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Study on post-translational isoprenylation of a tryptophan residue in quorum sensing pheromone

Research Project

Project/Area Number 24688011
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionThe University of Tokyo (2014-2016)
Chubu University (2012-2013)

Principal Investigator

Okada Masahiro  東京大学, 薬学研究科(研究院), 准教授 (40377792)

Project Period (FY) 2012-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥27,170,000 (Direct Cost: ¥20,900,000、Indirect Cost: ¥6,270,000)
Fiscal Year 2015: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2014: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2013: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2012: ¥14,300,000 (Direct Cost: ¥11,000,000、Indirect Cost: ¥3,300,000)
Keywordsクオラムセンシング / 翻訳後修飾 / 枯草菌 / トリプトファン / イソプレニル化 / フェロモン
Outline of Final Research Achievements

Post-translational isoprenylation of a tryptophan residue was first found in a prokaryotes Bacillus subtilis. In order to evaluate the diversity of post-translational isoprenylation, we focused on the modification enzymes. Based on the information of the essential amino acid residues for the isoprenylation activity, a novel Trp-farnesyltransferase and a novel Trp-farnesylated peptide were found in another phyla of bacteria. Then, X-ray crystal analysis of the Trp-farnesyltransferase was carried out, and then genome mining for proteins sharing the structural features of the enzyme revealed that post-translational isoprenylation of tryptophan was widely distributed in several phyla of bacteria.
In addition, a novel Trp-farnesylated peptide involved in the formation of sticky biofilm was found from B. subtilis subsp. natto. Then, detailed farnesylation analyses of the enzyme revealed that post-translationally isoprenylating enzyme for Trp residue exhibited broad substrate tolerance.

Report

(6 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (27 results)

All 2017 2016 2015 2014 2012 Other

All Journal Article (15 results) (of which Peer Reviewed: 15 results,  Open Access: 7 results,  Acknowledgement Compliant: 12 results) Presentation (12 results) (of which Int'l Joint Research: 3 results,  Invited: 10 results)

  • [Journal Article] Posttranslational isoprenylation of tryptophan in bacteria2017

    • Author(s)
      Masahiro Okada, Tomotoshi Sugita, Ikuro Abe
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 13 Pages: 338-346

    • DOI

      10.3762/bjoc.13.37

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Characterization of giant modular PKSs provides insight into genetic mechanism for structural diversification of aminopolyol polyketides2017

    • Author(s)
      Zhang, L., Hashimoto, T., Qin, B., Hashimoto, J., Kozone, I., Kawahara, T., Okada, M., Awakawa, T., Ito, T., Asakawa, Y., Ueki, M., Takahashi, S., Osada, H., Wakimoto, T., Ikeda, H., Shin-ya, K., Abe, I.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 7 Pages: 1740-1745

    • DOI

      10.1002/anie.201611371

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Stereospecific prenylation of tryptophan by a cyanobacterial post-translational modification enzyme2016

    • Author(s)
      Okada, M., Sugita, T., Akita, K., Nakashima, Y., Tian, T., Li, C., Mori, T., Abe, I.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 40 Pages: 9639-9644

    • DOI

      10.1039/c6ob01759b

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Genome-based discovery of an unprecedented cyclization mode in fungal sesterterpenoids biosynthesis2016

    • Author(s)
      Okada, M., Matsuda, Y., Mitsuhashi, T., Hoshino, S., Mori, T., Nakagawa, K., Quan, Z., Qin, B., Zhang, H., Hayashi, F., Kawaide, H., Abe, I.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 31 Pages: 10011-10018

    • DOI

      10.1021/jacs.6b05799

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Astellifadiene: Structure Determination by NMR Spectroscopy and Crystalline Sponge Method, and Elucidation of its Biosynthesis2016

    • Author(s)
      Matsuda, Y., Mitsuhashi,T., Lee, S., Hoshino, M., Mori, T., Okada, M., Zhang, H., Hayashi, F., Fujita, M., Abe, I.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 19 Pages: 5785

    • DOI

      10.1002/anie.201601448

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Effective production of aromatic polyketides in Streptomyces bacteria using combined-culture2016

    • Author(s)
      Shotaro Hoshino, Masahiro Okada, Hiroyasu Onaka, Ikuro Abe.
    • Journal Title

      Nat. Prod. Commun.

      Volume: 11 Pages: 979-981

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Manipulation of prenylation reactions by structure-based engineering of bacterial indolactam prenyltransferases2016

    • Author(s)
      T. Mori, L. Zhang, T. Awakawa, S. Hoshino, M. Okada, H. Morita, I. Abe
    • Journal Title

      Nature Communications

      Volume: 7 Issue: 1 Pages: 10849-10851

    • DOI

      10.1038/ncomms10849

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] An unusual chimeric diterpene synthase from Emericella varicolor and its functional conversion into a sesterterpene synthase by domain swapping2016

    • Author(s)
      B. Qin, Y. Matsuda, T. Mori, M. Okada, Z. Quan, T. Mitsuhashi, T. Wakimoto, I. Abe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 5 Pages: 1658-1661

    • DOI

      10.1002/anie.201509263

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Chemical Structure and Biological Activity of a Quorum Sensing Pheromone from Bacillus subtilis subsp. natto.2015

    • Author(s)
      M. Okada, Y. Nakamura, S. Hayashi, K. Ozaki, and S. Usami.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 25 Issue: 19 Pages: 4293-4296

    • DOI

      10.1016/j.bmcl.2015.07.083

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Dietziamides, novel tetramic acid dimers from Dietzia timorensis MZ-3 with antioxidative activity2015

    • Author(s)
      S. Hoshino, T. Wakimoto, H. Zhang, F. Hayashi, M. Okada, I. Abe
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 25 Issue: 18 Pages: 3953-3955

