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2007 Fiscal Year Final Research Report Summary

Preparation of mew functional dehydrogenative polymer (DHP) from γ-substituted monolignol derivatives

Research Project

Project/Area Number 18580162
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 林産科学・木質工学
Research InstitutionKyoto University

Principal Investigator

TAKANO Toshiyuki  Kyoto University, Graduate School of Agriculture, Division of Forest & Biomaterials Science, Associate Professor (50335303)

Co-Investigator(Kenkyū-buntansha) NAKATSUBO Fumiaki  Kyoto University, Graduate School of Agriculture, Division of Forest & Biomaterials Science, Professor (10027170)
KAMITAKAHARA Hiroshi  Kyoto University, Graduate School of Agriculture, Division of Forest & Biomaterials Science, Assistant Professor (10293911)
Project Period (FY) 2006 – 2007
KeywordsLignin / Monolignol / Sinapyl alcohol / Toll-like receptor-ligand / Ferulic acid / Two dimensional polymerization / シナピルアルコール
Research Abstract

Two type of γ-substituted monolignol derivatives were selected ; one was monolignol glycoside in which a hydrophilic group (D-glucose) was introduced, the another was ferulic alkyl ester in which a hydrophobic group (n-decanoyl group) was introduced., and their dehydrogenative polymerizations were investigated.
The dehydrogenative polymerizations of monolignol glycoside proceeds homogeneously to afford water soluble DHP, whereas the polymerization of monolignol proceeds heterogeneously. It was found that the polymerization behaviors in the polymerizations of monolignol glycoside were reflected with those in the polymerizations of monolignol. And the in suit UV analysis of the polymerization of monolignol glycoside revealed that unexpected stability of the intermediate (quinine methide) is one of the reasons for the peculiar polymerization behaviors of sinapyl alcohol.
The dehydrogenative polymerizations of ferulic alkyl ester by two dimensional method and by micelle method were carried out. The DHPs obtained are quietly different from DHP by normal dehydrogenative polymerization, suggesting that the hydrophobic group significantly influenced to the chemical structure of DHP.

  • Research Products

    (18 results)

All 2008 2007 2006

All Journal Article (8 results) (of which Peer Reviewed: 4 results) Presentation (10 results)

  • [Journal Article] "Azide ion as a quinone methide scavenger in the horseradish peroxidase-catalyzed polymerization of sinapyl alcohol."2008

    • Author(s)
      Yuki Tobimatsu, et. al.
    • Journal Title

      Journal of Wood Science 54

      Pages: 87-89

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] "Studies on the dehydrogenative polymerization from monolignol β-glycosides. Part 3. Horseradish peroxidase catalyzed dehydrogenative polymerization of triandrin and isosyringin."2008

    • Author(s)
      Yuki Tobimatsu, et. al.
    • Journal Title

      Journal of Wood Chemistry and Technology (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Azide ion as a quinone methide scavenger in the horseradish peroxidase-catalyzed polymerization of sinapyl alcohol.2008

    • Author(s)
      Yuki, Tobimatsu, Toshiyuki, Takano, Hiroshi, Kamitakahara, Fumiaki, Nakatsubo
    • Journal Title

      Journal of Wood Science 54

      Pages: 87-89

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] "Studies on the dehydrogenative polymer (DHP) from monolignol β-glycosides. Part 3. Horseradish peroxidase catalyzed dehydrogenative polymerization of triandrin and isosyringin."2008

    • Author(s)
      Yuki, Tobimatsu, Toshiyuki, Takano, Hiroshi, Kamitakahara, Fumiaki, Nakatsubo
    • Journal Title

      Journal of Wood Chemistry and Technology (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] "Studies on the dehydrogenative polymerization from monolignol β-glycosides. Part 1. Synthesis of monolignol β-glycosides, (E)-isoconiferin, (E)-isosyringin, (E)-triandrin."2006

    • Author(s)
      Toshiyuki Takano, et. al.
    • Journal Title

      Journal of Wood Chemistry and Technology 26

      Pages: 215-229

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] "Studies on the dehydrogenative polymerization from monolignol β-glycosides. Part 2. Horseradish peroxidase catalyzed dehydrogenative polymerization of isoconiferin."2006

    • Author(s)
      Yuki Tobimatsu, et. al.
    • Journal Title

      Holzforschung 60

      Pages: 513-518

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] "Studies on the dehydrogenative polymer (DHP) from monolignol β-glycosides. Part 1. Synthesis of monolignol β-glycosides, (E)-isoconiferin, (E)-isosyringin, (E)-triandrin."2006

