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Synthesis and evaluation of sugar derivatives for developing the antimicrobial agent against H. pylori

Research Project

Project/Area Number 20550157
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionThe Noguchi Institute

Principal Investigator

YAMANOI Takashi  The Noguchi Institute, 研究部, 主任研究員 (20182595)

Co-Investigator(Kenkyū-buntansha) FUJITA Masaya  公益財団法人野口研究所, 研究部, 研究員 (20321672)
ODA Yoshiki  公益財団法人野口研究所, 研究部, 研究員 (00442567)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords抗ピロリ / ピロリ菌 / αGlcNAc / ステロイド / N-アセチル-グルコサミン / グリコシド / クラスター / 医薬品 / シクロデキストリン / 抗菌剤
Research Abstract

Aiming to develop the antimicrobial agent for H. pylori, a novel α-stereoselective glycosidation method of GlcNAc derivatives for producing the αGlcNAc glycosides has been successfully developed. This method was applicable to the productions of several kinds of αGlcNAc glycosides having a steroid structure, which led to the partial library construction of the αGlcNAc derivatives. In addition, the αGlcNAc assembly, which was expected to have a highly efficient antimicrobial activity toward H. pylori based on the sugar-cluster effect, was synthesized using cyclodextrin as a scaffolding molecule.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (46 results)

All 2011 2010 2009 2008 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (25 results) Remarks (3 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Glycoside hydrolase family 89 α-N-acetylglucosaminidase from clostridium perfringens specifically acts on GlcNAc 1,4Galβ1R at the non-reducing terminus of O-glycans in gastric mucin2011

    • Author(s)
      M.Fujita, A.Tsuchida, A.Hirata, N.Kobayashi, K.Goto, K.Osumi, Y.Hirose, J.Nakayama, T.Yamanoi, H.Ashida, M.Mizuno
    • Journal Title

      The Journal of Biological Chemistry 286巻

      Pages: 6479-6489

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Glycoside Hydrolase Family 89 a-N-acetylglucosaminidase from Clostridium perfringens Specifically Acts on GlcNAc 1, 4Ga1βIR at the Non-reducing Terminus of O-Glycans in Gastric Mucin2011

    • Author(s)
      藤田雅也、山ノ井孝
    • Journal Title

      The Journal of Biological Chemistry

      Volume: 286 Pages: 6479-6489

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A synthetic approach to anhydroketopyranoses having a 6,8-dioxabicyclo[3.2.1]octane structure from ketopyranoses2010

    • Author(s)
      T.Yamanoi, K.Matsumura, S.Matsuda, Y.Oda
    • Journal Title

      Heterocycles 82巻

      Pages: 531-542

    • NAID

      40017418851

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] L-Fruco- and D-psicofuranosylation reactions catalyzed by scandium triflate2010

    • Author(s)
      T.Yamanoi, T.Ishiyama, Y.Oda, S.Matsuda, M.Watanabe
    • Journal Title

      Heterocycles 81巻

      Pages: 1141-1147

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] L-Fructo-and D-Psicofuranosylation Reactions Catalyzed by Scandium Triflate2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Journal Title

      Heterocycles

      Volume: 81 Pages: 1141-1147

    • NAID

      40017082900

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ASYNTHETIC APPROACH TO ANHYDROKETOPYRANOSES HAVING A 6, 8-DIOXABICYCLO L3.2.1]OCTANE STRUCTURE FROM KETOPYR ANOSES2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Journal Title

      Heterocycles

      Volume: 82 Pages: 531-542

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Identification of the inclusion complexation between Phenyl β-D-(13C6)glucopyranoside and β -cyclodextrin using 2D 1H or 13C DOSY spectrum2009

    • Author(s)
      Y.Oda, S.Matsuda, T.Yamanoi, A.Murota, K.Katsuraya
    • Journal Title

      Supramolecualr Chemistry 21巻

      Pages: 638-642

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Identification of The Inclusion Complexation between Phenyl α-D-(^<13>C_6)-Glucopyranoside and α-Cyclodextrin using 2D ^1H or ^<13>C DOSY Spectrum2009

    • Author(s)
      Y.Oda, S.Matsuda, T.Yamanoi, A.Murota, K.Katsuraya
    • Journal Title

      Supramolecular Chemistry 21

      Pages: 638-642

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, synthesis and evaluation of D-galactose-β-cyclodextrin conjugates as drug-carrying molecules2008

    • Author(s)
      Y.Oda, H.Yanagisawa, M.Maruyama, K.Hattori, T.Yamanoi
    • Journal Title

      Bioorganic & Medicinal Chemistry 16巻

      Pages: 8830-8840

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a novel D-glucose-conjugated 15-crown-5 ether with a spiro ketal structure2008

    • Author(s)
      T.Yamanoi, Y.Oda, H.Muraishi, S.Matsuda
    • Journal Title

      Molecules 13巻

      Pages: 1840-1845

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of a partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A and of its analogs2008

