Chemical synethesis of marine cyclic peptides for elucidation of their stereostrutures and biological activities.

海洋环肽的化学合成，用于阐明其立体结构和生物活性。

• 批准号: 20510204
• 负责人: SUENAGA Kiyotake
• 金额: $ 3万
• 依托单位: Keio University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2008
• 资助国家: 日本
• 起止时间: 2008 至 2010
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-20510204/
• 关键词: 環状ペプチド; 立体構造; Palau'amide; aurilide; miuraenamide; プロヒビチン; アクチン; 生物活性; 合成研究; オーリライド; 環状デプシペプチド; プロヒビチチン; ビセブロモアミド; 構造活性相関; パラオアミド; ディスコキオライドB; Lyngbya sp.; hexamollamide

To determine the absolute stereochemistry of palau'amide we synthesized four possible diasteremers of palau'amide with regard to C37 and C38. Among the NMR spectra of the four synthetic diastereomers, that of 1 was identical to that of natural palau'amide. This established the complete stereostructure. SAR study of aurilide was carried out, and target biomolecule of aurilide was determined to be prohibitin in the mitochondria. Synthetic studies on miuraenamide have been carried out. Miuraenamide induces actin polymerization and stabilizes actin filament. In addition, isolation, structure determination, and synthetic studies of related compounds have been carried out.

为了确定帕劳酰胺的绝对立体化学，我们合成了关于 C37 和 C38 的四种可能的帕劳酰胺非对映体。在四种合成非对映异构体的NMR谱中，1的NMR谱与天然帕劳酰胺的NMR谱相同。这就建立了完整的立体结构。对aurilide进行了SAR研究，确定aurilide的靶生物分子为线粒体中的抑制素。已经进行了 Miuraenamide 的合成研究。 Miuraenamide 诱导肌动蛋白聚合并稳定肌动蛋白丝。此外，还开展了相关化合物的分离、结构测定和合成研究。

项目成果

沖縄産ホヤDidemnum molle由来の新規ヘキサペプチドの単離と構造決定

冲绳海鞘 Didemnum molle 中新型六肽的分离和结构测定

• 发表时间: 2008
• 作者: 佐々木宏明;照屋俊明;末永聖武
• 通讯作者: 末永聖武

Marine Natural Product Aurilide Activates the OPA1-Mediated Apoptosis by Binding to Prohibitin

• DOI: 10.1016/j.chembiol.2010.10.017
• 发表时间: 2011-01-28
• 期刊: CHEMISTRY & BIOLOGY
• 作者: Sato, Shin-ichi;Murata, Asako;Uesugi, Motonari
• 通讯作者: Uesugi, Motonari

Revised Structure and Structure-Activity Relationship of Bisebromoamide and Structure of Norbisebromoamide from the Marine Cyanobacterium

海洋蓝藻双司溴酰胺和去甲司溴酰胺结构的修订结构和构效关系

• 发表时间: 2011
• 期刊: Lyngbya sp.Tetrahedron 67(5)
• 作者: Hiroaki Sasaki;Toshiaki Teruya;Hidesuke Fukazawa;Kiyotake Suenaga
• 通讯作者: Kiyotake Suenaga

Synthesis and cytotoxicity of aurilide analogs

• DOI: 10.1016/j.bmcl.2008.06.035
• 发表时间: 2008-07-15
• 期刊: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
• 影响因子: 2.7
• 作者: Suenaga, Kiyotake;Kajiwara, Shuri;Kigoshi, Hideo
• 通讯作者: Kigoshi, Hideo

Synthesis of palau'amide and its diastereomers: confirmation of its stereostructure

• DOI: 10.1016/j.tetlet.2009.10.059
• 发表时间: 2009-12-30
• 期刊: TETRAHEDRON LETTERS
• 影响因子: 1.8
• 作者: Sugiyama, Hirokazu;Watanabe, Atsushi;Suenaga, Kiyotake
• 通讯作者: Suenaga, Kiyotake