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Biosynthesis of chiral polymer with stereochmical reversion

Research Project

Project/Area Number 19K22069
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 26:Materials engineering and related fields
Research InstitutionKobe University (2022)
Tokyo University of Agriculture (2019-2021)

Principal Investigator

Taguchi Seiichi  神戸大学, 科学技術イノベーション研究科, 特命教授 (70216828)

Project Period (FY) 2019-06-28 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2021: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2020: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2019: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsバイオポリマー / バイオプラスチック / 立体化学特異性 / 鏡像異性体 / CoA転移酵素 / 重合酵素 / PHA / 3HB / 立体化学 / キラリティー / 基質特異性 / 微生物重合 / ポリマー / キラリティ ー / ポリマー材料
Outline of Research at the Start

化学重合研究において、光学活性モノマーの立体化学を精密制御できる触媒を開発し光学純度の高いポリマーを合成することは、基礎・応用の両面において重要な課題である。一方、微生物産生ポリマーであるP(3HB)は、(R)体モノマーからなる超高光学純度ポリマーであり、細胞システム(関連酵素群の厳密な立体認識選択性)の特質が生かされている。「本来(R)体モノマーにしか反応選択性を示さない重合酵素を、(S)体モノマーを認識しポリマー鎖内に取り込めるように人工的に改変できないか?」というのが、本研究の中心課題である。この研究を通じて得られることは、重合酵素の基質認識を立体化学の視点から明らかにできることにある。

Outline of Final Research Achievements

Biodegradable polyester, P(3HB), consists of 3-hydroxybutyrate (3HB) monomer with a (R) stereochemical conformation can be synthesized by P(3HB) polymerase. I attempted to generate (S)-3HB-CoA via modification of propionyl-CoA transferase (PCT) with a loosen stereochemical reaction. As for final polymerization step, a weak reactivity of evolved PHA synthase with a main chain-based 2-hydroxy reactivity towards (S)-3HB-CoA was detected through fluorescent microscopic observation.

Academic Significance and Societal Importance of the Research Achievements

高分子材料における光学純度は、物性を規定する重要な要因である。生分解性プラスチック素材であるバイオポリマーPHAも同様である。PHAの微生物重合系では、関わる酵素の立体化学認識により、(R)体モノマーから成る高光学純度ポリマーが合成される。本研究では、立体化学反転した(S)体モノマー3HBから成るポリマーの微生物合成に挑戦した。本取り組みは、国内外を問わず全く新規のチャレンジであり、独創性に富んでいる。本研究により、モノマー及びポリマーの合成において、この難度の高いハードルを突破できる基礎的な可能性を得ることができた。本知見は、微生物重合に新しい視点とポリマー材料を提供できる点で意義がある。

Report

(5 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (45 results)

All 2023 2022 2021 2020 2019

All Journal Article (21 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 21 results,  Open Access: 16 results) Presentation (11 results) (of which Int'l Joint Research: 6 results,  Invited: 11 results) Book (10 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Exploring Class I polyhydroxyalkanoate synthases with broad substrate specificity for polymerization of structurally diverse monomer units2023

    • Author(s)
      Sivashankari Ramamoorthi M、Mierzati Maierwufu、Miyahara Yuki、Mizuno Shoji、Nomura Christopher T.、Taguchi Seiichi、Abe Hideki、Tsuge Takeharu
    • Journal Title

      Frontiers in Bioengineering and Biotechnology

      Volume: 11 Pages: 1114946-1114946

    • DOI

      10.3389/fbioe.2023.1114946

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] メンブレンベシクル創発の新原理ーバイオプラスチック合成が“引き金”2023

    • Author(s)
      田口精一、高相昊
    • Journal Title

      日本農芸化会会誌

      Volume: 61 Pages: 217-219

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enhanced production of (R)-3-hydroxybutyrate oligomers by coexpression of Molecular Chaperones in Recombinant Escherichia coli Harboring a polyhydroxyalkanoate synthase derived from Bacillus cereus YB-42022

    • Author(s)
      Saki Goto, Yuki Miyahara, Seiichi Taguchi, Takeharu Tsuge, Ayaka Hiroe
    • Journal Title

      Microorganisms

      Volume: 10 Issue: 2 Pages: 458-470

    • DOI

      10.3390/microorganisms10020458

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Poly(3-mercapto-2-methylpropionate), a Novel α-Methylated Bio-Polythioester with Rubber-like Elasticity, and Its Copolymer with 3-hydroxybutyrate: Biosynthesis and Characterization2022

    • Author(s)
      Ceneviva Lucas Vinicius Santini、Mierzati Maierwufu、Miyahara Yuki、Nomura Christopher T.、Taguchi Seiichi、Abe Hideki、Tsuge Takeharu
    • Journal Title

