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Design, syntheses and diagnostic applications of beta(1-6)-linked glycolipids (GGLs) as the major cell membrane components of Mycoplasma pneumoniae

Research Project

Project/Area Number 25450146
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionChiba University

Principal Investigator

NISHIDA Yoshihiro  千葉大学, 融合科学研究科(研究院), 教授 (80183896)

Research Collaborator MATSUDA Kazuhiro  エムバイオテック株式会社
MATSUDA Sachie  エムバイオテック株式会社
YUAN Mengfei  千葉大学, 大学院融合科学研究科, 博士課程
FUKUDA Kazuo  千葉大学, 大学院融合科学研究科, 博士課程
TANAKA Daiki  千葉大学, 大学院融合科学研究科, 博士課程
DOHI Hirofumi  千葉大学, 大学院融合科学研究科, 准教授
UZAWA Hirotaka  産業技術総合研究所, ナノシステム研究部門, 主任研究員
MIZUNO Mamoru  公益財団法人野口研究所, 糖鎖有機化学研究室, 室長
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords糖鎖 / マイコプラズマ / 感染診断 / 細胞膜 / 糖脂質 / グリコシル化反応 / 三次元構造 / 脂質抗原 / NMRスペクトル / 細胞膜構造 / 重水素標識化 / 診断プローブ / 糖鎖合成 / グリセロ糖脂質 / フルオラス合成法 / 肺炎マイコプラズマ / NMR解析 / 立体配座 / リン脂質
Outline of Final Research Achievements

Mycoplasma is one of the simplest bacteria having no rigid cell walls and lipopolysaccharides (LPS). Instead, they utilize either alpha- or beta-glycolipids in cytoplasmic membrane. Also in our preceding studies, we have reported alpha-glycolipid antigens (GGPLs) in M. fermentans as well as beta-linked ones (GGLs)in M. pneumoniae. In the present study, we applied our glycosylation methods for the library assembly of GGLs homologues carrying variable acyl chains and examined their chemical behaviors. The chemical library involved a deuterium labeled GGL homologue for simultaneous MS detection of natural GGLs. It involved also an acetyl (C2) homologue for the study on molecular dynamics (MD). The assembled chemical library enabled us to elucidate the best GGLs homologue (GGLS C18) for the ELISA diagnosis of Mycoplasma pneumoniae infection and their possibility to make a crown ether-like ionophore around the non-reducing terminal end in their dynamic three dimensional (3D) structures.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (26 results)

All 2015 2014 2013

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 7 results,  Acknowledgement Compliant: 7 results) Presentation (15 results) Book (2 results)

  • [Journal Article] Comparative analyses of helical properties in asymmetric 1,2-diacyl-sn-glycerols by means of circular dichroism and proton NMR spectroscopy: Notable effects of substituting groups at sn-3 position2015

    • Author(s)
      Mengfei Yuan, Kazuo Fukuda, Hirofumi Dohi, Hirotaka Uzawa, Yoshihiro Nishida
    • Journal Title

      Tetrahedron Asymmetry,

      Volume: 26 Issue: 20 Pages: 1138-1144

    • DOI

      10.1016/j.tetasy.2015.08.012

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A recyclable heavy fluorous tag carrying an allyl alcohol pendant group: Design and evaluation toward applications in synthetic carbohydrate chemistry2015

    • Author(s)
      Kazuo Fukuda, Mami Tojino, Kohtaro Goto, Hirofumi Dohi, Yoshihiro Nishida, Mamoru Mizuno
    • Journal Title

      Carbohydrate Research

      Volume: 407 Pages: 122-130

    • DOI

      10.1016/j.carres.2015.02.002

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family2014

    • Author(s)
      Hirofumi Dohi, Takeru Kanazawa, Akihiro Saito, Keita Sato, Hirotaka Uzawa, Yasuo Seto and Yoshihiro Nishida
    • Journal Title

      Beilstein J. Organic Chemistry

      Volume: 10 Pages: 1504-1512

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Interaction of 70-kDa heat shock protein with glycosaminoglycans and acidic glycopolymers2014

    • Author(s)
      Yoichiro Harada, Estelle Garenaux, Takehiro Nagatsuka, Hirotaka Uzawa, Yoshihiro Nishida, Chihiro Sato, Ken Kitajima
    • Journal Title

