Construction and functionalization of molecular containers composed of peptidemimetic chiral bowls having C3-symmetry

• Project/Area Number: 21550129
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Functional materials chemistry
• Research Institution: Chiba University
• Principal Investigator: AKAZOME Motohiro 千葉大学, 大学院・工学研究科, 准教授 (10261934)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 超分子化学 / ホスト-ゲスト化学 / ボウル型化合物

Research Abstract

We synthesized bowl-shaped cyclic peptidomimetic s from amino acids and elucidated their conformation. These cyclic peptides as new host compounds were examined their guest binding ability. After introduction of aggregable functional group on the rim of the bowl-shaped cyclic peptide, the aggregation of the bowls was observed by NMR spectra with varying concentration of the bowl.

Research Products

• [Journal Article] Synthesis andC2-Symmetric Structure of a Cyclotetrapeptide Composed of Anthranilic Acidand Leucine (2011)
  • Author(s): Motohiro Akazome, Masashi Enzu, Koji Takagi, Shoji Matsumoto
  • Journal Title: Chirality Volume: 23 Pages: 568-573
  • Peer Reviewed
• [Journal Article] Inclusion of aliphatic alcohols in pockets of (S)-threonyl-(S)-phenylglycine using grinding (2011)
  • Author(s): Motohiro Akazome, Shusaku Toma, Tatsunori Horiguchi, Ken Megumi, Shoji Matsumoto
  • Journal Title: method Volume: 67 Pages: 2844-2848
  • Peer Reviewed
• [Journal Article] Synthesis of a Chiral C_3 -Symmetric Bowl-Shaped Cyclohexapeptide Composed of Anthranilic Acid and Leucine (2011)
  • Author(s): Motohiro Akazome, Masashi Enzu, Yohei Goto, Shoji Matsumoto
  • Journal Title: Heterocycles Volume: 82 Pages: 1645-1656
  • Peer Reviewed
• [Journal Article] Synthesis and C_2-Symmetric Structure of a Cyclotetrapeptide Composed of Anthranilic Acid and Leucine (2011)
  • Author(s): Motohiro Akazome
  • Journal Title: Chirality Volume: 23 Issue: 7 Pages: 568-573
  • DOI: 10.1002/chir.20972
  • Peer Reviewed
• [Journal Article] Synthesis of a Chiral C <3>-Symmetric Bowl-Shaped Cyclohexapeptide Composed of Anthranilic Acid and Leucine (2011)
  • Author(s): Motohiro Akazome
  • Journal Title: Heterocycles Volume: 82 Pages: 1645-1656
  • NAID: 40018702744
  • Peer Reviewed
• [Journal Article] Inclusion of aliphatic aloohols in pockets of(S)-threonyl-(S)-phenylglycine using grinding method (2011)
  • Author(s): Motohiro Akazome
  • Journal Title: Tetrahedron Volume: 67 Pages: 2844-2848
  • Peer Reviewed
• [Journal Article] Predominant (S)-Enantioselective Inclusion of Aryl Methyl Sulfoxides by(S)-Isoleucyl-(S)-phenylglycines (2010)
  • Author(s): Motohiro Akazome, Ai Doba, Shoji Matsumoto, Katsuyuki Ogura
  • Journal Title: TheJournal of Organic Chemistry Volume: 65 Pages: 660-665
  • Peer Reviewed
• [Journal Article] Predominant(S)-Enantioselective Inclusion of Aryl Methyl Sulfoxides by(S)-Isoleucyl-(S)-phenylglycines" (2010)
  • Author(s): Motohiro Akazome
  • Journal Title: The Journal of Organic Chemistry Vol.65 Pages: 660-665
  • Peer Reviewed
• [Journal Article] A cyclictrimer of 2-(2-aminophenoxy) propionic acid with a bowl-shaped structure (2009)
  • Author(s): Motohiro Akazome, Junpei Sukegawa, Yohei Goto, Shoji Matsumoto
  • Journal Title: Tetrahedron Letters Volume: 50 Pages: 5382-5385
  • Peer Reviewed
• [Journal Article] A cyclic trimer of 2-(2-aminophenoxy)propionic acid with abowl-shaped structure (2009)
  • Author(s): Motohiro Akazome
  • Journal Title: Tetrahedron Letters Vol.50 Pages: 5382-5385
  • Peer Reviewed
• [Presentation] Cyclic Tripeptides of 2-(Aminophenoxy) alkanoic Acids (2011)
  • Author(s): Motohiro Akazome
  • Organizer: the Bowl-shaped Structure and Molecular Recognition
  • Place of Presentation: Bangkok, (Thailand)
  • Year and Date: 2011-09-08
• [Presentation] Cyclic Tripeptides of 2-(Aminophenoxy)alkanoic Acids : the Bowl-shaped Structure and Molecular Recognition (2011)
  • Author(s): Motohiro Akazome
  • Organizer: The 14th Asian Chemical Congress
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 2011-09-08
• [Presentation] Binding of Quaternary Ammonium Compounds to Bowl-shaped Tripeptides of2-(3-Aminophenoxy) alkanoic acids (2011)
  • Author(s): Motohiro Akazome, Norihiro Hamada, Koji Takagi, Shoji Matsumoto
  • Organizer: 23rdInternational Symposium on Chiral Discrimination (Chirality 2011)
  • Place of Presentation: University of Liverpool (UK)
  • Year and Date: 2011-07-11
• [Presentation] Binding of Quaternary Ammonium Compounds to Bowl-shaped Tripeptides of 2-(3-Aminophenoxy)alkanoic acids (2011)
  • Author(s): Motohiro Akazome
  • Organizer: 23rd International Symposium on Chiral Discrimination
  • Place of Presentation: Liverpool, UK
  • Year and Date: 2011-07-11
• [Presentation] ジペプチドやアミノ酸塩の有機結晶を用いる包接現象と不斉認識 (2010)
  • Author(s): 赤染元浩
  • Organizer: 日本化学会第4回関東支部大会
  • Year and Date: 2010-08-30
• [Presentation] Chiral Bowl-Shaped Structure of Cyclic Peptides Composed of Anthranilic Acid and Leucine (2010)
  • Author(s): Motohiro Akazome, Masashi Enzu, Yohei Goto, Shoji Matsumoto
  • Organizer: 22ndInternational Symposium on Chirality
  • Place of Presentation: 札幌コンベンションセンター(北海道)
  • Year and Date: 2010-07-14
• [Presentation] Chiral Bowl-Shaped Structure of Cyclic Peptides Composed of Anthranilic Acid and Leucine (2010)
  • Author(s): Motohiro Akazome
  • Organizer: 22nd International Symposium on Chirality
  • Place of Presentation: 札幌コンベンションセンター(北海道)
  • Year and Date: 2010-07-14
• [Presentation] アントラニル酸とロイシンからなる環状ペプチドの合成と構造 (2010)
  • Author(s): 赤染元浩, 遠津正, 松本祥治
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学(東大阪市)
  • Year and Date: 2010-03-27
• [Presentation] 2-(2-アミノフェノキシ)アルカン酸からなるオリゴペプチドのヘリックスならびにボウル構造 (2009)
  • Author(s): 赤染元浩, 後藤洋平, 助川順平, 松本祥治
  • Organizer: 第5回ホスト-ゲスト化学シンポジウム
  • Place of Presentation: 宇都宮大学(宇都宮市)
  • Year and Date: 2009-05-30