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Biosynthesis of the Carbonylmethylene Structure Found in a Class of Pseudotripeptides, Ketomemicins

Research Project

Project/Area Number 15H03110
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Biomolecular chemistry
Research InstitutionHokkaido University

Principal Investigator

Dairi Tohru  北海道大学, 工学研究院, 教授 (70264679)

Co-Investigator(Kenkyū-buntansha) 濱野 吉十  福井県立大学, 生物資源学部, 教授 (50372834)
Co-Investigator(Renkei-kenkyūsha) SATOH YASUHARU  北海道大学, 大学院工学研究院, 助教 (30360928)
OGASAWARA YASUSHI  北海道大学, 大学院工学研究院, 助教 (20732986)
MORITA HIROYUKI  富山大学, 和漢医薬学総合研究所, 教授 (20416663)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000)
Fiscal Year 2017: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2016: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥10,270,000 (Direct Cost: ¥7,900,000、Indirect Cost: ¥2,370,000)
Keywords放線菌 / ATP-grasp ligase / シュードトリペプチド / カルボニルメチレン構造 / 生合成 / ペプチドリガーゼ / シュードペプチド / カルボニルメチレン / ATP-grasp / ケトメミシン
Outline of Final Research Achievements

We recently discovered novel pseudotripeptides, ketomemicins, which possess a C-terminal pseudodipeptide connected with a carbonyl methylene instead of an amide bond. The carbonyl methylene structure is stable than amide bond and its biological significance has been shown in several natural and synthetic compounds. Despite the biological significances of these compounds, little is known about its biosynthetic machinery. We therefore examined it by in vitro studies with recombinant enzymes. Consequently, an aldolase, dehydratase, PLP-dependent glycine-C-acetyltransferase, and dehydrogenase were revealed to be involved in the formation of the pseudodipeptide with malonyl-CoA and phenylpyruvate as starter substrates.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (29 results)

All 2018 2017 2016 2015 Other

All Journal Article (9 results) (of which Peer Reviewed: 8 results,  Open Access: 1 results,  Acknowledgement Compliant: 4 results) Presentation (18 results) (of which Int'l Joint Research: 7 results,  Invited: 7 results) Remarks (2 results)

  • [Journal Article] Peptide Epimerization Machineries Found in Microorganisms2018

    • Author(s)
      Ogasawara Yasushi、Dairi Tohru
    • Journal Title

      Front. Microbiol.

      Volume: 9 Pages: 1-9

    • DOI

      10.3389/fmicb.2018.00156

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Functional analysis of methyltransferases participating in streptothricin-related antibiotic biosynthesis2018

    • Author(s)
      Niikura Haruka、Maruyama Chitose、Ogasawara Yasushi、Shin-ya Kazuo、Dairi Tohru、Hamano Yoshimitsu
    • Journal Title

      J. Biosci. Bioeng.

      Volume: 125 Issue: 2 Pages: 148-154

    • DOI

      10.1016/j.jbiosc.2017.09.004

    • NAID

      40021471176

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 放線菌が生み出した疑似ペプチド化合物-疑似ペプチド(ケトメミシン)がもつカルボニルメチレンの生合成を解明-2018

    • Author(s)
      小笠原泰志, 大利 徹
    • Journal Title

      化学と生物

      Volume: 56 Pages: 76-78

    • NAID

      130007563335

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Biosynthesis of Oligopeptides Using ATP-Grasp Enzymes2017

    • Author(s)
      Ogasawara Yasushi、Dairi Tohru
    • Journal Title

      Chemistry

      Volume: 23 Issue: 45 Pages: 10714-10724

    • DOI

      10.1002/chem.201700674

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biosynthesis of the Carbonylmethylene Structure Found in the Ketomemicin Class of Pseudotripeptides2017

    • Author(s)
      J. Kawata, T. Naoe, Y. Ogasawara, and T. Dairi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 8 Pages: 2026-2029

    • DOI

      10.1002/anie.201611005

    • NAID

      120006383813

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Exploring peptide ligase orthologs in actinobacteria-discovery of pseudopeptide natural products, ketomemicins-2016

    • Author(s)
      Y. Ogasawara, J. Kawata, M. Noike, Y. Satoh, K. Furihata, and T. Dairi
    • Journal Title

      ACS Chem. Biol.

