New Construction of Biologically Active Substances using Diphenyl Phosphorazidate

使用叠氮二苯酯构建生物活性物质

• 批准号: 60470151
• 负责人: SHIOIRI Takayuki
• 金额: $ 2.88万
• 依托单位: Nagoya City University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1985
• 资助国家: 日本
• 起止时间: 1985 至 1986
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-60470151/
• 关键词: Peptide bond formation; Carbon-carbon bond formation; Introduction of amino groups; Cytotoxic cyclic peptides of marine origin; Amino sugars; Anthramycin antibiotics; Diphenyl phosphorazidate; 環化反応

Diphenyl phosphorazidate (DPPA, <(C_6H_5O)_2> P(O) <N_3> ) is a versatile synthetic reagent. DPPA can be used for (1) the peptide bond formation (N-acylation), (2) the carbon-carbon bond formation (C-acylation), and (3) the introduction of amino functions (amination). By use of these DPPA-mediated reactions as key steps, new construction of biologically active substances has been developed. Several antineoplastic and/or cytotoxic cyclic peptides of marine origin such as dolastatin 3, ascidiacyclamide, patellamides A, B, C, ulithiacyclamide, and ulicyclamide have been prepared using the reaction (1). The C-acylation (2) has been applied to efficient syntheses of L-daunosamine, L-vancosamine, D-ristosamine, and mugineic acid. Tilivalline has been also synthesized through the amination (3) using DPPA.

叠氮磷酸二苯酯（DPPA，&lt;（C_6H_5O）_2&gt; P（O）<N_3>）是一种用途广泛的合成试剂。DPPA可用于（1）肽键形成（N-酰化），（2）碳-碳键形成（C-酰化），和（3）氨基官能团的引入（胺化）。通过使用这些DPPA介导的反应作为关键步骤，已经开发了新的生物活性物质的构建。已经使用反应（1）制备了几种海洋来源的生物活性和/或细胞毒性环肽，例如多拉司他丁3、海鞘酰胺、patellamides A、B、C、ulithiacyclamide和ulicyclamide。C-酰化反应（2）已被应用于L-柔红霉素、L-万古胺、D-瑞斯托胺和mugineic酸的有效合成。还使用DPPA通过胺化（3）合成了替利伐林。

项目成果

Yasumasa Hamada: Tetrahedron Letters. 26. 5159-5162 (1985)

滨田康正：四面体字母。

Shinji Kato: "New Methods and Reagents in Organic Synthesis. 64. Total Synthesis of Ulithiacyclamide, a Strong Cytotoxic Cyclic Peptide from Marine Tunicates" Tetrahedron Letters. 27. 2653-2656 (1986)

Shinji Kato：“有机合成的新方法和试剂。64。Ulithiacyclamide（一种来自海洋被囊动物的强细胞毒性环肽）的全合成”四面体快报。

Yasumasa Hamada: Tetrahedron Letters. 26. 6501-6504 (1985)

滨田康正：四面体字母。

Shinji Kato: Tetrahedron Letters. 27. 2653-2656 (1986)

加藤真司：四面体字母。

Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 57. A Stereoselective Synthesis of a Derivative of D-Ristosamine" Chem. Pharm. Bull.33. 5601-5604 (1985)

Yasumasa Hamada：“有机合成中的新方法和试剂。57。D-Ristosamine 衍生物的立体选择性合成”Chem。