      Bioengineering

      Volume: 9 Issue: 5 Pages: 228-228

    • DOI

      10.3390/bioengineering9050228

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Optimization of Culture Conditions for Secretory Production of 3-Hydroxybutyrate Oligomers using recombinant Escherichia coli2022

    • Author(s)
      Tetsuo Sakurai, Shoji Mizuno, Yuki Miyahara, Ayaka Hiroe, SEIICHI TAGUCHI, Takeharu Tsuge
    • Journal Title

      Frontiers in Bioengineering and Biotechnology: Bioprocess Engineering

      Volume: 10 Pages: 1-9

    • DOI

      10.3389/fbioe.2022.829134

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Controllable secretion of multilayer vesicles driven by microbial polymer accumulation2022

    • Author(s)
      Koh Sangho、Sato Michio、Yamashina Kota、Usukura Yuki、Toyofuku Masanori、Nomura Nobuhiko、Taguchi Seiichi
    • Journal Title

      Scientific Reports

      Volume: 12 Issue: 1 Pages: 1-9

    • DOI

      10.1038/s41598-022-07218-z

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] 世界へ発信する生分解性プラスチック~「脱炭素化社会」に向けて~ 特集によせて2022

    • Author(s)
      田口精一
    • Journal Title

      生物工学会誌

      Volume: 100 Pages: 476-477

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 生分解性「多元ポリ乳酸LAHB」の研究ストーリー:乳酸重合酵素誕生・オリゴマー分泌生産発見・膜小胞創発2022

    • Author(s)
      田口精一、高相昊
    • Journal Title

      生物工学会誌

      Volume: 100 Pages: 483-488

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Editorial: Microbial Production of Biopolyesters and Their Building Blocks: Opportunities and Challenges2021

    • Author(s)
      Huibin Zou, Seiichi Taguchi, David Bernard Levin
    • Journal Title

      Front. Bioeng. Biotechnol.

      Volume: 9 Pages: 777265-777265

    • DOI

      10.3389/fbioe.2021.777265

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] The influence of medium composition on the microbial secretory production of hydroxyalkanoate oligomers2021

    • Author(s)
      Mizuno S, Sakurai T, Nabasama M, Kawakami K, Hiroe A, Taguchi S, Tsuge T
    • Journal Title

      The Journal of General and Applied Microbiology

      Volume: 67 Issue: 4 Pages: 134-141

    • DOI

      10.2323/jgam.2020.09.002

    • NAID

      130008106876

    • ISSN
      0022-1260, 1349-8037
    • Related Report
      2021 Research-status Report 2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Microbial oversecretion of (R)-3-hydroxybutyrate oligomer with diethylene glycol terminal as a macromonomer for polyurethane synthesis2021

    • Author(s)
      Hiroe Ayaka、Sakurai Tetsuo、Mizuno Shoji、Miyahara Yuki、Goto Saki、Yamada Mariko、Tsuge Takeharu、Taguchi Seiichi
    • Journal Title

      International Journal of Biological Macromolecules

      Volume: 167 Pages: 1290-1296

    • DOI

      10.1016/j.ijbiomac.2020.11.083

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Microbial Production of Biodegradable Lactate-Based Polymers and Oligomeric Building Blocks From Renewable and Waste Resources2021

    • Author(s)
      Nduko John Masani、Taguchi Seiichi
    • Journal Title

      Frontiers in Bioengineering and Biotechnology

      Volume: 8 Pages: 1-18

    • DOI

      10.3389/fbioe.2020.618077

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Superior thermal stability and fast crystallization behavior of a novel, biodegradable α-methylated bacterial polyester2021

    • Author(s)
      Furutate Sho、Kamoi Junichi、Nomura Christopher T.、Taguchi Seiichi、Abe Hideki、Tsuge Takeharu
    • Journal Title

      NPG Asia Materials

      Volume: 13 Issue: 1 Pages: 11-31

    • DOI

      10.1038/s41427-021-00296-x

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Effect of introducing a disulfide bridge on the thermostability of microbial transglutaminase from Streptomyces mobaraensis2021

    • Author(s)
      Yokoyama Keiichi、Ogaya Daisuke、Utsumi Hiroe、Suzuki Mototaka、Kashiwagi Tatsuki、Suzuki Eiichiro、Taguchi Seiichi
    • Journal Title

      Applied Microbiology and Biotechnology

      Volume: 105 Issue: 7 Pages: 2737-2745

    • DOI

      10.1007/s00253-021-11200-6

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Microbial Polyhydroxyalkanoates (PHAs): From Synthetic Biology to Industrialization2020

    • Author(s)
      Miyahara Yuki、Hiroe Ayaka、Sato Shunsuke、Tsuge Takeharu、Taguchi Seiichi
    • Journal Title

