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Production of novel platform chemicals from lignin by microbial function

Research Project

Project/Area Number 24380180
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Boundary agriculture
Research InstitutionForestry and Forest Products Research Institute

Principal Investigator

NAKAMURA Masaya  独立行政法人森林総合研究所, きのこ・微生物研究領域, 室長 (50353793)

Co-Investigator(Kenkyū-buntansha) SHIKINAKA Kazuhiro  東京農工大学, 工学系研究科, 助教 (00507189)
KATAYAMA Yoshihiro  日本大学, 生物資源科学部, 教授 (10214339)
OTSUKA Yuichiro  森林総合研究所, バイオマス化学研究領域, 主任研究員 (80455261)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥16,770,000 (Direct Cost: ¥12,900,000、Indirect Cost: ¥3,870,000)
Fiscal Year 2014: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2013: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2012: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywordsリグニン / プロトカテク酸3,4-ジオキシゲナーゼ / 2-ピロン-4,6-ジカルボン酸 / 3-カルボキシムコノラクトン / バニリン / プロトカテク酸4,5-ジオキシゲナーゼ / 2-ピロン4,6-ジカルボン酸 / アミド化合物 / ポリエステル / カルボキシムコノラクトン / 3-カルボキシムコノラクトンジクロリド化合物 / バニリン酸 / バイオマス
Outline of Final Research Achievements

We have produce 2-pyrone-4,6-dicarboxylic acid (PDC) and 3-carboxymuconolactone (3CML) as a platform chemicals with genes coding for vanillin dehydrogenase (lig V), vanillic acid demethylase (van AB), protocatechuic acid 4,5-dioxygenase (lig AB) and 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase (lig C) from the lignin degrading soil bacterium, Sphingobium sp. SYK-6, and protocatechuic acid 3,4-dioxygenasd (pca HG) from aromatic compound degrader P.putida KT2440, 3-carboxy-cis,cis-muconate lactonizing enzyme gene (pca B) from Neurpspora crassa respectively.
The PDC polyesters bearing the aromatic groups adjacent to the PDC nuclei exhibited high Td5 (5 wt% loss temperature), good enough to utilize them as thermoplastics. The 3-CML was converted into the corresponding acid chloride derivative, 3-CML dichloride and amid derivative with n-hexyl isocyanate respectively for polymerization.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (14 results)

All 2014 2013 2012

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 1 results) Presentation (6 results) Book (1 results)

  • [Journal Article] リグニンの微生物代謝中間体2ピロン4,6-ジカルボン酸(PDC)の生産と利用技術開発2014

    • Author(s)
      中村雅哉、大塚祐一郎、敷中一洋、重原淳孝、片山義博
    • Journal Title

      木材工業技術短信

      Volume: 32 Pages: 1-11

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Polysubstituted Benzenes from 2-Pyrone-4,6-dicarboxylic Acid2014

    • Author(s)
      OKURA Keisho, TAMURA Ryuichi, SHIGEHARA Kiyotaka, MASAI Eiji, NAKAMURA Masaya, OTSUKA Yuichiro, KATAYAMA Yoshihiro, NAKAO Yoshiaki
    • Journal Title

      Chemistry Letters

      Volume: 43 Pages: 1349-1351

    • NAID

      130004427141

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] アシル化リグニンおよびリグニンの熱可塑性コンポジット2013

    • Author(s)
      敷中一洋, 江頭俊, 大塚祐一郎, 中村雅哉, 大原誠資, 重原淳孝
    • Journal Title

      繊維学会誌

      Volume: 69 Pages: 90-95

    • NAID

      10031166905

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 植物バイオマス「リグニン」由来低分子”PDC”を用いたバイオベース材料2013

    • Author(s)
      敷中一洋、重原淳孝
    • Journal Title

      接着の技術

      Volume: 33 Pages: 11-16

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thermoplastic Polyesters of 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin2013

