Development of novel sugar-related organic compounds involved in insulin signaling mechanism

• Project/Area Number: 19590015
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Teikyo University
• Principal Investigator: TAKAHASHI Hideyo Teikyo University, 薬学部, 教授 (10266348)
• Co-Investigator(Kenkyū-buntansha): 南目 梨江 帝京大学, 薬学部, 助手 (70349257)
• Project Period (FY): 2007 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2007: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: Coyolosa / エーテル結合糖 / 還元的エーテル化 / 血糖降下作用 / 糖鎖 / オキシラン / IC-メチル糖 / インスリン / coyolosa / カルバメート / 1C-メチル糖 / トレハロース

Research Abstract

本研究は、血糖降下作用を有する希少な糖類及びその関連物質を効率よく化学合成する方法論の確立と、それらを用いたインスリン情報伝達機構の解明を目的としている。血糖降下作用を有する天然物であるCoyolosaの構造を基本とし、還元的エーテル化反応やオキシランの開環反応によって様々なエーテル結合糖を化学合成することに成功した。また、糖-タンパクの認識機構を解明する新しい方法論の開発も行っている。

Research Products

• [Journal Article] Identification of trimannnoside-recognizing peptide sequences from a T7 phage display screen using a QCM device (2009)
  • Author(s): Nishiyama, Kazusa ; Takakusagi, Yoichi ; Kusayanagi, Tomoe ; Matsumoto, Yuki ; Habu, Shiori ; Kuramochi, Kouji ; Sugawara, Fumio ; Sakaguchi, Kengo ; Takahashi, Hideyo ; Natsugari, Hideaki ; Kobayashi, Susumu.
  • Journal Title: Bioorganic & Medicinal Chemistry 17 4 Pages: 195-202
  • Peer Reviewed
• [Journal Article] Identification of trimannoside-recognizing peptide sequences from a T7 phase display screen using a QCM device. (2009)
  • Author(s): Kazusa Nishiyama
  • Journal Title: Bioorganic & Medicinal Chemistry 17 Pages: 195-202
  • Peer Reviewed
• [Journal Article] Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes (2008)
  • Author(s): Nishiyama, Kazusa ; Nakayama, Takahiro ; Natsugari, Hideaki ; Takahashi, Hideyo
  • Journal Title: Synthesis Pages: 3761-3768
  • Peer Reviewed
• [Journal Article] Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement (2008)
  • Author(s): Sawada, Daisuke ; Sasayama, Shinya ; Takahashi, Hideyo ; Ikegami, Shiro.
  • Journal Title: Tetrahedron 644 Pages: 8780-8788
  • Peer Reviewed
• [Journal Article] Synthesis of ether-linked sugar by nucleophilic opening of carbohydrate oxiranes. (2008)
  • Author(s): Kazusa Nishiyama
  • Journal Title: Synthesis Pages: 3761-3768
  • Peer Reviewed
• [Journal Article] Novel Synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement. (2008)
  • Author(s): Daisuke Sawada
  • Journal Title: Tetrahedron 64 Pages: 8780-8788
  • Peer Reviewed
• [Journal Article] Development of ketoside-type analogues of trehalose by using □-stereoselective o-glycosidation of ketose (2007)
  • Author(s): Namme, Rie ; Mitsugi, Takashi ; Takahashi, Hideyo ; Ikegami, Shiro
  • Journal Title: European Journal of Organic Chemistry Pages: 3758-3764
  • Peer Reviewed
• [Journal Article] Characterization of the reaction between sialic acid (N-acetylneuraminic acid) and hydrogen peroxide (2007)
  • Author(s): Iijima, Ryosuke ; Takahashi, Hideyo ; Ikegami, Shiro ; Yamazaki, Masatoshi.
  • Journal Title: Biological & Pharmaceutical Bulletin 30 Pages: 580-582
  • NAID: 110006239207
  • Peer Reviewed
• [Journal Article] Novel synthesis of carbamate-linked oligosaccharides based on modified Curtius rearrangement (2007)
  • Author(s): Sawada, Daisuke ; Sasayama, Shinya ; Takahashi, Hideyo ; Ikegami, Shiro
  • Journal Title: European Journal of Organic Chemistry Pages: 1064-1068
  • Peer Reviewed
• [Journal Article] 新規なエーテル結合糖の合成法の開発及び生物活性物質創製への応用 (2007)
  • Author(s): 高橋秀依
  • Journal Title: 薬学研究の進歩研究成果報告集 23巻 Pages: 17-23
• [Journal Article] Novel Synthesis of carbamate-hnked oligosaccharides based on modified Curtius rearrangement (2007)
  • Author(s): Sawada, Daisuke
  • Journal Title: European Journal of Organic Chemistry Pages: 1064-1068
  • Peer Reviewed
• [Journal Article] Characterizatio of the reaction between sialic acid (N-acetylneuraminic acid) and hydrogen peroxide (2007)
  • Author(s): Iijima, Ryosuke
  • Journal Title: Biological & Pharmaceutical Bulletin 30 Pages: 580-582
  • Peer Reviewed
• [Journal Article] Development of ketoside-type analogues of trehalose by using α-stereose lective O-glycosidation of ketose (2007)
  • Author(s): Namme, Rie
  • Journal Title: European Journa lof Organic Chemistry Pages: 1064-1068
  • Peer Reviewed
• [Presentation] トリマンノース由来の分子プローブの合成とQCM-PD-SAM法を用いた結合ペプチドの同定 (2009)
  • Author(s): 西山和沙、小林進、草柳友恵、松本勇記、高草木洋一、倉持幸司、菅原二三男、坂口謙吾、高橋秀依、夏苅英昭
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] 糖認識機能解明のための分子プローブの合成 (2008)
  • Author(s): 西山 和沙
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2008-11-04
• [Presentation] 糖鎖認識機能解明のための分子プローブの合成 (2008)
  • Author(s): 西山和沙、小林進、草柳友恵、松本勇記、高草木洋一、倉持幸司、菅原二三男、坂口謙吾、高橋秀依、夏苅英昭
  • Organizer: 第34回反応と合成の進歩シンポジウム
  • Place of Presentation: 京都
• [Presentation] トリマンノース由来の分子プローブの合成とQCM-PD法による結合ペプチドの探索 (2008)
  • Author(s): 西山和沙、草柳友恵、高草木洋一、倉持幸司、菅原二三男、坂口謙吾、高橋秀依、夏苅英昭、小林進
  • Organizer: 日本薬学会第128年会
  • Place of Presentation: 横浜
• [Presentation] 簡単な化学ができること (2007)
  • Author(s): 高橋秀依
  • Organizer: 相模中央化学研究所開所記念講演会
  • Place of Presentation: 綾瀬
  • Year and Date: 2007-10-30
• [Presentation] 簡単な化学ができること (2007)
  • Author(s): 高橋 秀依
  • Organizer: 相模中央化学研究所開所記念講演会
  • Place of Presentation: 相模中央化学研究所
  • Year and Date: 2007-10-30