      Biochem. Biophys. Res. Communication

      Volume: 453 Issue: 2 Pages: 229-234

    • DOI

      10.1016/j.bbrc.2014.05.137

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Preparation of acid-resistant heavy fluorous tags for recycling in synthetic systems2014

    • Author(s)
      Kazuo Fukuda, Mami Tojino, Kohtaro Goto, Hirofumi Dohi, Yoshihiro Nishida, Mamoru Mizuno
    • Journal Title

      J. Fluorine Chemistry

      Volume: 166 Pages: 52-59

    • DOI

      10.1016/j.jfluchem.2014.07.014

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Molecular Design and Synthesis of Novel Salicyl Glycoconjugates as Elicitors against Plant Diseases2014

    • Author(s)
      Zining Cui, Jun Ito, Hirofumi Dohi, Yoshimiki Amemiya, Yoshihiro Nishida
    • Journal Title

      PLOS ONE

      Volume: (9) e108338 Issue: 9 Pages: 1-9

    • DOI

      10.1371/journal.pone.0108338

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Odorless Access to Thioglycosides for Oligosaccharide Synthesis: Their Design and Advanced Procedures for Thioglycosidation2014

    • Author(s)
      Hirofumi Dohi, Yoshishiro Nishida
    • Journal Title

      Trends in Glycoscience and Glycotechnology

      Volume: 26 Issue: 151 Pages: 119-130

    • DOI

      10.4052/tigg.26.119

    • NAID

      130004841391

    • ISSN
      0915-7352, 1883-2113
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Design, Synthesis and Bioactivity of N-Glycosyl-N-(5-substituted phenyl-2-furoyl) Hydrazide Derivatives2014

    • Author(s)
      Zining Cui, Hang Su, Jiazhen Jiang, Xinling Yang, Yoshihiro
    • Journal Title

      International Journal of Molecular Sciences

      Volume: 15 Issue: 4 Pages: 6741-6756

    • DOI

      10.3390/ijms15046741

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Localized surface plasmon resonance detection of biological toxins using cell surface oligosaccharide on glyco chips2013

    • Author(s)
      T. Ngatsuka, H. Uzawa, K. Sato, S. Kondo、M. Izumi, K. Yokoyama, I. Ohsawa, Y. Seto, P. Neri, H. Mori. Y. Nishida, M. Saito, E. Tamiya
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 5 Pages: 4173-4180

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 質量分析法を用いたマイコプラズマ糖脂質抗原検出2015

    • Author(s)
      福田和男、宮地彬、松田幸枝、土肥博史、松田和洋、西田芳弘
    • Organizer
      GlycoTokyo 2015
    • Place of Presentation
      慶応義塾大学 矢上キャンパス
    • Year and Date
      2015-10-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 糖コレステロール誘導体の簡便合成法の検討2015

    • Author(s)
      大山加南、板垣恵那、土肥博史、西田芳弘、鵜沢浩隆
    • Organizer
      GlycoTokyo 2015
    • Place of Presentation
      慶応義塾大学 矢上キャンパス
    • Year and Date
      2015-10-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthetic Glycolipid Antigens (GGPLS and GGLs) for diagnosis of Mycoplasma infection diseases (MIDs)2015

    • Author(s)
      Mengfei Yuan, Kazuo Fukuda, Yoshihiro Nishida, Sachie Matsuda, Kazuhiro Matsuda
    • Organizer
      第34回 日本糖質学会年会
    • Place of Presentation
      東京大学安田記念講堂
    • Year and Date
      2015-07-31
    • Related Report
      2015 Annual Research Report
  • [Presentation] 安定同位体標識を利用したマイコプラズマ糖脂質抗原検出2015

    • Author(s)
      福田和男、袁 夢飛、松田幸枝、土肥博史、水野真盛、松田和洋、西田芳弘
    • Organizer
      第34回 日本糖質学会年会
    • Place of Presentation
      東京大学 安田記念講堂
    • Year and Date
      2015-07-31
    • Related Report
      2015 Annual Research Report
  • [Presentation] 生物毒素の高感度検出を指向した糖鎖修飾窒化ケイ素チップの開発2015

