Preparation and evaluation of diaminopimelic acid derivatives as multifunctional pharmaceutical materials

• Project/Area Number: 20790104
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Drug development chemistry
• Research Institution: Tohoku Pharmaceutical University
• Principal Investigator: SAITO Yukako Tohoku Pharmaceutical University, 薬学部, 助手 (30364409)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2008: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 有機化学 / アミノ酸 / クロスメタセシス反応 / 生理活性 / 自然免疫

Research Abstract

A naturally occurring amino acid, meso-diaminopimelic acid (meso-DAP) is also an essential component of the peptidoglycan of most pathogenic bacteria and has been studied extensively on the innate immune response. We describe (1) straightforward synthesis of meso-DAP (2) functional group-containing meso-DAP derivatives (3) synthesis of meso-DAP-containing peptides.

Research Products

• [Journal Article] Chemoselective (2010)
  • Author(s): Saito, Y., Yoshimura, Y., Takahata, H.
  • Journal Title: O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst, Tetrahedron Lett. 51 Pages: 6915-6917
  • Peer Reviewed
• [Journal Article] Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquino line as a novel organocatalyst (2010)
  • Author(s): Saito, Y.; Yoshimura, Y.; Takahata, H.
  • Journal Title: Tetrahedron Letters Volume: 51 Pages: 6915-6917
  • Peer Reviewed
• [Journal Article] Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-di-hydroisoquinoline (BBDI) (2008)
  • Author(s): Saito, Y., Ouchi, H., Takahata, H.
  • Journal Title: without base Tetrahedron 64 Pages: 11129-11135
  • Peer Reviewed
• [Journal Article] Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbo nyl-1,2-dihydroisoquinoline (BBDI) without base (2008)
  • Author(s): Saito, Y. ; Ouchi, H. ; Takahata, H.
  • Journal Title: Tetrahedron 64 Pages: 11129-11135
  • Peer Reviewed
• [Presentation] クロスメタセシス反応を用いた官能基導入meso-ジアミノピメリン酸の合成研究 (2011)
  • Author(s): 日本薬学会第131年会
  • Organizer: 斎藤有香子, 吉村祐一, 高畑廣紀
  • Place of Presentation: 静岡
  • Year and Date: 2011-03-31
• [Presentation] クロスメタセシス反応を用いた官能基導入meso-ジアミノピメリン酸の合成研究 (2011)
  • Author(s): 斎藤有香子, 吉村祐一, 高畑廣紀
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: 静岡
• [Presentation] Synthesis of meso-diaminopimelic acid and its application to the biologically active peptides (2010)
  • Author(s): Yukako Saito, Tomokazu Watanabe, Yuichi Yoshimura, Hiroki Takahata
  • Organizer: Pacifichem 2010
  • Place of Presentation: Honolulu, Hawaii, U.S.A.
  • Year and Date: 2010-12-19
• [Presentation] Synthesis of meso-diaminopimelic acid and its application to the biologically active peptides (2010)
  • Author(s): Yukako Saito, Tomokazu Watanabe, Yuichi Yoshimura, Hiroki Takahata
  • Organizer: Pacifichem 2010
  • Place of Presentation: Hawaii, U.S.A.
• [Presentation] 6.7-ジメトキシイソキノリンを有機触媒とするフェノール類のBoc化反応 (2010)
  • Author(s): 斎藤有香子, 吉村祐一, 高畑廣紀
  • Organizer: 第3回有機触媒シンポジウム
  • Place of Presentation: 仙台
• [Presentation] 電子供与基置換イソキノリンを触媒とするフェノール類のBoc化反応 (2010)
  • Author(s): 齋藤有香子, 吉村祐一, 高畑廣紀
  • Organizer: 日本プロセス化学会2010サマーシンポジウム
  • Place of Presentation: 東京
• [Presentation] イソキノリン類を触媒として用いるフェノール類のBoc化反応 (2010)
  • Author(s): 斎藤有香子, 吉村祐一, 高畑廣紀
  • Organizer: 日本薬学会第130年会
  • Place of Presentation: 岡山
• [Presentation] mrso-ジアミノピメリン酸誘導体の合成研究 (2009)
  • Author(s): 斎藤有香子、佐藤祐美、今堀龍志、吉村祐一、高畑廣紀
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
  • Year and Date: 2009-03-27
• [Presentation] クロスメタセシス反応を用いるmeso-ジアミノピメリン酸誘導体の合成とその応用 (2009)
  • Author(s): 斎藤有香子, 佐藤祐美, 今堀龍志, 吉村祐一, 高畑廣紀
  • Organizer: 第35回反応と合成の進歩シンポジウム
  • Place of Presentation: 金沢
• [Presentation] meso-ジアミノピメリン酸誘導体の合成研究 (2009)
  • Author(s): 齋藤有香子, 佐藤祐美, 今堀龍志, 吉村祐一, 高畑廣紀
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都
• [Presentation] meso-ジアミノピメリン酸類の新規合成法の開発と生理活性ペプチド合成への応用 (2008)
  • Author(s): 斎藤有香子, 渡辺公和, 佐藤祐美, 今堀龍志, 吉村祐一, 高畑廣紀
  • Organizer: 第50回天然有機化合物討論会
  • Place of Presentation: 福岡
• [Remarks]
  • URL: http://www.tohoku-pharm.ac.jp/laboratory/bunsiya/
• [Remarks]
  • URL: http://www.tohoku-pharm.ac.jp/laboratory/bunsiya/index.html