      Volume: 11 Issue: 6 Pages: 1686-1692

    • DOI

      10.1021/acschembio.6b00046

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Characterization of three amidinotransferases involved in the biosynthesis of ketomemicins2016

    • Author(s)
      Y. Ogasawara, M. Fujimori, J. Kawata, and T. Dairi
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 26 Issue: 15 Pages: 3662-3664

    • DOI

      10.1016/j.bmcl.2016.05.090

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structure and activity relationships of the anti-Mycobacterium antibiotics resorcinomycin and pheganomycin2016

    • Author(s)
      Y. Ogasawara, K. Ooya, M. Fujimori, M. Noike, and T. Dairi
    • Journal Title

      J. Antibiot.

      Volume: 69 Issue: 2 Pages: 119-120

    • DOI

      10.1038/ja.2015.88

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Identification and analysis of the resorcinomycin biosynthetic gene cluster.2015

    • Author(s)
      K. Ooya, Y. Ogasawara, M. Noike, and T. Dairi
    • Journal Title

      Biosci. Biotechnol. Biochem

      Volume: 79 Issue: 11 Pages: 1833-1837

    • DOI

      10.1080/09168451.2015.1050992

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Presentation] カルボニルメチレン構造を有するシュードトリペプチド(Ketomemicin)の生合成機構2018

    • Author(s)
      大利 徹
    • Organizer
      2018年度日本農芸化学会大会シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Exploring Novel Peptide Ligase Orthologs-Discovery and Biosynthetic Studies of Carbonylmethylene-Containing Pseudotripeptides Ketomemicins-2017

    • Author(s)
      Y. Ogasawara, J. Kawata, T. Naoe, M. Fujimori, M. Noike and T. Dairi
    • Organizer
      Directing Biosynthesis V
    • Place of Presentation
      Warwick Univ (United Kingdom)
    • Year and Date
      2017-03-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ケトメミシンの生合成に関わるアミジノ基転移酵素の機能解析2017

    • Author(s)
      小笠原 泰志、藤盛 道子、川田 純平、大利 徹
    • Organizer
      2017年度日本農芸化学会大会
    • Place of Presentation
      京都女子大学(京都府・京都市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Biosynthesis of the Carbonylmethylene Containing Pseudopeptides, Ketomemicins2017

    • Author(s)
      Y. Ogasawara, J. Kawata, T. Naoe, M. Fujimori, and T. Dairi
    • Organizer
      US-Japan Seminar on the Biosynthesis of Natural Products for Young Researchers
    • Place of Presentation
      東京工業大学(東京都・目黒区)
    • Year and Date
      2017-03-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ケトメミシンにみられるカルボニルメチレン型シュードペプチドの生合成2017

    • Author(s)
      直江 大樹, 川田 純平, 小笠原 泰志, 大利 徹
    • Organizer
      生合成リデザイン第1回若手シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] New enzymes for biosynthesis of ketomemicin, a pseudotripeptide with carbonylmethylene structure2016

    • Author(s)
      Y. Ogasawara, J. Kawata, and T. Dairi
    • Organizer
      5th International Conference on Novel Enzymes
    • Place of Presentation
      Hampshire Hotel- Plaza Groningen (Netherlands)
    • Year and Date
      2016-10-11
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] カルボニルメチレン構造を持つシュードトリペプチド(ケトメミシン)の発見と酵素的全合成2016

    • Author(s)
      小笠原 泰志、川田 純平、野池 基義、藤盛 道子、佐藤 康治、降旗 一夫、大利 徹
    • Organizer
      第58回天然有機化合物討論会
    • Place of Presentation
      東北大学(宮城県・仙台市)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] ケトメミシンにみられるシュードペプチド部の生合成解析2016