      Biotechnology Journal

      Volume: 14 Pages: 231-264

    • DOI

      10.1002/9783527818310.ch8

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Bioconversion of biphenyl to a polyhydroxyalkanoate copolymer by Alcaligenes denitrificans A412020

    • Author(s)
      Yajima Taito、Nagatomo Mizuki、Wakabayashi Aiko、Sato Michio、Taguchi Seiichi、Maeda Michihisa
    • Journal Title

      AMB Express

      Volume: 10 Issue: 1 Pages: 155-163

    • DOI

      10.1186/s13568-020-01093-5

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Isolation of poly[d-lactate (LA)-co-3-hydroxybutyrate)]-degrading bacteria from soil and characterization of d-LA homo-oligomer degradation by the isolated strains2020

    • Author(s)
      Chiaki Hori, Tomohiro Sugiyama, Kodai Watanabe, Jian Sun,Yuu Kamada Toshihiko Ooi, Takuya Isono,Toshifumi Satoh, Shin-ichiro Sato, Seiichi Taguchi, Ken'ichiro Matsumoto
    • Journal Title

      Polymer Degradation and Stability

      Volume: 179 Pages: 109231-109231

    • DOI

      10.1016/j.polymdegradstab.2020.109231

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Changed bacterial community in the river water samples upon introduction of biodegradable poly(3-hydroxybutyrate)2020

    • Author(s)
      Kadoya R, Tanaka N, Fujita N, Shiwa Y, Taguchi S
    • Journal Title

      Polymer Degradation and Stability

      Volume: 176 Pages: 109144-109144

    • DOI

      10.1016/j.polymdegradstab.2020.109144

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Microbial secretion platform for 3-hydroxubutyrate oligomer and its end-capped forms using chain transfer reaction-mediated polyhydroxyalkanoate synthases2019

    • Author(s)
      Y. Miyahara, A. Hiroe, T. Tsuge, S. Taguchi
    • Journal Title

      Biotechnol. J.

      Volume: 14 Issue: 12 Pages: 321-328

    • DOI

      10.1002/biot.201900201

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ribulose-1,5-bisphosphate carboxylase/oxidase (RuBisCO)-mediated de novo synthesis of glycolate-based polyhydroxyalkanoate in Escherichia coli.2019

    • Author(s)
      Matsumoto K, Saito J, Yokoo T, Hori C, Nagata A, Kudoh Y, Ooi T, Taguchi S.
    • Journal Title

      J. Biosci. Bioeng.

      Volume: 印刷中 Issue: 3 Pages: 302-306

    • DOI

      10.1016/j.jbiosc.2019.03.002

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Microbial Production and Properties of LA-based Polymers and Oligomers from Renewable Feedstock2019

    • Author(s)
      Nduko John Masani、Taguchi Seiichi
    • Journal Title

      Part of the Biofuels and Biorefineries book series (BIOBIO, volume 9)

      Volume: 9 Pages: 361-390

    • DOI

      10.1007/978-981-13-3768-0_12

    • ISBN
      9789811337673, 9789811337680
    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] Microbial factory for lactate-based polymer/oligomer: biosynthesis, properties and biodegradation2022

    • Author(s)
      Seiichi Taguchi
    • Organizer
      The 1st International Symposium on Low-Carbon Development and Green Bio-manufacturing
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Advanced microbial polymer/oligomer factory: biosynthesis and biodegradation2021

    • Author(s)
      Seiichi TAGUCHI
    • Organizer
      AFOB
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 環境循環材料としての多元ポリ乳酸P(LAHB):生合成&生分解2021

    • Author(s)
      田口精一
    • Organizer
      高分子学会
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] 天然ポリマーから創発した多元ポリ乳酸LAHB2020

    • Author(s)
      田口精一
    • Organizer
      (公益社団法人)日本化学会 第10回CSJ化学フェスタ(2020)招待講演
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] バイオプラスチックの生合成と生分解:多元ポリ乳酸研究の進展と関連分野の動向2020

    • Author(s)
      田口精一
    • Organizer
      (公益社団法人)新化学技術推進協会 ライフサイエンス技術部会・反応分科会
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] Bio-oligomer provides insights into secretion and mechanistic biodegradation of lactate-based polymers2019

    • Author(s)
      S. Taguchi
    • Organizer
      The 7th International Conference on Bio-based Polymers
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthetic biology for biocompatible and biodegradable polymers from renewable biomass2019

    • Author(s)
      S. Taguchi
    • Organizer
      The 3rd International Biotechnology Congress (IBC-2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Biocompatible and biodegradable PLA-copolymers biosynthesized by microbial platform from renewable feedstock2019

    • Author(s)
      S. Taguchi
    • Organizer
      10th International Conference on Biopolymers and Bioplastics
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 海洋分解など地球環境に貢献するバイオプラスチック、テーマ:海のゴミと食品ロス削減~命を思いやる想像力を育てる~(海と日本2019)2019

