Structural Analysis and Elucidation of the Molecular Basis of Lipid Raft

• Project/Area Number: 18710186
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Living organism molecular science
• Research Institution: Tohoku University (2008); Kwansei Gakuin University (2007); Osaka University (2006)
• Principal Investigator: KASAI Yusuke Tohoku University, 大学院・理学研究科, COE フェロー (50379286)
• Project Period (FY): 2006 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥3,830,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥330,000); Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2007: ¥1,100,000 (Direct Cost: ¥1,100,000); Fiscal Year 2006: ¥1,300,000 (Direct Cost: ¥1,300,000)
• Keywords: 生体膜 / 分子複合体 / 固体NMR / アンフォテリシンB / エラジタンニン / 反転糖 / 配座制御 / グリコシルエステル / 天然物合成 / 有機合成 / 構造解析 / 2,4-架橋グルコース / ステロール / 共有結合連結 / 円二色性

Research Abstract

脂質ラフトは生体膜上に形成されるドメインであり、様々なシグナル伝達の場として機能していると推測されている。本研究では、脂質ラフトの分子基盤解明のための分析手法として、固体NMRが有用であることを示すことができた。また、植物由来の抗酸化活性を有する天然物エラジタンニンの合成を通して、新たなピラノース配座制御法の確立、天然物の高効率的合成方法および高立体選択的グリコシルエステル調製法を開発した。