    • Author(s)
      Toshiyuki, Takano, Yuki, Tobimatsu, Takashi, Hosoya, Takefumi, Hattori, Jiro, Ohnishi, Mariko, Takano, Hiroshi Kamitakahara, Fumiaki, Nakatsubo
    • Journal Title

      Journal of Wood Chemistry and Technology 26

      Pages: 215-229

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] "Studies on the dehydrogenative polymer (DHP) from monolignol β-glycosides. Part 2. Horseradish peroxidase catalyzed dehydrogenative polymerization of isoconiferin."2006

    • Author(s)
      Yuki, Tobimatsu, Toshiyuki, Takano, Hiroshi, Kamitakahara, Fumiaki, Nakatsubo
    • Journal Title

      Holzforschung 60

      Pages: 513-518

    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] "求核試薬存在下におけるシナピルアルコールの脱水素重合"2008

    • Author(s)
      飛松 裕基
    • Organizer
      第58回日本木材学会大会
    • Place of Presentation
      つくば国際会議場(エポカルつくば)
    • Year and Date
      2008-03-18
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Dehydrogenative polymerization of sinapyl alcohol in the presence of nucleophile2008

    • Author(s)
      Yuki, Tobimatsu, Hiroshi, Kamitakahara, Toshiyuki, Takano, Fumiaki, Nakatsubo
    • Organizer
      58th Annual Meeting of the Japan Wood Research Society
    • Place of Presentation
      Tsukuba International Congress Center
    • Year and Date
      2008-03-18
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] "モノリグノール配糖体によるシリンギル型DHPの生成挙動の解析"2007

    • Author(s)
      飛松 裕基
    • Organizer
      第52回リグニン討論会
    • Place of Presentation
      宇都宮大学大学会館
    • Year and Date
      2007-11-14
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Analysis of dehygrogenative polymerization behaviors of syringyl type monoliginol β-glycosides.2007

    • Author(s)
      Yuki, Tobimatsu, Hiroshi, Kamitakahara, Toshiyuki, Takano, Fumiaki, Nakatsubo
    • Organizer
      52th Ligninsymposium
    • Place of Presentation
      Utsunomiya University University Hall
    • Year and Date
      2007-11-14
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] "モノリグノール配糖体のHRP触媒脱水素重合Part 2."2006

    • Author(s)
      飛松 裕基
    • Organizer
      第51回リグニン討論会
    • Place of Presentation
      北海道大学学術交流会館
    • Year and Date
      2006-10-27
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] フェルラ酸ステアリルの酵素触媒二次元重合2006

    • Author(s)
      坂本昌平
    • Organizer
      第51回リグニン討論会
    • Place of Presentation
      北海道大学学術交流会館
    • Year and Date
      2006-10-27
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Dehydrogenative polymerizations of monolignol β-glycosides. Part 2.2006

    • Author(s)
      Yuki, Tobiraatsu, Hiroshi, Kamitakahara, Toshiyuki, Takano, Fumiaki, Nakatsubo
    • Organizer
      51th Lignin symposium
    • Place of Presentation
      Hokkaido University Conference Hall
    • Year and Date
      2006-10-26
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Two dimensional polymerizations of ferulic stearate2006

    • Author(s)
      Shohei, Sakamoto, Hiroshi, Kamitakahara, Toshiyuki, Takano, Fumiaki, Nakatsubo
    • Organizer
      51th Lignin symposium
    • Place of Presentation
      Hokkaido University Conference Hall
    • Year and Date
      2006-10-26
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] "Dehydrogenative polymerizations of monolignol β-glycosides"2006

    • Author(s)
      Toshiyuki Takano
    • Organizer
      9th European Workshop on Lignocellulosics and Pulp
    • Place of Presentation
      オーストリア農科大学(BOKU)
    • Year and Date
      2006-08-29
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Dehydrogenative polymerizations of monolignol β-glycosides2006

    • Author(s)
      Toshiyuki, Takano, Yuki, Tobimatsu, Hiroshi, Kamitakahara, Fumiaki, Nakatsubo
    • Organizer
      9th European Workshop on Lignocallulosics and Pulp
    • Place of Presentation
      University of Natural Resources and Applied Life Sciences, Vienna
    • Year and Date
      2006-08-29
    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2010-02-04  

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