    • DOI

      10.1016/j.bmcl.2015.07.035

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Niizalactams A-C, multicyclic macrolactams isolated from combined culture of Streptomyces with mycolic acid-containing bacterium2015

    • Author(s)
      S. Hoshino, M. Okada, T. Wakimoto, H. Zhang, F. Hayashi, H. Onaka, I. Abe
    • Journal Title

      J. Nat. Prod.

      Volume: 78 Issue: 12 Pages: 3011-3017

    • DOI

      10.1021/acs.jnatprod.5b00804

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Identification of a quorum sensing pheromone posttranslationally farnesylated at the internal tryptophan residue from Bacillus subtilis subsp. natto2015

    • Author(s)
      Shunsuke Hayashi, Syohei Usami, Yuta Nakamura, Koki Ozaki, Masahiro Okada
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: 79 Issue: 10 Pages: 1567-1569

    • DOI

      10.1080/09168451.2015.1032884

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A region corresponding to second aspartate-rich motif in tryptophan isoprenylating enzyme, ComQ, serves as a substrate-binding site.2014

    • Author(s)
      M. Okada, A. Ishihara, R. Yamasaki, F. Tsuji, S. Hayashi, S. Usami, and Y. Sakagami.
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 印刷中 Issue: 4 Pages: 550-555

    • DOI

      10.1080/09168451.2014.891932

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Lack of the Consensus Sequence Necessary for Tryptophan Prenylation in the ComX Pheromone Precursor2012

    • Author(s)
      F. Tsuji, A. Ishihara, A. Nakagawa, M. Okada, S. Kitamura, K. Kanamaru, Y. Masuda, K. Murakami, K. Irie, and Y. Sakagami.
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 76 Issue: 8 Pages: 1492-1496

    • DOI

      10.1271/bbb.120206

    • NAID

      10031065914

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Creation of pure nanodrugs and their anticancer properties2012

    • Author(s)
      H. Kasai, T. Murakami, Y. Ikuta, Y. Koseki, K. Baba, H. Oikawa, H. Nakanishi, M. Okada, M. Shoji, M. Ueda, H. Imahori, M. Hashida
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Issue: 41 Pages: 10315-10318

    • DOI

      10.1002/anie.201204596

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] Post-translational prenylation of tryptophan.2017

    • Author(s)
      Masahiro Okada
    • Organizer
      日本化学会第97春季年会 International Symposium on Molecular Science
    • Place of Presentation
      慶應義塾大学 (神奈川県, 横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 翻訳後修飾によるトリプトファンのイソプレニル化2017

    • Author(s)
      岡田 正弘
    • Organizer
      高分子・ハイブリッド材料研究センター (PHyM) 若手フォーラム
    • Place of Presentation
      東北大学 (宮城県, 仙台市)
    • Year and Date
      2017-02-27
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 翻訳後修飾によるトリプトファンのイソプレニル化2016

    • Author(s)
      岡田 正弘
    • Organizer
      第78回講演会 有機化学研究会(白鷺セミナー)
    • Place of Presentation
      大阪府立大学 (大阪府, 堺市)
    • Year and Date
      2016-12-06
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Post-translational prenylation of a tryptophan residue in quorum sensing pheromones.2016

    • Author(s)
      Masahiro Okada
    • Organizer
      1st International Conference on Advance Pharmacy and Pharmaceutical Sciences (ICAPPS)
    • Place of Presentation
      Universitas Indonesia, Depok, Jakarta, Indonesia.
    • Year and Date
      2016-10-21
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 翻訳後修飾によるトリプトファンのイソプレニル化2016

    • Author(s)
      岡田 正弘
    • Organizer
      日本農芸化学会関東支部2016年度例会
    • Place of Presentation
      東京農業大学 (東京都, 世田谷区)
    • Year and Date
      2016-06-25
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Post-Translational Isoprenylation of Tryptophan2015

    • Author(s)
      M. Okada
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-20
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Post-Translational Isoprenylation of Tryptophan2015

    • Author(s)
      M. Okada
    • Organizer
      The Scripps Institution of Oceanography symposium
    • Place of Presentation
      San Diego, USA
    • Year and Date
      2015-07-31
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 納豆菌由来のComXフェロモンの解明2015

    • Author(s)
      岡田正弘
    • Organizer
      生合成マシナリー第7回若手シンポジウム
    • Place of Presentation
      東京、東京工業大学
    • Year and Date
      2015-06-20
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] トリプトファンイソプレニルトランスフェラーゼのメカニズム解明とマシナリーの構築. 生合成マシナリー第6回若手シンポジウム2014

    • Author(s)
      岡田正弘
    • Organizer
      生合成マシナリー第6回若手シンポジウム
    • Place of Presentation
      東京、東京大学
    • Year and Date
      2014-08-06
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] トリプトファンイソプレニルトランスフェラーゼのメカニズム解明とマシナリーの構築. 生合成マシナリー第6回若手シンポジウム2014

    • Author(s)
      岡田正弘
    • Organizer
      生合成マシナリー第7回公開シンポジウム
    • Place of Presentation
      東京、東京大学
    • Year and Date
      2014-06-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Peptide isoprenylation2012

    • Author(s)
      M. Okada.
    • Organizer
      International Symposiumon Natural Products Chemistry and Chemical Biology 2012
    • Place of Presentation
      Hangzhou, China
    • Related Report
      2012 Annual Research Report
  • [Presentation] 翻訳後修飾によりトリプトファンがイソプレニル化された新規ペプチドの探索

    • Author(s)
      宇佐美 翔平、林 峻輔、中村 優太、岡田 正弘
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      神奈川, 明治大学
    • Related Report
      2013 Annual Research Report

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

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