Synthesis of the Host-specific Toxins, AK- and AF-toxin

宿主特异性毒素 AK 和 AF 毒素的合成

• 批准号: 61571007
• 负责人: IRIE Hiroshi
• 金额: $ 1.28万
• 依托单位: Nagasaki University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1986
• 资助国家: 日本
• 起止时间: 1986 至 1987
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-61571007/
• 关键词: Total synthesis of natural products; Host-specific toxins; Nijisseiki; Stereostructure; 不斉源; 植物病原菌; 宿主特異的毒性; 二十世紀黒斑病; 全合成; 不斉合成原料としてのビタミン C

Total synthesis of the methyl esters of AK-toxin II and AF-toxin IIa and IIc, the host-specific toxins for Japanease pear Nijisseiki, was accomplished by starting from Vitamin C as a chiral starting material. Investigation of biological activities of several kinds of the intermediates prepared on the course of the synthesis confirmed that the stereochemistry of two chiral centers in the trienoic acid moiety of these toxins has tight relationship with toxic properties of the toxins. Futhermore, the synthesis revealed the availability of Vitamin C to synthesis of natural products as an appropriate chiral pool.

以维生素C为手性起始原料，合成了日本梨的特异性毒素AK-毒素Ⅱ、AF-毒素Ⅱ a和Ⅱ c的甲酯。对合成过程中得到的几种中间体进行了生物活性研究，证实了三烯酸结构中两个手性中心的立体化学与毒素的毒性密切相关。因此，该合成揭示了维生素C作为合适的手性库在天然产物合成中的可用性。

项目成果

Hiroshi Irie: Chemical & Pharmaceutical Bulletin. 33. 1313-1315 (1985)

入江浩：化学

入江寛: Chemical & Pharmaceutical Bulletin. 35. 2598-2601 (1987)

Hiroshi Irie：化学与制药公报。35. 2598-2601 (1987)

Hiroshi Irie, Kohei Matsumoto, and Yong Zhang: "Synthesis of the Host-specific Toxins AF-toxin IIc and AK-toxin Congeners and their Stereostructure-Toxicity Relationship" Chemical & Pharmaceutical Bulletin. 34. 2668-2671 (1986)

Hiroshi Irie、Kohei Matsumoto 和 Yong Zhang：“宿主特异性毒素 AF-毒素 IIc 和 AK-毒素同系物的合成及其立体结构-毒性关系”化学

Hiroshi Irie, Kohei Matsumoto, Takao Kitagawa, Yong Zhang, Tamio Ueno, Tadakazu Nakashima, and Hiroshi Fukami: "Total Synthesis of Esters of AK-toxin II and AF-toxin IIc Starting from Vitamin C as a Chiral Material" Chemical & Pharmaceutical Bulletin. 35.

Hiroshi Irie、Kohei Matsumoto、Takao Kitakawa、Yong Zhu、Tamio Ueno、Tadakazu Nakashima 和 Hiroshi Fukami：“以维生素 C 作为手性材料，全合成 AK-毒素 II 和 AF-毒素 IIc 酯”化学

Hiroshi Irie: Chemical & Pharmaceutical Bulletin. 34. 2668-2671 (1986)

入江浩：化学