    • Author(s)
      S.Matsuda, T.Yamanoi, M.Watanabe
    • Journal Title

      Tetrahedron 64巻

      Pages: 8082-8088

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of a partially benzylated derivative of the anhydro-D-altro-heptulose found in Coriaria japonica A and of its analogs2008

    • Author(s)
      S. Matsuda
    • Journal Title

      Tetrahedron 64

      Pages: 8082-8088

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure2008

    • Author(s)
      T. Yamanoi
    • Journal Title

      Molecules 13

      Pages: 1840-1845

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, synthesis and evaluation of D-galactose-β-cyclodextrin conjugates as drug-carrying molecules2008

    • Author(s)
      Y. Oda
    • Journal Title

      Bioorganic & Medicinal Chemistry 18

      Pages: 8830-8840

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Stereoselective formation of 1,2-cis-α-glycosidic linkages by glycosidation using 2-acetamido-2-deoxy-α-D-glucopyranos yl acetate derivatives2010

    • Author(s)
      T.Yamanoi, Y.Oda, W.Kaburagi, M.Midorikawa, K.Takahashi
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Syntheses of spirocompounds from 1-C-vinylated sugars2010

    • Author(s)
      T.Yamanoi, S.Matsuda,Y.Oda, A.Yoshida
    • Organizer
      The 2010International Chemical Congress of Pacific Basin Societies
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] Stereoselective formation of 1, 2-cis-a-glycosidic linkages by glycosidation using 2-acetamido-2-deoxy-a-D-glucopyranosyl acetate derivatives2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ハワイコンベンションセンター
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Syntheses of spirocompounds from 1-C-vinylated sugars2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ハワイコンベンションセンター
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis of fluorous crown ethers and their application to fluorous biphase organic reaction2010

    • Author(s)
      K.Koike, T.Yamanoi, Y.Oda, A.Yoshida, M.Watanabe
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Year and Date
      2010-12-18
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of Fluorous Crown Ethers and Their Application to Fluorous Biphase Organic Reaction2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      ハワイコンベンションセンター
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Bfp基結合型フルオラスクラウンエーテル類の合成と有機合成反応への利用2010

    • Author(s)
      山ノ井孝・小池健仁・小田慶喜・吉田彰宏・渡邊幹夫
    • Organizer
      第3回フルオラス科学研究会シンポジウム
    • Year and Date
      2010-10-08
    • Related Report
      2010 Final Research Report
  • [Presentation] Bfp基結合型フルオラスクラウンエーテル類の合成と有機合成反応への利用2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      第3回フルオラス科学研究会シンポジウム
    • Place of Presentation
      長良川国際会議場
    • Year and Date
      2010-10-08
    • Related Report
      2010 Annual Research Report
  • [Presentation] 包接に関与するプロトンを持たないゲスト分子のシクロデキストリン包接体のNMR解析2010

    • Author(s)
      山ノ井孝・小田慶喜・鬘谷要
    • Organizer
      第27回シクロデキストリンシンポジウム
    • Year and Date
      2010-09-07
    • Related Report
      2010 Final Research Report
  • [Presentation] 包接に関与するプロトンを持たないゲスト分子のシクロデキストリン包接体のNMR解析2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      第27回シクロデキストリンシンポジウム
    • Place of Presentation
      金沢市文化ホール
    • Year and Date
      2010-09-07
    • Related Report
      2010 Annual Research Report
  • [Presentation] Molecular interactions of concanavalin A lectin with phenyl glucoside derivatives using STD NMR spectra2010

    • Author(s)
      K.Katsuraya, Y.Oda, C.Kurosaki, S.Koshiba, T.Yamanoi
    • Organizer
      25th International Carbohydrate Symposium
    • Year and Date
      2010-08-05
    • Related Report
      2010 Final Research Report
  • [Presentation] Molecular interactions of concanavalin A lectin with phenyl glucoside derivatives using STD NMR spectra2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      25th International Carbohydrate Symposium
    • Place of Presentation
      幕張メッセ
    • Year and Date
      2010-08-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] NMR determination of the glycosidic linkage formed by the transglycosylation by Mucor hiemalis endo-β-N-acetylglucosaminidase2010

    • Author(s)
      T.Yamanoi, Y.Oda, K.Katsuraya, K.Osumi, C.Kurosaki, S.Koshiba, T.Inazu, K.Yamamoto
    • Organizer
      25th International Carbohydrate Symposium
    • Year and Date
      2010-08-04
    • Related Report
      2010 Final Research Report
  • [Presentation] NMR determination of the glycosidic linkage formed_by the transglycosylation by Mucor hiemalis endo-β-N-acetylglucosaminidase2010

