Development of Exhaustive Synthesis of Glycopeptides by using Multiphase Organic Reaction System

2008 Fiscal Year Final Research Report

• Project/Area Number: 18380071
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Tokyo University of Agriculture and Technology
• Principal Investigator: CHIBA Kazuhiro Tokyo University of Agriculture and Technology, 大学院・連合農学研究科, 教授 (20227325)
• Project Period (FY): 2006 – 2008
• Keywords: 糖鎖 / 有機化学 / 化学合成 / 生体分子 / 生理活性

Research Abstract

本研究では、近年見出したシクロアルカン系有機溶媒相溶二相化現象を応用し、多様なオリゴ糖-ペプチド複合体標品のワンポット逐次多段階化学合成法を確立する新たな方法について研究を実施し、目的とする糖ペプチド合成システムを構築した。また、このシステムを応用し、オリゴ糖、糖ペプチドなど十数段階から数十段階を要する物質の簡易操作による合成に成功した。

Research Products

• [Journal Article] Anodic Carbon Carbon Bond Formation in Lithium Perchlorate/Nitromethane Electrolyte Solution (2009)
  • Author(s): Kazuhiro Chiba, Shokaku Kim
  • Journal Title: Electrochemistry Vol.77, No.1 Pages: 21-29
  • Peer Reviewed
• [Journal Article] Electrocatalytic Formal[2+2]Cycloaddition Reactions between Anodically Activated Aliphatic Enol Ethers and Unactivated Olefins Possessing an Alkoxyphenyl Group (2009)
  • Author(s): Yohei Okada, Ryoichi Akaba, Kazuhiro Chiba
  • Journal Title: Org. Lett. 11(4) Pages: 1033-1035
  • Peer Reviewed
• [Journal Article] Construction of Cold triggered/Heat destroyed Emulsions for Use as a Practical Cold Storage Thermal History Indicator (2009)
  • Author(s): Tatsuya Mizoguch, Kohdai Nagata, Makoto Kitsunai, Kumi Hirose, Akira Hirasawa, Kazuhiro Chiba
  • Journal Title: J.Sci.Food Agric. (in press)
  • Peer Reviewed
• [Journal Article] Cold-triggered/Heat destroyed Emulsions Composed of Phospholipids and Triacylglycerols as Thermal History Indicators for Cold Chain Distribution Systems (2008)
  • Author(s): Kohdai Nagata, Tatsuya Mizoguchi, Makoto Kitsunai, Kumi Hirose, Akira Hirasawa, Kazuhiro Chiba
  • Journal Title: J. Sci. Food Agric. 88 Pages: 1019-1024
  • Peer Reviewed
• [Journal Article] A cycloalkane based thermomorphic system for palladium catalyzed cross coupling reactions (2008)
  • Author(s): Shokaku Kim, Keisuke Yamamoto, Kanako Hayashi, Kazuhiro Chiba
  • Journal Title: Tetrahedron 64(12) Pages: 2855-2863
  • Peer Reviewed
• [Journal Article] Solution Phase Oligosaccharide Synthesis in a Cycloalkane Based Thermomorphic System (2008)
  • Author(s): Shokaku Kim, Ai Tsuruyama, Akihiro Ohmori, Kazuhiro Chiba
  • Journal Title: Chem.Comm. Pages: 1816-1818
  • Peer Reviewed
• [Journal Article] An Oxidative Carbon-Carbon Bond Formation System in Cycloalkane Based Thermomorphic Multi Phase Solution (2008)
  • Author(s): Shokaku Kim, Satoko Noda, Kanako Hayashi, Kazuhiro Chiba
  • Journal Title: Org. Lett. 10(9) Pages: 1827-1829
  • Peer Reviewed
• [Journal Article] Phase separable Aqueous Amide Solutions as a Thermal History Indicator (2008)
  • Author(s): Makoto KITSUNAI, Kentaro MIYAJIMA, Yuzuru MIKAMI, Shokaku KIM, Akira HIRASAWA, Kazuhiro CHIBA
  • Journal Title: Biosci. Biotech.Biochem Vol.76, No.12 Pages: 871-873
  • Peer Reviewed
• [Journal Article] Construction of Cycloalkane based Thermomorphic(CBT)Electrolyte Solution Systems and Application for Anodic Conversion of a Furan Derivative (2008)