    • Author(s)
      田中大輝、鵜沢浩隆、永塚健宏、大場雄貴、瀬戸康雄、吉田敏雄、土肥博史、西田芳弘
    • Organizer
      第34回 日本糖質学会年会
    • Place of Presentation
      東京大学 安田記念講堂
    • Year and Date
      2015-07-31
    • Related Report
      2015 Annual Research Report
  • [Presentation] アリル型ヘビーフルオラスタグの合成と応用2015

    • Author(s)
      福田和男、戸治野真美、後藤浩太朗、土肥博史、西田芳弘、水野真盛
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋 (日本大学)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] pNP ガラクトフラノシド、ピラノシドのワンセット合成2014

    • Author(s)
      中島政哉、朝日勇気、高靖麗宇、大山加南、土肥博史、西田芳弘
    • Organizer
      GlycoTOKYO 2014
    • Place of Presentation
      松戸 (千葉大学)
    • Year and Date
      2014-11-08
    • Related Report
      2014 Research-status Report
  • [Presentation] Sugar modified silicon nitride chips for the detection of biological toxins2014

    • Author(s)
      田中大輝、鵜沢浩隆、永塚健宏、吉田敏雄、土肥博史、西田芳弘
    • Organizer
      Glyco TOKYO 2014
    • Place of Presentation
      松戸 (千葉大学)
    • Year and Date
      2014-11-08
    • Related Report
      2014 Research-status Report
  • [Presentation] 炭素–炭素結合型ヘビーフルオラスタグの開発と糖鎖合成への応用2014

    • Author(s)
      福田和男、戸治野真美、後藤浩太朗、土肥博史、西田芳弘、水野真盛
    • Organizer
      第1回 FCCAシンポジウム/FCCAグライコサイエンス若手フォーラム
    • Place of Presentation
      名古屋 (名古屋大学)
    • Year and Date
      2014-08-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 炭素–炭素結合型ヘビーフルオラスタグを利用した糖鎖合成2014

    • Author(s)
      福田和男、戸治野真美、後藤浩太朗、土肥博史、西田芳弘、水野真盛
    • Organizer
      第33回 日本糖質学会年会
    • Place of Presentation
      名古屋 (名古屋大学)
    • Year and Date
      2014-08-10 – 2014-08-12
    • Related Report
      2014 Research-status Report
  • [Presentation] Conformational properties of alpha and beta-glycolipids as Mycoplasma cytoplasmic-membrane components2013

    • Author(s)
      Mengfei Yuan, Ryoko Matsunaga, Hirofumi Dohi, Sachie Matsuda, Kazuhiro Matsuda, Yoshihiro Nishida
    • Organizer
      XXII International Symposium on Glycoconjugates
    • Place of Presentation
      Dalian、China
    • Related Report
      2013 Research-status Report
  • [Presentation] 肺炎マイコプラズマに由来する糖脂質抗原の合成研究2013

    • Author(s)
      土肥博史、尾山知絵、松田幸枝、松田和洋、西田芳弘
    • Organizer
      第32回日本糖質学会年会
    • Place of Presentation
      大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] 糖を分子基盤とする植物病害抵抗性誘導剤の開発研究2013

    • Author(s)
      崔紫寧、土肥博史、伊藤潤、雨宮良幹、西田芳弘
    • Organizer
      第32回日本糖質学会年会
    • Place of Presentation
      大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] 6-リン酸化マンノースコンジュゲートの合成研究2013

    • Author(s)
      山本和平、熊﨑りえ、土肥博史、西田芳弘
    • Organizer
      GlycoTOKYO 2013
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] ラクトース合成酵素の基質認識機構に基づくエンコード酵素合成法2013

    • Author(s)
      高橋ほのか、竹田真由美、土肥博史、西田芳弘
    • Organizer
      GlycoTOKYO 2013
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Book] 炭水化物 (糖質) (新版 基礎食品学の第2章)2015

    • Author(s)
      西田芳弘
    • Publisher
      アイ・ケイ コーポレーション
    • Related Report
      2015 Annual Research Report
  • [Book] マイクロナノカプセルの調製、徐放性制御と応用例、第16節 page 80-87 「グライコナノカプセルの調製と機能評価」2014

    • Author(s)
      西田芳弘、土肥博史
    • Total Pages
      510
    • Publisher
      技術情報協会編
    • Related Report
      2014 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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