• Title/Summary/Keyword: ${\alpha}$, ${\omega}$-dicarboxylic acids

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Molecular Dynamic Simulations of the Fatty Acid Bilayer Containing Very Long Chain Transmembrane Dicarboxylic Acids

  • Choi, Yong-Hoon;Yang, Chul-Hak;Kim, Hyun-Won;Jung, Seun-Ho
    • BMB Reports
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    • v.33 no.1
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    • pp.54-58
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    • 2000
  • Recent research results regarding the very long chain transmembrane ${\alpha},{\omega}-dicarboxylic$ components in the membrane of extremophilic eubacteria, such as Sarcina ventriculi, Thennotoga maritima, and Thermoanaerobacter ethanolicus have raised interesting questions concerning the physical and biochemical function on these components in the membrane. In order to understand the dynamic characteristics of these acids which reside in the bilayer membrane, 580 ps molecular dynamic simulations at 300 K were performed for two model systems. These systems were the bilayer with regular chain (C16:0 or C18:1) fatty acid methyl esters and the fatty acid bilayer containing very long chain transmembrane dicarboxylic acid methyl esters (${\alpha},{\omega}-15,16-dimethyltriacotane-dioate$ dimethyl ester; C32:0). Our analyses indicate that very long chain transmembrane dicarboxylic acids have a noticeable influence on the bilayer dynamics at a sub-nanosecond time scale. The center-ofmass mean-squared-displacement (MSD) of regular chain fatty acids adjacent to the very long chain transmembrane dicarboxylic acids decreased, the long-axis order parameter increased, and the reorientational motions of methylene groups were slowed along the hydrocarbon chains. These results indicate that the very long chain transmembrane dicarboxylic acids reduce the molecular order of the whole bilayer membrane.

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Synthesis of Monomers for Polyamide-type TPEs from Oleic Acid (천연 올레인산 기반 폴리아미드계 TPEs 단량체 합성)

  • Koh, Moo-Hyun;Kim, Hyun Su;Kim, Hyeonjeong;Shin, Nara;Yoo, Dongwon;Kim, Young Gyu
    • Elastomers and Composites
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    • v.48 no.1
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    • pp.24-29
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    • 2013
  • We have developed the synthetic processes for the monomers of polyamide-type TPEs (thermoplastic elastomers, TPAEs) obtained from vegetable oil. TPAEs have several superior physical properties to those of thermoplastic elastomers (TPEs). From the common starting material, oleic acid, which is commonly found in various vegetable oils, we have synthesized three ${\omega}$-amino acid monomers ($C_9$, $C_{10}$ and $C_{11}$ ${\omega}$-amino acid) and three ${\alpha}$, ${\omega}$-dicarboxylic acids($C_9$, $C_{10}$ and $C_{11}$ ${\alpha}$, ${\omega}$-dicarboxylic acid) for TPAEs in good yields.

Divergent Process for C10, C11 and C12 ω-Amino Acid and α,ω-Dicarboxylic Acid Monomers of Polyamides from Castor Oil as a Renewable Resource

  • Koh, Moo-Hyun;Kim, Hyeon-Jeong;Shin, Na-Ra;Kim, Hyun-Su;Yoo, Dong-Won;Kim, Young-Gyu
    • Bulletin of the Korean Chemical Society
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    • v.33 no.6
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    • pp.1873-1878
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    • 2012
  • Polyamides have great potentials for diverse applications and the present production of their monomers mostly relies on resources from fossil fuel. Starting from undecylenic acid, a natural resource, we have developed both divergent and efficient processes for $C_{10}$, $C_{11}$ and $C_{12}$ ${\omega}$-amino acid and ${\alpha},{\omega}$-dicarboxylic acid monomers of the polyamides.

Polyesters Biosynthesis of Alcaligenes eutrophus H16(ATCC 17699) from Various Mono- and Dicarboxylic Acids and Diols

  • Song, Jae-Jun;Shin, Yong-Chul
    • Journal of Microbiology and Biotechnology
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    • v.3 no.2
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    • pp.123-128
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    • 1993
  • The polyesters (polyhydroxyalkanoates; PHAs) production capability in a two-step cultivation of Alcaligenes eutrophus H16(ATCC 17699) was investigated by using various organic carbon sources. The carbon sources used included linear $C_2~C_10$ monocarboxylic acids, $C_3~C_10$ dicarboxylic acids, crotonic acid, and several linear vicinal and $\omega$-diols. The polyesters synthesized were characterized by 500 MHz $^1 H-NMR$ spectroscopy, intrinsic viscosity$[\eta]$ measurement in chloroform and differential scanning calorimetry (DSC). The PHAs synthesis data showed that the use of C-odd ($C_3, C_5, and C_7$) monocarboxylic acids resulted in poly(3-hydroxybutyrate-co-3-hydroxyvalerate)(P(3HB-co-3HV) (3HV content ranging 40 to 70 mol%) while the use of $C_9$ substrate gave the copolyester containing only 4 mol% of 3HV. All culture products obtained on $C_3$~C$_{10}$ dicarboxylic acids gave exclusively P(3HB). 500 MHz $^1 H-NMR$ analysis showed that all polyesters synthesized generally contained 1~2 mol% 3HV even for the unrelated substrates such as the carboxylic acids with even number of carbon. When $\alpha, \omega$-diols with even number of carbon were used as substrates, 4-hydroxybutyrate(4HB) was inserted into the polyester chain composed of P(3HB-co-4HB). Vicinal diols were generally not utilized by the bacterium for polyester production.n.

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