    • Author(s)
      田口精一
    • Organizer
      日本海老協会
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] バイオプラスチックの合成生物学=生合成×高分子化学2019

    • Author(s)
      田口精一
    • Organizer
      (公益社団法人)新化学技術推進協会のライフサイエンス技術部会・反応分科会・技術セミナー、(公益社団法人)新化学技術推進協会)
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 多元ポリ乳酸;基礎物性・機能部材化・生分解性12316;、テーマ<<海洋プラスチック問題解決に向けた>>生分解、バイオマスプラスチックの材料設計、将来展望2019

    • Author(s)
      田口精一
    • Organizer
      (株)技術情報協会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Book] バイオリアクターのスケールアップと物質生産事例2021

    • Author(s)
      田口精一
    • Total Pages
      515
    • Publisher
      NTS出版
    • Related Report
      2021 Research-status Report
  • [Book] バイオリアクターのスケールアップと物質生産事例集 乳酸ポリマーP(LAHB)の微生物生産2021

    • Author(s)
      田口精一
    • Total Pages
      12
    • Publisher
      技術情報協会
    • ISBN
      9784861048302
    • Related Report
      2020 Research-status Report
  • [Book] 生分解性プラスチックの環境配慮設計指針 多元ポリ乳酸の合成/分解の交差点:「オリゴマー」2020

    • Author(s)
      田口精一
    • Total Pages
      11
    • Publisher
      シーエムシー出版
    • ISBN
      9784781314877
    • Related Report
      2020 Research-status Report
  • [Book] 生分解性プラスチックの環境配慮設計指針 非天然ポリヒドロキシアルカン酸の分解性とその評価法2020

    • Author(s)
      松本謙一郎、田口精一
    • Total Pages
      11
    • Publisher
      シーエムシー出版
    • ISBN
      9784781314877
    • Related Report
      2020 Research-status Report
  • [Book] 化学と生物 セミナー室 多元ポリ乳酸」の生合成と生分解:メカニズム解明の鍵"オリゴマー"2020

    • Author(s)
      田口精一
    • Total Pages
      7
    • Publisher
      (公益社団法人)日本農芸化学会
    • Related Report
      2020 Research-status Report
  • [Book] 「食品の包装」 特集:バイオプラスチック バイオプラスチック「多元ポリ乳酸」:生産プロセスから機能部材化・生分解性まで2020

    • Author(s)
      田口精一
    • Total Pages
      12
    • Publisher
      包装食品技術協
    • Related Report
      2020 Research-status Report
  • [Book] Microbial production and properties of LA-based polymers and oligomers from renewable feedstock2019

    • Author(s)
      J. M. Nduko, S. Taguchi
    • Total Pages
      30
    • Publisher
      Springer Nature
    • ISBN
      9789811337680
    • Related Report
      2019 Research-status Report
  • [Book] プラスチックの資源循環に向けたグリーンケミストリーの要素技術2019

    • Author(s)
      田口精一
    • Total Pages
      336
    • Publisher
      シーエムシー出版
    • ISBN
      9784781314440
    • Related Report
      2019 Research-status Report
  • [Book] 生分解性プラスチックの環境配慮設計指針2019

    • Author(s)
      田口精一、松本謙一郎
    • Total Pages
      291
    • Publisher
      シーエムシー出版
    • ISBN
      9784781314877
    • Related Report
      2019 Research-status Report
  • [Book] 生分解性プラスチックの素材・技術開発~海洋プラスチック汚染問題を見据えて~2019

    • Author(s)
      田口精一、山田美和
    • Total Pages
      366
    • Publisher
      エヌ・ティー・エス出版
    • ISBN
      9784860436230
    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] 水環境における微生物の分解性に優れた生分解性樹脂組成物及びその成形体2023

    • Inventor(s)
      田口精一ら
    • Industrial Property Rights Holder
      田口精一ら
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2023-030520
    • Filing Date
      2023
    • Related Report
      2022 Annual Research Report
  • [Patent(Industrial Property Rights)] メンブレンベシクルの生産方法及びメンブレンベシクルを利用した物質生産方法2023

    • Inventor(s)
      田口精一、高相昊
    • Industrial Property Rights Holder
      田口精一、高相昊
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2023-030519
    • Filing Date
      2023
    • Related Report
      2022 Annual Research Report
  • [Patent(Industrial Property Rights)] 転写調節によるポリ乳酸んの合成法2022

    • Inventor(s)
      島田友裕、田口精一
    • Industrial Property Rights Holder
      島田友裕、田口精一
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2022-021439
    • Filing Date
      2022
    • Related Report
      2022 Annual Research Report

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Published: 2019-07-04   Modified: 2024-01-30  

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