    • Author(s)
      川田 純平、直江 大樹、小笠原 泰志、大利 徹
    • Organizer
      2016年度、日本放線菌学会大会
    • Place of Presentation
      東京大学(東京都・文京区)
    • Year and Date
      2016-09-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] Exploring peptide ligase orthologs in actinobacteria2016

    • Author(s)
      Y. Ogasawara, J. Kawata, M. Noike, Y. Satoh, K. Furihata, and T. Dairi
    • Organizer
      The Fifth International Conference on Cofactors (ICC-05) and Active Enzyme Molecule 2016 (AEM 2016)
    • Place of Presentation
      宇奈月国際会館(富山県・黒部市)
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] フェガノマイシン、レゾルシノマイシン類抗生物質の構造活性相関2016

    • Author(s)
      小笠原 泰志、藤盛 道子、雄谷 洸一、野池 基義、大利 徹
    • Organizer
      2016年度日本農芸化学会大会
    • Place of Presentation
      札幌コンベンションセンター(北海道・札幌市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] 微生物に見出されたペプチドリガーゼオルソログノ機能解析2016

    • Author(s)
      小笠原 泰志、河田純平、佐藤康治、降旗一夫、大利 徹
    • Organizer
      2016年度日本農芸化学会大会
    • Place of Presentation
      札幌コンベンションセンター(北海道・札幌市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Peptide synthesis cooperatively achieved by peptide ligase and ribosomes2015

    • Author(s)
      Tohru Dairi
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Sheraton Waikiki, Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 放線菌の新規ペプチドリガーゼ2015

    • Author(s)
      大利 徹
    • Organizer
      第88回日本生化学会大会シンポジウム
    • Place of Presentation
      神戸ポートアイランド(兵庫県・神戸市)
    • Year and Date
      2015-12-01
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 放線菌に見いだされた新規ペプチドライゲースオルソログの機能解析2015

    • Author(s)
      重松 真由子,小笠原 泰志,大利 徹
    • Organizer
      2015年度日本農芸化学会北海道支部大会
    • Place of Presentation
      北海道大学(北海道・札幌市)
    • Year and Date
      2015-11-14
    • Related Report
      2015 Annual Research Report
  • [Presentation] 放線菌に見出したATP-grasp-ligaseが触媒する多様なアミド形成反応2015

    • Author(s)
      大利 徹
    • Organizer
      第67回日本生物工学会大会シンポジウム
    • Place of Presentation
      城山観光ホテル(鹿児島県・鹿児島市)
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] A novel enzyme capping N-terminus of various peptides with amidino-PheGly derivatives2015

    • Author(s)
      Tohru Dairi
    • Organizer
      2nd European Conference on Natural Products
    • Place of Presentation
      Goethe-Universität, Frankfurt/Main (Germany)
    • Year and Date
      2015-09-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Exploring Novel Peptide Ligase Orthologs in Actinobacteria2015

    • Author(s)
      Y. Ogasawara, J. Kawata, M. Noike, K. Furihata and T. Dairi
    • Organizer
      2nd European Conference on Natural Products
    • Place of Presentation
      Goethe-Universität, Frankfurt/Main (Germany)
    • Year and Date
      2015-09-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A novel enzyme capping N-terminus of various peptides with amidino-PheGly derivatives2015

    • Author(s)
      Tohru Dairi
    • Organizer
      42nd International Symposium & Annual Meeting (The Korean Society for Microbiology and Biotechnology)
    • Place of Presentation
      Hwabaek International Convention Center, Gyeongju, Korea
    • Year and Date
      2015-06-25
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Remarks] 多様なペプチドのアミノ末端をキャッピングする酵素を発見

    • URL

      https://www.hokudai.ac.jp/news/141125_pr_eng.pdf

    • Related Report
      2017 Annual Research Report
  • [Remarks] 北海道大学大学院 工学研究院 応用生物化学研究室ホームページ

    • URL

      http://www.eng.hokudai.ac.jp/labo/tre/ABCLab_jp/

    • Related Report
      2015 Annual Research Report

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Published: 2015-04-16   Modified: 2019-03-29  

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