    • Author(s)
      山ノ井孝、小田慶喜
    • Organizer
      25th International Carbohydrate Symposium
    • Place of Presentation
      幕張メッセ
    • Year and Date
      2010-08-04
    • Related Report
      2010 Annual Research Report
  • [Presentation] シクロデキストリン類のドキソルビシン包接作用とNMR解析2009

    • Author(s)
      山ノ井孝
    • Organizer
      第2回シクロデキストリンワークショプ
    • Year and Date
      2009-11-01
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] Fischerグリコシド化法によるN-アセチル-α-D-グルコサミニド合成と抗ピロリ菌活性評価2009

    • Author(s)
      山ノ井孝・藤田雅也・中山淳
    • Organizer
      第29回日本糖質学会
    • Year and Date
      2009-09-11
    • Related Report
      2010 Final Research Report
  • [Presentation] STD NMRスペクトルを用いたアルブチン誘導体のコンカナバリンAへの会合特性解析2009

    • Author(s)
      山ノ井孝・鬘谷要・小田慶喜
    • Organizer
      第29回日本糖質学会
    • Year and Date
      2009-09-11
    • Related Report
      2010 Final Research Report
  • [Presentation] Fischer グリコシド化法によるN-アセチル-α-D-グルコサミニド合成と抗ピロリ菌活性評価2009

    • Author(s)
      山ノ井孝、藤田雅也、中山淳
    • Organizer
      第29回日本糖質学会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] STD NMRスペクトルを用いたアルブチン誘導体のコンカナバリンAへの会合特性解析2009

    • Author(s)
      山ノ井孝、鬘谷要、小田慶喜
    • Organizer
      第29回日本糖質学会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] 効率的なD-プシコフラノシド化法に関する研究2009

    • Author(s)
      石山敏明・山ノ井孝・渡邊幹夫
    • Organizer
      第29回日本糖質学会
    • Year and Date
      2009-09-10
    • Related Report
      2010 Final Research Report
  • [Presentation] 効率的なD-プシコフラノシド化法に関する研究2009

    • Author(s)
      石山敏明、山ノ井孝、渡邊幹夫
    • Organizer
      第29回日本糖質学会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] N-アセチルグルコサミン含有物質のH.pyloriへの増殖抑制効果2009

    • Author(s)
      藤田雅也・森昌子・土田明子・山ノ井孝・松田翔・山田一作・水野真盛・閻会敏・星野瞳・中山淳
    • Organizer
      第15回日本ヘリコバクラー学会
    • Year and Date
      2009-06-25
    • Related Report
      2010 Final Research Report
  • [Presentation] N-アセチルグルコサミン含有物質のH.pylori への増殖抑制効果2009

    • Author(s)
      藤田雅也
    • Organizer
      第15回日本ヘリコバクター学会
    • Place of Presentation
      東京ステーションコンファレンス
    • Year and Date
      2009-06-25
    • Related Report
      2009 Annual Research Report
  • [Presentation] L-フルクトース及びD-プシコースを用いたグリコシル化反応の研究2008

    • Author(s)
      石山敏明・山ノ井孝・渡邊幹夫、希少糖
    • Organizer
      日本化学会第2回関東支部大会
    • Year and Date
      2008-09-08
    • Related Report
      2010 Final Research Report
  • [Presentation] 希少糖、L-フルクトース及びD-プシコースを用いたグリコシル化反応の研究2008

    • Author(s)
      石山敏明
    • Organizer
      日本化学会第2回関東支部大会
    • Place of Presentation
      群馬大学桐生キャンパス
    • Year and Date
      2008-09-08
    • Related Report
      2008 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.noguchi.or.jp/annai_kiso.html

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.noguchi.or.jp/annai_kiso.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.noguchi.or.jp/annai_kiso.html

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] フルオラス化糖結合型クラウンエーテル誘導体2010

    • Inventor(s)
      山ノ井孝・吉田彰宏・小田慶喜
    • Industrial Property Rights Holder
      野口研究所
    • Industrial Property Number
      2010-055097
    • Filing Date
      2010-03-11
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] フルオラス化糖結合型クラウンエーテル誘導体2010

    • Inventor(s)
      山ノ井孝, 小田慶喜, 吉田彰宏
    • Industrial Property Rights Holder
      財団法人野口研究所
    • Industrial Property Number
      2010-055097
    • Filing Date
      2010-03-11
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] N-アセチルグルコサミンβ結合単糖誘導体を含有するピロリ菌増殖抑制制御2008

    • Inventor(s)
      中山淳・白井孝・山ノ井孝・藤田雅也・森昌子
    • Industrial Property Rights Holder
      信州大学・野口研究所
    • Industrial Property Number
      2008-263880
    • Filing Date
      2008-10-10
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] N-アセチルグルコサミンβ結合単糖誘導体を含有するピロリ菌増殖抑制制御2008

    • Inventor(s)
      中山淳
    • Industrial Property Rights Holder
      信州大学・野口研究所
    • Industrial Property Number
      2008-263880
    • Filing Date
      2008-10-10
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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