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加勒比西瓜毒素C-CTX1及其C3-Epimer的融合总合成

Makoto Sasaki¹, Atsushi Umehara¹, Kohtaro Sugahara²

¹Graduate School of Life Sciences, Tohoku University, Katahira, Aoba-ku, Sendai 980-8577, Japan.

Journal of the American Chemical Society

|March 9, 2026

概括

研究人员合成了加勒比海的ciguatoxin C-CTX1,一种强烈的毒素,引起ciguatera鱼的中毒. 这一突破提供了结构确认和进一步研究其神经毒性的访问.

科学领域:

海洋天然产品化学化学
合成有机化学合成有机化学
神经毒理学神经毒理学

背景情况:

加勒比海的ciguatoxin C-CTX1 (C-CTX1) 是一种强大的多环乙烯毒素,负责ciguatera鱼类中毒.
在加勒比海以外已检测到C-CTX1,但其复杂的结构和自然稀缺性阻碍了充分的验证.
之前的研究缺乏对C-CTX1结构和生物特性的最终化学确认.

研究的目的:

为了实现第一个C-CTX1及其C3-epimer的全合成.
通过化学合成提供最终的结构确认.
为进一步研究提供实用,毫克尺度的C-CTX1epimers访问.

主要方法:

收的碎片合策略. 融合的碎片合策略.
合成涉及加入ABCDE和HIJKLMN环单元.
晚期的激素循环和环闭转化被用于FG环结构.

主要成果:

成功完成了C-CTX1及其C3-epimer的总合成.
这两种化合物的最终结构确认.
现在可以获得C-CTX1及其表皮质的毫克级量.
对比生物评估显示,epimer之间神经毒性的显著差异.

结论:

总合成验证了C-CTX1.1的结构.
合成途径为毒理学研究提供了至关重要的C-CTX1及其表皮质的访问权.
神经毒性的显著差异凸显了立体化学在C-CTX1生物活性中的重要性.

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