    • Author(s)
      Kazuhiro Shikinaka, Yoshiki Hashimoto, Shinya Kajita, Eiji Masai, Yoshihiro Katayama, Masaya Nakamura, Yuichiro Otsuka, Seiji Ohara, Kiyotaka Shigehara
    • Journal Title

      繊維学会誌

      Volume: 69巻 Pages: 39-47

    • NAID

      10031141512

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] リグニン由来エポキシ樹脂の硬化挙動2012

    • Author(s)
      長谷川雄紀,敷中一洋,梶田真也,政井英司,片山義博,大塚祐一郎,中村雅哉,大原誠資,重原淳孝
    • Journal Title

      繊維学会誌

      Volume: 68巻 Pages: 73-78

    • NAID

      10030519626

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] リグニンからバイオプロセスにより誘導されるグリーンケミカルス 2ピロン4,6-ジカルボン酸(PDC) の生産と利用技術開発2012

    • Author(s)
      中村雅哉,大塚祐一郎,政井英司,敷中一洋,重原淳孝,片山義博
    • Journal Title

      AROMA RESEARCH

      Volume: 13巻 Pages: 323-327

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] 木質バイオマスリグニン由来分子「PDC」によるセシウムの選択的捕集2014

    • Author(s)
      敷中一洋、大塚祐一郎、井口友莉、中村雅哉、政井英司、片山義博、重原淳孝
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール(札幌市)
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] Production of Novel Platform Chemicals from Aromatic Wood Biomass by Microbial Fermentation.2014

    • Author(s)
      Masaya Nakamura, Yasumasa Miyazaki, Yuichiro Otsuka, Kazuhiro Shikinaka, Yoshihiro Katayama
    • Organizer
      Australian Society for Microbiology Annual Scientific Meeting
    • Place of Presentation
      Pullman Melbourne Albert Park (Australia)
    • Year and Date
      2014-07-06 – 2014-07-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] FUNCTIONAL METABOLIC INTERMEDIATE (2-PYRON-4,6-DICARBOXYLIC ACID) FROM LIGNIN2013

    • Author(s)
      中村雅哉、大塚祐一郎、敷中一洋、重原淳孝、片山義博
    • Organizer
      14th International Waste Management and Landfill Symposium
    • Place of Presentation
      Forte Village, Sardinia, Italiy
    • Related Report
      2013 Annual Research Report
  • [Presentation] リグニン生分解中間物PDCが形成する自己組織化材料2013

    • Author(s)
      敷中一洋、金田恵介、片山義博、政井英司、中村雅哉、大塚祐一郎、大原誠資、重原淳孝
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学角間キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] 2-PYR0N-4, 6-DICARBOXYLIC ACID AS A SOURCE OF GREEN-PLASTICS FROM LIGNI N-DERIVED STABLE METABOLIC INTERMEDIATE2012

    • Author(s)
      Masaya Nakamura, Yuichiro Otsuka, Eiji Masai, Kazuhiro Shikinaka, Kiyotaka Shigehara, Yoshihiro Katayama
    • Organizer
      International Symposium on Energy From Biomass and Waste
    • Place of Presentation
      an Servolo, Venice (Italy)
    • Year and Date
      2012-11-12
    • Related Report
      2012 Annual Research Report
  • [Presentation] リグニン生分解中間物「PDC」由来エンジニアリングプラスチックフィルム2012

    • Author(s)
      敷中一洋、橋本佳樹、政井英司、大塚祐一郎、中村雅哉、大原誠資、片山義博、重原淳孝
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋国際会議場(愛知県名古屋市)
    • Year and Date
      2012-09-19
    • Related Report
      2012 Annual Research Report
  • [Book] リグニン利用の最新動向2013

    • Author(s)
      中村雅哉、大塚祐一郎、政井英司、敷中一洋、重原淳孝、片山義博
    • Total Pages
      10
    • Publisher
      シーエムシー出版
    • Related Report
      2013 Annual Research Report

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Published: 2012-04-24   Modified: 2019-07-29  

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