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2011 Fiscal Year Final Research Report

Elucidation of reaction mechanism of novel biosynthetic enzymes for derivatization of reveromycin

Research Project

  • PDF
Project/Area Number 21580104
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Applied microbiology
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

TAKAHASHI Shunji  独立行政法人理化学研究所, 化学情報・化合物創製チーム, チームヘッド (30311608)

Project Period (FY) 2009 – 2011
Keywords放線菌 / 天然化合物 / ポリケチド / リベロマイシンA / スピロアセタール化合物 / 生合成
Research Abstract

We disrupted reveromycin biosynthetic gene cluster and analyzed the structure of biosynthetic intermediates isolated from each disruptant. We identified various reveromycin derivatives required for the speculation of its biosynthetic pathway. Moreover, the analysis of biosynthetic mechanisms using RM-A1a(triol intermediate) and recombinant enzymes resulted in the identification of dihydroxy ketone synthase(RevG) and spiroacetal synthase(RevJ), which are involved in stereospecific spiroacetal formation.

  • Research Products

    (44 results)

All 2012 2011 2010 2009 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (25 results) Book (4 results) Remarks (2 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Spirotoamides A and B, novel 6, 6-spiroacetal polyketides isolated from a microbial metabolite fraction library2012

    • Author(s)
      Nogawa T., Takahashi S., Okano A., Kawatani M., Uramoto M., Saito T., and Osada H
    • Journal Title

      J. Antibiot

      Volume: 65(3) Pages: 123-128

    • Peer Reviewed
  • [Journal Article] Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation2011

    • Author(s)
      Takahashi S, Toyoda A, Sekiyama Y, Takagi H, Nogawa T, Uramoto M, Suzuki R, Koshino H, Kumano T, Panthee S, Dairi T, Ishikawa J, Ikeda H, Sakaki Y, and Osada H
    • Journal Title

      Nat. Chem. Biol

      Volume: 7 Pages: 461-468

    • Peer Reviewed
  • [Journal Article] Gene disruption and biochemical characterization of verruculogen synthase of Aspergillus fumigates2011

    • Author(s)
      Kato N, Suzuki H, Takagi H, Uramoto M, Takahashi S., and Osada H
    • Journal Title

      Chembiochem

      Volume: 12(5) Pages: 711-714

    • Peer Reviewed
  • [Journal Article] Genetic safeguard against mycotoxin cyclopiazonic acid production in Aspergillus oryzae2011

    • Author(s)
      Kato N., Tokuoka M., Shinohara Y., Kawatani M., Uramoto M., Seshime Y., Fujii I., Kitamoto K., Takahashi T., Takahashi S., Koyama Y., and Osada H
    • Journal Title

      Chembiochem

      Volume: 12(9) Pages: 1376-1382

    • Peer Reviewed
  • [Journal Article] Improvement of transformation efficiency by strategic circumvention of restriction barriers in Streptomyces griseus2011

    • Author(s)
      Suzuki H, Takahashi S, Osada H, and Yoshida K
    • Journal Title

      J. Microbiol. Biotechnol

      Volume: 21(7) Pages: 675-678

    • Peer Reviewed
  • [Journal Article] Furaquinocins I and J : Novel polyketide isoprenoid hybrid compounds from Streptomyces reveromyceticus SN-5932011

    • Author(s)
      Panthee S, Takahashi S, Takagi H, Nogawa T, Oowada E, Uramoto M, and Osada H
    • Journal Title

      J. Antibiot

      Volume: 64(7) Pages: 509-513

    • Peer Reviewed
  • [Journal Article] Detection of cytochrome P450 substrates using small-molecule droplet array on NADH-immobilized solid surface2011

    • Author(s)
      Takayama H, Takahashi S, Osada H, Iwabuchi Y, and Kanoh N
    • Journal Title

      Chembiochem

      Volume: 12(18) Pages: 2748-2752

    • Peer Reviewed
  • [Journal Article] Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-5932010

    • Author(s)
      Takahashi S., Takagi H., Toyoda A., Uramoto M., Nogawa T., Ueki M., Sakaki Y. and Osada H
    • Journal Title

      J. Bacteriol

      Volume: 192(11) Pages: 2839-2851

    • Peer Reviewed
  • [Journal Article] Verticilactam, a New Macrolactam isolated from a microbial metabolite fraction library2010