  • Author(s): Tomio NAGANO, Yuzuru MIKAMI, Shokaku KIM, Kazuhiro CHIBA
  • Journal Title: Electrochemistry Vol.76, No.12 Pages: 874-879
  • Peer Reviewed
• [Journal Article] Cyclic Voltammetric Studies on Anodic Cycloaddition Reactions between Electrogenerated Phenoxonium Cations and Alkenes (2008)
  • Author(s): Kumi HIROSE, Shokaku KIM, Kazuhiro CHIBA
  • Journal Title: Electrochemistry Vol.76, No.12 Pages: 871-873
  • Peer Reviewed
• [Journal Article] Laser Raman Detection of an Electrogenerated Intermediate during Anodic Synthesis of Dihydrobenzofurans via Formal [3+2] Cycloaddition (2007)
  • Author(s): Tomohiro Marui, Shinya Kajita, Yoshihiro Katayama, Kazuhiro Chiba
  • Journal Title: Electrochem. Commun. 9 Pages: 1331-1336
  • Peer Reviewed
• [Journal Article] シクロアルカン可溶化疎水性タグを用いた化学プロセスの効率化,"化学工業" (2007)
  • Author(s): 千葉一裕
  • Journal Title: (特集)コンビナトリアルケミストリーの新展開 VOL.58, No.4 Pages: 281-287
  • Peer Reviewed
• [Journal Article] Electrocatalytic Formal [2+2] Cycloaddition Reactions between Anodically Activated Enyloxy Benzene and Alkenes (2007)
  • Author(s): Arata, M. ; Miura, T. ; Chiba, K
  • Journal Title: Org. Lett. 9(21) Pages: 4347-4350
  • Peer Reviewed
• [Journal Article] Rate Enhancement of Diels Alder Reactions in Aqueious Perfluorinated Emulsions (2006)
  • Author(s): Kohsuke Nishimoto, Shokaku Kim, Yoshikazu Kitano, Masahiro Tada, Kazuhiro Chiba
  • Journal Title: Org. Lett. 8(24) Pages: 5545-5547
  • Peer Reviewed
• [Journal Article] A convenient method for the preparation of benzyl isocyanides (2006)
  • Author(s): Kitano, Yoshikazu ; Manoda, Tetsuya ; Miura, Teppei ; Chiba, Kazuhiro ; Tada, Masahiro
  • Journal Title: Synthesis (3) Pages: 405-410
  • Peer Reviewed
• [Journal Article] Microwave promoted Suzuki Miyaura coupling reactions in a ycloalkane based thermomorphic biphasic system (2006)
  • Author(s): Hayashi, Kanako ; Kim, Shokaku ; Kono, Yusuke ; Tamura, Mihoko ; Chiba, Kazuhiro
  • Journal Title: Tetrahedron Letters 47(2) Pages: 171-174
  • Peer Reviewed
• [Journal Article] Electrochemical Enol Ether Olefin Cross Metathesis in a Lithium Perchlorate Nitromethane Electrolyte Solution (2006)
  • Author(s): Teppei Miura, Shokaku Kim, Yoshikazu Kitano, Masahiro Tada, Kazuhiro Chiba
  • Journal Title: Angew. Chem. Int. Ed. 45(9) Pages: 1461-1463
  • Peer Reviewed
• [Journal Article] Cycloalkane based Thermomorphic Electrochemical Reaction System Composed of Nitrile solvents (2006)
  • Author(s): Fumiyoshi Tanaka, Michiko Arata, Kanako Hayashi, Shokaku Kim and Kazuhiro Chiba
  • Journal Title: Electrochemistry 74(8) Pages: 625-627
  • Peer Reviewed
• [Journal Article] Reversible capture of electrogenerated intermediates by liquefiable micro particles containing an amphiphilic tag (2006)
  • Author(s): Kanako Hayashi, Shokaku Kim, and Kazuhiro Chiba
  • Journal Title: Electrochemistry 74(8) Pages: 621-624
  • Peer Reviewed
• [Presentation] (2009)
  • Author(s): 岡田洋平・赤羽良一・千葉一裕
  • Organizer: 日本化学会春季年会
  • Year and Date: 20090000
• [Presentation] (2009)
  • Author(s): 岡田洋平・赤羽良一・千葉一裕
  • Organizer: 電気化学会大会
  • Year and Date: 20090000
