Synthesis of α-Amino Squaric Acid Incorporated Peptides and Their Biological Activities

• Project/Area Number: 21310145
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Osaka City University
• Principal Investigator: SHINADA Tetsuro 大阪市立大学, 大学院・理学研究科, 教授 (30271513)
• Project Period (FY): 2009 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000); Fiscal Year 2012: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000); Fiscal Year 2011: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000); Fiscal Year 2010: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000); Fiscal Year 2009: ¥6,760,000 (Direct Cost: ¥5,200,000、Indirect Cost: ¥1,560,000)
• Keywords: ペプチド / スクアリン酸 / 固相合成 / ペプチドアナログ / アミノ酸 / 繰り返し連結

Research Abstract

Peptides are one of the pivotal biological materials that plays an important role in biological function. Due to their crucial roles, development of peptide analogs as a tool for investigation of peptide function has attracted much attention from the rese

Research Products

• [Journal Article] Stereoselective Synthesis of E-α,β-Dehydroamino Acid Esters (2013)
  • Author(s): Y. Yasuno, M. Hamada, T. Yamada, T. Shinada,Y. Ohfune
  • Journal Title: Eur. J. Org. Chem. Pages: 1884-1888
  • Peer Reviewed
• [Journal Article] Efficient Total Synthesis of Manzacidin B (2012)
  • Author(s): K.Oe
  • Journal Title: Tetrahedron Lett. Volume: 53 Issue: 26 Pages: 3250-3253
  • DOI: 10.1016/j.tetlet.2012.04.042
  • Peer Reviewed
• [Journal Article] Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multi-Substituted Heterocyclic Compounds (2012)
  • Author(s): T. Okada
  • Journal Title: Org. Lett. Volume: 14 Issue: 24 Pages: 6130-6133
  • DOI: 10.1021/ol302669q
  • Peer Reviewed
• [Journal Article] Total Synthesis of Manzacidins. An Overview and Perspective (2012)
  • Author(s): Y. Ohfune
  • Journal Title: Heterocycles Volume: 85 Issue: 11 Pages: 2617-2649
  • DOI: 10.3987/contents-12-85-11
  • Peer Reviewed
• [Journal Article] Total synthesis of (-)-funebrine via Au-catalyzed regio- and stereoselective γ-butyrolactonization of allenylsilane (2011)
  • Author(s): T.Okada, K.Sakaguchi, T.Shinada, Y.Ohfune
  • Journal Title: Tetrahedron Lett. Volume: 52 Issue: 44 Pages: 5744-5746
  • DOI: 10.1016/j.tetlet.2011.08.050
  • Peer Reviewed
• [Journal Article] Au-catalyzed cyclization of allenylsilanes. Regioselective conversion to 2-amino-4-silylmethylene-γ-butyrolactone (2011)
  • Author(s): T.Okada, K.Sakaguchi, T.Shinada, Y.Ohfune
  • Journal Title: Tetrahedron Lett. Volume: 52 Issue: 44 Pages: 5740-5743
  • DOI: 10.1016/j.tetlet.2011.07.144
  • Peer Reviewed
• [Journal Article] 天然神経毒アミノ酸類の全合成 (2011)
  • Author(s): 大船泰史、品田哲郎
  • Journal Title: 化学工業 Volume: 62 Pages: 642-648
• [Journal Article] Mild and Catalytic Transesterification Reaction using K_2HPO_4 for the Synthesis of Methyl Esters (2010)
  • Author(s): T. Shinada, M. Hamada, K. Miyoshi, M. Higashino, T. Umezawa, Y. Ohfune
  • Journal Title: Synlett Pages: 2141-2145
  • Peer Reviewed
• [Journal Article] Mild and Catalytic Transesterification Reaction using K_2HPO_4 for the Synthesis of Methyl Esters (2010)
  • Author(s): Shinada, T.
  • Journal Title: Synlett Volume: 42 Pages: 2141-2145
  • Peer Reviewed
• [Journal Article] Thiol addition to t-butyl methyl squarate. efficient synthesis of novel sulfur-linked squaryl group-containing glutamate analogs. (2009)
