed fuel oil (PFO). Two effects are generated by adding MP. One is an enhancement of thermal stability due to the high thermal property of the additive; the other is that the volatile compounds that were removed by vaporization of PFO during the thermal reaction can participate in the pitch synthesis reaction ($PFO{\rightarrow}pitch$) more efficiently. The effect differs according to the amount of the additive. When the amount of the additive is less than 7 wt%, the first effect is dominant, whereas the second effect is dominant when the additive amount exceeds 10 wt%.

First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

  • Kim, Si-Jun;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.34 no.1
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    • pp.54-58
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    • 2013
  • Licochalcones, derived from the dried roots of Glycyrrhiza inflata, have been reported to show various biological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging, antibacterial, and PTP1B activity. Licochalcone D has an allyl group on ring A instead of ring B, however, most other natural licochalcones possess the group on ring B. Total synthesis of licochalcone D has not been reported even possessing the strongest anti-inflammatory activity. Therefore, the first total synthesis of licochalcone D has been developed by using water-accelerated [3,3]-sigmatropic rearrangement method.

One-pot Synthesis of Multifunctional Mn3O4/mesoporous Silica Core/shell Nanoparticles for Biomedical Applications

  • Lee, Dong Jun;Lee, Nohyun;Lee, Ji Eun
    • Applied Chemistry for Engineering
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    • v.33 no.1
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    • pp.113-118
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    • 2022
  • Multifunctional nanomaterials based on mesoporous silica nanoparticles (MSN) and metal oxide nanocrystals are among the most promising materials for theragnosis because of their ease of modification and high biocompatibility. However, the preparation of multifunctional nanoparticles requires time-consuming multistep processes. Herein, we report a simple one-pot synthesis of multifunctional Mn3O4/mesoporous silica core/shell nanoparticles (Mn3O4@mSiO2) involving the temporal separation of core formation and shell growth. This simple procedure greatly reduces the time and effort required to prepare multifunctional nanoparticles. Despite the simplicity of the process, the properties of nanoparticles are not markedly different from those of core/shell nanoparticles synthesized by a previously reported multistep process. The Mn3O4@mSiO2 nanoparticles are biocompatible and have potential for use in optical imaging and magnetic resonance imaging.

Synthesis of 2,5-Disubstituted Pyrrolidines from N-Alkenyl and Alkynyl N-Benzoyloxysulfonamides Catalyzed by (CuOTf)2・C6H6

  • Liu, Wei-Min;Liu, Zhen-Hong;Cheong, Wei-Wen;Priscilla, Lu-Yi Teo;Li, Yongxin;Narasaka, Koichi
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.563-569
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    • 2010
  • A new synthetic method of 2,5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyloxysulfonamides by $(CuOTf)_2{\cdot}C_6H_6$ in refluxing dichloroethane. Various N-4- and N-5-alkenyl and alkynyl N-benzoyloxysulfonamides are cyclized to give pyrrolidines. The cyclization proceeds via addition of sulfonamidoyl radicals to intramolecular unsaturated bonds or allylic hydrogen abstraction with the radical intermediates.