• [Presentation] (2008)
  • Author(s): 岡田洋平、赤羽良一、千葉一裕
  • Organizer: 第32回有機電子移動討論会
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): 吉岡朋彦・金承鶴・千葉一裕
  • Organizer: 第32回有機電子移動討論会
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): 大岡直哉・千葉一裕
  • Organizer: 第32回有機電子移動討論会
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): 河合朋充・杉原万理・千葉一裕
  • Organizer: 第32回有機電子移動討論会
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): Yohei Okada, Ryoichi Akaba, Kazuhiro Chiba
  • Organizer: 213^<th> Electrochemical Society Meeting
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): Tomohiko Yoshioka, Shokaku Kim, Kazuhiro Chiba
  • Organizer: 213^<th> Electrochem.Soc. Meeting
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): K.Nishimoto, S.Kim, K.Chiba
  • Organizer: 213^<th> Electrochem. Soc. Meeting
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): Kumi Hirose, Kohsuke Nishimoto, Shokaku Kim, Kazuhiro Chiba
  • Organizer: 213^<th> Electrochem.Soc. Meeting
  • Year and Date: 20080000
• [Presentation] (2008)
  • Author(s): 千葉一裕
  • Organizer: 第27回Combinatorial Chemistry研究会
  • Year and Date: 20080000
• [Presentation]
  • Author(s): 尾関歩未、吉岡朋彦、金承鶴、千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 植松潤平、廣瀬久美、千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 西村宗親、飯島志行、金承鶴、千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 小池幹男・千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 有吉佐奈恵・千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 中山英、岡田洋平、三上由鶴、金承鶴、千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): ゲゲンタナ・藤田・千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 大岡直哉, 西本浩介, 千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Presentation]
  • Author(s): 河合朋充・山本圭介・千葉一裕
  • Organizer: 日本農芸化学会2009年度大会
• [Book] 食品流通の安全を監視する温度履歴センサーシール (2008)
  • Author(s): 千葉一裕
  • Total Pages: 10-17
  • Publisher: 食品と技術
• [Book] アフィニティー解析法、"分子間相互作用解析ハンドブック-タンパク質とタンパク質・核酸・糖・低分子間のネットワーク解析"(磯辺俊明、中山敬一、伊藤隆司(編集)) (2007)
  • Author(s): 高橋信弘、藤山沙理、千葉一裕
  • Total Pages: 45-52
  • Publisher: 羊土社
• [Book] Development of Solution Phase Peptide Synthesis Protocol toward Automatic Synthesizer by Using Precipitation Method, Peptide Science(S.Aimoto, S. Ono (Eds.)) (2007)
  • Author(s): A. Tsuruyama, K. Abe, T. Higashiguchi, T Yoshioka, K. Chiba
  • Total Pages: 43-44
  • Publisher: The Japanese Peptide Society
• [Book] Development of an Automatic Solution Phase Peptide Synthesizer, Peptide Science(S.Aimoto, S. Ono (Eds.)) (2007)
  • Author(s): K. Abe, A. Tsuruyama, T. Higashiguchi, K. Chiba
  • Total Pages: 183-184
  • Publisher: The Japanese Peptide Society
• [Book] One Pod Solution Phase Peptide Synthesis Using Less Polar Platforms, Peptide Science(S.Aimoto S. Ono(Eds.)) (2007)
  • Author(s): T. Yoshioka, S. Yamamoto, M. Shimizu, S. Kim, K. Chiba
  • Total Pages: 193-194
  • Publisher: The Japanese Peptide Society
• [Book] Synthesis of Various Proline Derivatives Using Organic Electrochemical Methods, Peptide Science(S. Aimoto, S. Ono (Eds.)) (2007)
  • Author(s): K. Yamamoto, M. Sugihara, S. Kim, K. Chiba
  • Total Pages: 195-196
  • Publisher: The Japanese Peptide Society