Research Products

• [Journal Article] A 2,4-O-[(Z)-2-Butenylene]-Bridged Glucopyranose : Efficient Construction of the Bicyclic Skeleton and its Axial-rich Twist-Boat Conformation (2009)
  • Author(s): Cao Yang, Yusuke Kasai, Masafumi Bando, Mayumi Kawagoe, Hidetoshi Yamada
  • Journal Title: Tetrahedron 65(12) Pages: 2574-2578
  • Peer Reviewed
• [Journal Article] A 2, 4-O-[(Z)-2-Butenylene]-Bridged Glucopyranose: Efficient Construction of the Bicyclic Skeleton and its Axial-rich Twist-Boat Conformation (2009)
  • Author(s): Cao Yang
  • Journal Title: Tetrahedron 12 Pages: 2574-2578
  • Peer Reviewed
• [Journal Article] Total Synthesis of (-)-Corilagin (2008)
  • Author(s): Hidetoshi Yamada, Kohei Nagao, Kazutoyo Dokei, Yusuke Kasai, Naoki Michihata
  • Journal Title: J. Am. Chem. Soc. 130(24) Pages: 7566-7567
• [Journal Article] Orientation of Fluorinated Cholesterol in Lipid Bilayers Analyzed by ^<19>F Tensor Calculation and Solid State NMR (2008)
  • Author(s): Nobuaki Matsumori, Yusuke Kasai, Tohru Oishi, Michio Murata, Kaoru Nomura
  • Journal Title: J. Am. Chem. Soc. 130(14) Pages: 4757-4766
  • Peer Reviewed
• [Journal Article] Self-Assembled Amphotericin B Is Probably Surrounded by Ergosterol : Bimolecular Interactions as Evidenced by Solid-State NMR and CD Spectra (2008)
  • Author(s): Yusuke Kasai, Nobuaki Matsumori, Yuichi Umegawa, Shigeru Matsuoka, Hiroyuki Ueno, Hiroki Ikeuchi, Tohru Oishi, Michio Murata
  • Journal Title: Chem. Eur. J. 14(4) Pages: 1178-1185
  • Peer Reviewed
• [Journal Article] Synthesis of Enantiopure 2-Aryl-2-methoxypropionic Acids and Determination of Their Absolute Configurations by X-ray Crystallography (2008)
  • Author(s): Satoshi Sekiguchi, Junpei Naito, Hiromi Taji, Yusuke Kasai, Akinori Sugio, Shunsuke Kuwahara, Masataka Watanabe, Nobuyuki Harada
  • Journal Title: Chirality 20(3/4) Pages: 251-264
  • Peer Reviewed
• [Journal Article] Total Synthesis of (-)-Corilagin (2008)
  • Author(s): Hidetoshi Yamada
  • Journal Title: Journal of the American Chemical Society 24 Pages: 7566-7567
  • Peer Reviewed
• [Journal Article] Orientation of Fluorinated Cholesterol in Lipid Bilayers Analyzed by ^<19>F Tensor Calculation and Solid State NMR (2008)
  • Author(s): Nobuaki Matsumori
  • Journal Title: Journal of the American Chemical Society 14 Pages: 4757-4766
  • Peer Reviewed
• [Journal Article] Self-Assembled Amphotericin B Is Probably Surrounded by Ergosterol: Bimolecular Interactions as Evidenced by Solid-State NMR and CD Spectra (2008)
  • Author(s): Kasai, Y.
  • Journal Title: Chemistry, a European Journal 14 Pages: 1178-1185
  • Peer Reviewed
• [Journal Article] Synthesis of Enantiopure 2-Aryl-2-methoxypropionic Acids and Determination of Their Absolute Configurations by X-ray Crystallography (2008)
  • Author(s): Sekiguchi, S.
  • Journal Title: Chirality 20 Pages: 251-264
  • Peer Reviewed
• [Journal Article] Conformational Analysis of MαNP esters, Powerful Chiral Resolution and ^1H NMR Anisotropy Tools. Aromatic Geometry and Solvent Effects on Δδ Values (2007)
  • Author(s): Yusuke Kasai, Akinori Sugio, Satoshi Sekiguchi, Shunsuke Kuwahara, Takatoshi Matsumoto, Masataka Watanabe, Akio Ichikawa, Nobuyuki Harada
  • Journal Title: Eur. J. Org. Chem. (11) Pages: 1811-1826
  • Peer Reviewed
• [Journal Article] Crystalline State Conformational Analysis of MαNP esters, Powerful Resolution and Chiral ^1H NMR Anisotropy Tools (2007)
  • Author(s): Shunsuke Kuwahara, Junpei Naito, Yoko Yamamoto, Yusuke Kasai, Takuma Fujita, Kazutoshi Noro, Kumiko Shimanuki, Megumi Akagi, Miwa Watanabe, Takatoshi Matsumoto, Masataka Watanabe, Akio Ichikawa, Nobuyuki Harada
  • Journal Title: Eur. J. Org. Chem. (11) Pages: 1827-1840
  • Peer Reviewed
• [Journal Article] Conformational analysis of methyl 2-methyl-2-(1-naphthyl)propionate (2007)