  • Author(s): T. Shinada, A. Yamasaki, Y. Kiniwa, K. Shimamoto, Y. Ohfune
  • Journal Title: Tetrahedron Lett Pages: 4354-4357
  • Peer Reviewed
• [Journal Article] Asymmetric Synthesis of α,α-disubstituted α-amino acids: Strecker and Claisen Approaches. (2009)
  • Author(s): Y. Ohfune, K. Sakaguchi, T. Shinada
  • Journal Title: ACS Symposium Series Volume: 1009 Pages: 57-71
  • Peer Reviewed
• [Journal Article] Thiol Addition to t-Butyl Methyl Squarate. Efficient Synthesis of Novel Sulfur-linked Squaryl Group Containing Glutamate Analogs. (2009)
  • Author(s): T.Shinada, A.Yamazaki, Y.Kiniwa, K.Shimamoto, Y.Ohfune
  • Journal Title: Tetrahedron Letters 50 Pages: 4354-4357
  • Peer Reviewed
• [Presentation] 固相合成による α-アミノスクアリン酸含有ペプチドの合成 (2013)
  • Author(s): 前田健太郎、品田哲郎、大船泰史
  • Organizer: 日本化学会第93 春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
• [Presentation] α-アミノスクアリン酸含有ペプチドの合成 (2013)
  • Author(s): 前田健太郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
• [Presentation] 非天然型アミノ酸構造を有する天然有機化合物の全合成研究 (2012)
  • Author(s): 品田哲郎
  • Organizer: 第39回有機反応懇談会
  • Place of Presentation: 関西大学千里山キャンパス
  • Year and Date: 2012-08-03
• [Presentation] 繰り返し連結によるα-アミノスクアリン酸ペプチドの合成 (2012)
  • Author(s): 前田健太郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応大学
  • Year and Date: 2012-03-27
• [Presentation] Synthesis of Novel Peptide Analog by Iterative Linkage of Squaric Acid-Containing Amino Acid (2012)
  • Author(s): K. Maeda, T. Shinada, Y. Ohfune
  • Organizer: The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
  • Place of Presentation: Kyoto, Japan
• [Presentation] スクアリン酸含有アミノ酸を組み込んだ新規ペプチドアナログ合成 (2012)
  • Author(s): 前田健太郎、木庭雄一、石田捻和、品田哲郎、大船泰史
  • Organizer: 第54回天然有機化合物討論会
• [Presentation] スクアリン酸含有アミノ酸を組み込んだ新規ペプチドアナログ合成 (2012)
  • Author(s): 前田健太郎
  • Organizer: 第54回天然有機化合物討論会
  • Place of Presentation: 東京農業工業大学
• [Presentation] Synthesis of Novel Peptide Analog by Iterative Linkage of Squaric Acid-Containing Amino Acid (2012)
  • Author(s): K. Maeda
  • Organizer: the Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
  • Place of Presentation: Kyoto
• [Presentation] Synthesis of Squaric Acid-containing Amino Acid and Its Incorporation into Peptide (2011)
  • Author(s): T.Shinada, Y.Kiniwa, Y.Ohfune
  • Organizer: 8th AFMC International Medicinal Chemistry Symposium. "Frontier of Medicinal Science"
  • Place of Presentation: Keio Plaza Hotel
  • Year and Date: 2011-12-01
• [Presentation] Iterative Linkage of α-Amino Squaric Acid (2011)
  • Author(s): K.Maeda, T.Shinada, Y.Ohfune
  • Organizer: The 16th Osaka City University International Symposium on Dynamic Molecular Devices
  • Place of Presentation: Osaka City University
  • Year and Date: 2011-11-11
• [Presentation] スクアリン酸含有アミノ酸の連続連結法の開発 (2011)
  • Author(s): 前田健太郎、品田哲郎、大船泰史
  • Organizer: 第38回有機反応懇談会
  • Place of Presentation: 大阪府立大学
  • Year and Date: 2011-08-03
• [Presentation] α-アミノスクアリン酸含有ペプチドライブラリーの合成研究 (2011)
  • Author(s): 木庭雄一
  • Organizer: 日本化学会91春季年会
  • Place of Presentation: 神奈川大学横浜キャンパス
  • Year and Date: 2011-03-28
• [Presentation] Incorporation of squaric acid containing amino acid into peptide (2011)
  • Author(s): T.Shinada
  • Organizer: The 15th Osaka City University International Conference on Spin Chemistry and Dynamic Molecular Science & Research Meeting of Dynamic Molecular Devices