    • Author(s)
      Nogawa T., Okano A., Takahashi S., Uramoto M., Konno H., Saito T., and Osada H
    • Journal Title

      Org. Lett

      Volume: 12(20) Pages: 4564-4567

    • Peer Reviewed
  • [Journal Article] Molecular cloning and characterization of a broad substrate terpenoid oxidoreductase from Artemisia annua2010

    • Author(s)
      Ryden A. M., Ruyter-Spira C., Litjens R., Takahashi S., Quax W., Osada H., Bouwmeester H., Kayser O
    • Journal Title

      Plant Cell Physiol

      Volume: 51(7) Pages: 1219-1228

    • Peer Reviewed
  • [Journal Article] Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis2009

    • Author(s)
      Hashimoto M., Higuchi Y., Takahashi S., Osada H., Sakaki T., Toyomasu T., Sassa T., Kato N. and Dairi T
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 19(19) Pages: 5640-5643

    • Peer Reviewed
  • [Journal Article] Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus2009

    • Author(s)
      Kato N, Suzuki H, Takagi H, Asami Y, Kakeya H, Uramoto M, Usui T, Takahashi S., Sugimoto Y and Osada H
    • Journal Title

      Chembiochem

      Volume: 10(5) Pages: 920-928

    • Peer Reviewed
  • [Presentation] サクシニル化に関わるリベロマイシン生合成遺伝子の機能解析2012

    • Author(s)
      高橋俊二
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20120322-26
  • [Presentation] リベロマイシン生合成における多段階酵素反応の再構築2012

    • Author(s)
      熊野匠人
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20120322-26
  • [Presentation] 2-アルキルマロニル-CoA生合成機構の解析2012

    • Author(s)
      宮澤岳
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20120322-26
  • [Presentation] β-carboline compounds as biomediators of secondary metabolism in Streptomyces reveromyceticus2012

    • Author(s)
      Suresh Panthee
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20120322-26
  • [Presentation] Mechanism of 2-alkylmalonyl-CoA formation in reveromycin A biosynthesis2011

    • Author(s)
      Shunji Takahashi
    • Organizer
      16^<th> International Symposium on the Biology of Actinomycetes
    • Place of Presentation
      Puerto Vallarta, Mexico
    • Year and Date
      20111211-15
  • [Presentation] Biosynthetic Mechanism and Effective Production of Reveromycin A2011

    • Author(s)
      Hiroyuki Osada
    • Organizer
      16^<th> International Symposium on the Biology of Actinomycetes
    • Place of Presentation
      Puerto Vallarta, Mexico
    • Year and Date
      20111211-15
  • [Presentation] 微生物代謝産物フラクションライブラリーより単離した新規スピロアセタールポリケチド、スピロトアミドAおよびBの構造2011

    • Author(s)
      野川俊彦
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      20110927-29
  • [Presentation] Identification of key enzymes involved in spiroacetal formation in reveromycin A biosynthesis2011

    • Author(s)
      Shunji Takahashi
    • Organizer
      International union of microbiological societies(IUMS),放線菌学会共催
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      20110907-09
  • [Presentation] Analysis of 2-alkylmalonyl-CoA biosynthesis2011

    • Author(s)
      Takeshi Miyazawa
    • Organizer
      International union of microbiological societies(IUMS),放線菌学会共催
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      20110907-09
  • [Presentation] In vitro reconstruction of post-PKS modification in RM-A biosynthesis2011

    • Author(s)
      Takuto Kumano
    • Organizer
      International union of microbiological societies(IUMS),放線菌学会共催
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      20110907-09
  • [Presentation] Deciphering of reveromycin A biosynthesis and the production of novel derivatives2011

    • Author(s)
      Shunji Takahashi
    • Organizer
      International union of microbiological societies.(IUMS),放線菌学会共催
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      20110907-09
  • [Presentation] 遺伝子破壊によるリベロマイシン生合成機構の解析2011

    • Author(s)
      高橋俊二
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20110327-29
  • [Presentation] リベロマイシン生合成におけるバイヤー・ビリガー酸化反応解析2011

    • Author(s)
      熊野匠人
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20110327-29
  • [Presentation] ブチルマロニル-CoA生合成機構の解析2011