  • Author(s): Takatoshi Matsumoto, Yoshio Kinoshita, Yusuke Kasai, Shunsuke Kuwahara, Masataka Watanabe
  • Journal Title: Tetrahedron 63(3) Pages: 615-624
  • Peer Reviewed
• [Journal Article] Conformational analysis of methyl 2-methoxy-2-(1-naphthyl) propionate (2007)
  • Author(s): Matsumoto, T.
  • Journal Title: Tetrahedron 63 Pages: 615-615
• [Journal Article] Conformationa Analysis of MαNP esters, Powerful Chiral Resolution and ^1H NMR Anisotropy Tools. Aromatic Geometry and Solvent Effects on Δδ Values
  • Author(s): Kasai, Y.
  • Journal Title: European Journal of Organic Chemistry (In press)
• [Journal Article] Crystalline State Conformational Analysis of MαNP esters, Powerful Resolution and Chiral ^1H NMR Anisotropy Tools
  • Author(s): Kuwahara, S.
  • Journal Title: European Journal of Organic Chemistry (In press)
• [Presentation] (+)-ダビジインの全合成の改善 (2009)
  • Author(s): 葛西祐介, 道畑直起, 西村英久, 山田英俊
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 千葉
  • Year and Date: 2009-03-27
• [Presentation] 新規リフォールディング剤の効果の検討 (2008)
  • Author(s): 垰幸作, 伊藤廉, 葛西祐介, 山田英俊, 芝野智久, 白木賢太郎, 日高雄二, 奥村正樹, 大須賀陽子, 山口宏
  • Organizer: 第45回ペプチド討論会
  • Place of Presentation: 東京
  • Year and Date: 2008-10-29
• [Presentation] ダビジイン全合成を目的としたβ-Glucosyl Gallateの効率的合成法 (2008)
  • Author(s): 河内祐樹, 葛西祐介, 西村英久, 山田英俊
  • Organizer: 第28回日本糖質学会年会
  • Place of Presentation: 筑波
  • Year and Date: 2008-08-18
• [Presentation] Hipporhamninの合成研究 (2008)
  • Author(s): 葛西祐介, 山田英俊
  • Organizer: 第35回有機反応懇談会
  • Place of Presentation: 大阪
  • Year and Date: 2008-08-01
• [Presentation] 1,3-ヘキサヒドロキシジフェノイル基を有するエラジタンニン類の合成研究 (2008)
  • Author(s): 葛西 祐介
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学
  • Year and Date: 2008-03-30
• [Presentation] 1,3-ヘキサヒドロキシジフェノイル基を有するエラジタンニン類の合成研究 (2008)
  • Author(s): 葛西祐介, 山田英俊
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-26
• [Presentation] 4,6-ヘキサヒドロキシジフェノイル架橋エラジタンニン、Strictininの合成研究 (2008)
  • Author(s): 道畑直起, 谷川康太郎, 葛西祐介, 山田英俊
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-26
• [Presentation] 1,2,4-エチリジングルコースを用いた3,6-HHDP架橋グルコースの高効率合成 (2008)
  • Author(s): 谷川康太郎, 葛西祐介, 山田英俊
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-26
• [Presentation] 酒石酸誘導体を不斉補助基としたhexahydroxydiphenoyl基の不斉合成 (2008)
  • Author(s): 藤本翔平, 葛西祐介, 今川洋, 岡田康則, 山田英俊
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-26
• [Presentation] アンフォテリシンB-ステロール連結体が脂質膜中で形成する分子複合体の構造解析 (2007)
  • Author(s): 葛西祐介, 梅川雄一, 松森信明, 大石徹, 村田道雄
  • Organizer: 日本化学会第87春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2007-03-25
• [Presentation] Membrane Permeabilizing Assembly of Amphotericin B - REDOR Experiments for Fluorine-labeled Antibiotics and Sterols (2006)
  • Author(s): Yusuke Kasai, Nobuaki Matsumori, Hiroshi Tsuchikawa, Yuichi Umegawa, Tohru Oishi, Michio Murata
  • Organizer: 第45回NMR討論会
  • Place of Presentation: 京都
  • Year and Date: 2006-11-22
• [Presentation] Amphotericin B-Sterol Covalent Conjugates Forming Molecular Assemblage in Membrane Studied by Solid State NMR (2006)
  • Author(s): Yusuke Kasai, Nobuaki Matsumori, Shigeru Matsuoka, Yuichi Umegawa, Hiroyuki Ueno, Hiroki Ikeuchi, Tohru Oishi, Michio Murata
  • Organizer: ICOB-5 & ISCNP-25 IUPAC International Conference on Biodiversity and Natural Products
  • Place of Presentation: Kyoto, Japan
  • Year and Date: 2006-07-23
• [Presentation] アンフォテリシンB-ステロール連結体が形成する複合体の固体NMRによる構造解析 (2006)
  • Author(s): 葛西祐介
  • Organizer: 第41回天然物化学談話会
  • Place of Presentation: 北海道
  • Year and Date: 2006-07-03
• [Patent(Industrial Property Rights)] リフォールディング剤および蛋白質のリフォールディング方法 (2008)
  • Inventor(s): 山口宏, 伊藤廉, 葛西祐介, 山田英俊
  • Industrial Property Rights Holder: 山口宏, 伊藤廉, 葛西祐介, 山田英俊
  • Filing Date: 2008-10-28
• [Patent(Industrial Property Rights)] 特許 (2008)
  • Inventor(s): 山口宏
  • Industrial Property Rights Holder: 学校法人関西学院
  • Industrial Property Number: 2008-277109
  • Filing Date: 2008-10-28