  • Place of Presentation: 大阪市立大学学術情報センター10F
  • Year and Date: 2011-01-25
• [Presentation] Synthesis of Squaric Acid-containing Amino Acid and Its Incorporation into Peptide (2011)
  • Author(s): T. Shinada, Y. Kiniwa, Y. Ohfune
  • Organizer: 8th AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: Keio Plaza Hotel, Japan
• [Presentation] α-アミノスクアリン酸含有ペプチドライブラリーの合成研究 (2011)
  • Author(s): 木庭雄一、品田哲郎、大船泰史
  • Organizer: 日本化学会第91 春季年会
  • Place of Presentation: 神奈川大学横浜キャンパス
• [Presentation] Incorporation of Squaric Acid-containing Amino Acid into Peptide. (2010)
  • Author(s): T.Shinada
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (Pacifichem)
  • Place of Presentation: ハワイコンベンショナルセンター
  • Year and Date: 2010-12-29
• [Presentation] α-アミノスクアリン酸の固相ペプチド合成 (2010)
  • Author(s): 木庭雄一
  • Organizer: 第37回有機反応懇談会主催 有機反応懇談会
  • Place of Presentation: 京都大学化学研究所
  • Year and Date: 2010-08-02
• [Presentation] Incorporation of squaric acid-containing amino acid into peptide (2010)
  • Author(s): T.Shinada
  • Organizer: The 3rd International Conference of the OCU Advanced Research Institute for Natural Science and Technology (OCARINA)
  • Place of Presentation: 大阪市立大学学術情報センター10F
  • Year and Date: 2010-03-07
• [Presentation] Incorporation of Squaric Acid-containing Amino Acid into Peptide (2010)
  • Author(s): T. Shinada, Y. Kiniwa, T. Ishida, and Y. Ohfune
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Societies (Pacifichem)
  • Place of Presentation: Hawaii, USA
• [Presentation] 固相合成を指向したα-アミノスクアリン酸含有ペプチドの合成研究 (2010)
  • Author(s): 木庭雄一・品田哲郎・大船泰史
  • Organizer: 日本化学会第90年会
  • Place of Presentation: 近畿大学
• [Presentation] 精密有機合成を駆使した微量生理活性分子の構造決定 (2009)
  • Author(s): 品田哲郎
  • Organizer: 第36回有機反応懇談会
  • Place of Presentation: 関西学院大学
  • Year and Date: 2009-08-03
• [Presentation] Synthetic Study of α-Amino Squaric Acid-containing Peptide (2009)
  • Author(s): 木庭雄一・品田哲郎・大船泰史
  • Organizer: 第36回有機反応懇談会
  • Place of Presentation: 関西学院大学
  • Year and Date: 2009-08-03
• [Presentation] Synthesis of α-Amino Squaric Acid and Its Incorporation into Peptide (2009)
  • Author(s): T. Shinada, T. Ishida, A. Yamasaki, Y. Kiniwa, Y. Ohfune
  • Organizer: Tenth Tetrahedron Symposium
  • Place of Presentation: Paris, France
• [Presentation] Synthesis of α-Amino Squaric Acid and Its Incorporation into Peptide (2009)
  • Author(s): T.Shinada, T.Ishida, A.Yamasaki, Y.Kiniwa, Y.Ohfune
  • Organizer: Tenth Tetrahedron Symposium
  • Place of Presentation: フランス、パリ
• [Presentation] α-アミノスクアリン酸連結型ペプチドアナログの合成
  • Author(s): 前田健太郎
  • Organizer: 第39回有機反応懇談会
  • Place of Presentation: 関西大学
• [Presentation] Synthesis of Novel Peptide Analog by Linkage of Squaric Acid-Containing Amino Acid
  • Author(s): K. Maeda
  • Organizer: The 17th Osaka City University International Symposium
  • Place of Presentation: Osaka City University
• [Remarks]
  • URL: http://www.sci.osaka-cu.ac.jp/chem/henkan/index.html
• [Remarks] 大阪市立大学大学院理学研究科物質分子系専攻分子変換学研究室
  • URL: http://www.sci.osaka-cu.ac.jp/chem/henkan/index.html
• [Remarks]
  • URL: http://www.sci.osaka-cu.ac.jp/chem/henkan/index.html
• [Remarks]
  • URL: http://www.sci.osaka-cu.ac.jp/chem/henkan/index.html
• [Remarks]
  • URL: http://www.materials.sci.osaka-cu.ac.jp/HENKAN/index.html