    • Author(s)
      宮澤岳
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20110327-29
  • [Presentation] Identification of biomediators that enhance reveromycin A production in Streptomyces reveromyceticus2011

    • Author(s)
      Suresh Panthee
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20110327-29
  • [Presentation] 分子内peroxide架橋形成を触媒するverruculogen合成酵素FtmFの機能解析・結晶化2011

    • Author(s)
      加藤直樹
    • Organizer
      日本農芸化学会
    • Place of Presentation
      京都女子大学
    • Year and Date
      20110327-29
  • [Presentation] リベロマイシンAのスピロアセタール環化機構の解析2010

    • Author(s)
      高橋俊二
    • Organizer
      日本放線菌学会
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      20100902-03
  • [Presentation] Development of screening system and identification of biomediators of reveromycin A biosynthesis2010

    • Author(s)
      Suresh Panthee
    • Organizer
      日本放線菌学会
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      20100902-03
  • [Presentation] リベロマイニンAスピロケタール生成に関わる新規デヒドロゲナーゼの機能解析2010

    • Author(s)
      高橋俊二
    • Organizer
      日本農芸化学会
    • Place of Presentation
      東京大学駒場
    • Year and Date
      20100327-30
  • [Presentation] リベロマイシン構造多様化に関わる2-アルキルマロニルCoA生合成機構の解析2010

    • Author(s)
      高木海
    • Organizer
      日本農芸化学会
    • Place of Presentation
      東京大学駒場
    • Year and Date
      20100327-30
  • [Presentation] Analysis of Reveromycin A Biosynthetic Gene Cluste2009

    • Author(s)
      Shunji Takahashi
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      20091215-20
  • [Presentation] Biochemical and crystal structure analyses of revenomycine E hydroxylase(P450RME) in reveromycin A biosynthetic gene cluster2009

    • Author(s)
      Shunji Takahashi
    • Organizer
      15th International Symposium on the Biology of Actinomycetes(ISBA' 15)
    • Place of Presentation
      Shanghai, China
    • Year and Date
      20090820-25
  • [Presentation] リベロマイシンAのスピロケタール生合成機構の解析2009

    • Author(s)
      高橋俊二
    • Organizer
      日本放線菌学会
    • Place of Presentation
      秋田ビューホテル
    • Year and Date
      20090716-17
  • [Presentation] Prenyltransferase from Streptomyces reveromyceticus2009

    • Author(s)
      Shunji Takahashi
    • Organizer
      TERPNET2009
    • Place of Presentation
      University of Tokyo
    • Year and Date
      20090525-29
  • [Presentation] リベロマイシンA生合成遺伝子クラスターの機能解析2009

    • Author(s)
      高橋俊二
    • Organizer
      第82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
    • Year and Date
      2009-10-21
  • [Book] 生物工学会誌2012

    • Author(s)
      高橋俊二
    • Total Pages
      95
  • [Book] バイオサイエンスとインダストリー2011

    • Author(s)
      高橋俊二、長田裕之
    • Total Pages
      486-487
  • [Book] 科学工業2011

    • Author(s)
      長田裕之、高橋俊二
    • Total Pages
      8-13
  • [Book] Comprehensive Natural Products II Chemistry and Biology2010

    • Author(s)
      Kuzuyama T., Hemmi H. and Takahashi S. L., Lui, H.-W
    • Total Pages
      493-516
  • [Remarks] 新聞掲載2011年06月06日化学工業日報2011年06月06日日経産業新聞

  • [Remarks] プレスリリース平成23年6月6日独立行政法人理化学研究所放線菌による「リベロマイシンA」生合成機序を遺伝子レベルで初めて解明-トマトエキスが誘導する放線菌遺伝子を探索し判明-ホームページ

    • URL

      http://www.riken.go.jp/r-world/research/lab/asi/cb-ccc/index.html

  • [Patent(Industrial Property Rights)] リベロマイシンAまたはその生合成中間体の製造法およびスピロケタール環含有化合物の製造方法2010

    • Inventor(s)
      長田裕之、高橋俊二、榊佳之、豊田敦
    • Industrial Property Rights Holder
      理化学研究所
    • Industrial Property Number
      特許、特願2010-194222
    • Filing Date
      2010-08-31

URL: 

Published: 2013-07-31  

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