Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University , 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.
J Nat Prod. 2012 Nov 26;75(11):2003-6. doi: 10.1021/np300604w. Epub 2012 Nov 6.
Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring system was found to be antipodal to that of karlotoxin 2, a structurally related compound recently isolated from the dinoflagellate Karlodinium veneficum. By extensive degradation of the natural product and conversion of the resulting alcohol to an MTPA ester, the absolute configuration at C45 of AM3 was confirmed to be R, supporting the originally proposed structure.
Amphidinol 3（AM3）是从甲藻属 Amphidinium klebsii 中分离得到的一种膜活性物质，由含有 25 个手性中心的长碳链组成。尽管通过广泛的 NMR 分析和天然产物的降解确定了 AM3 的绝对构型，但与最近从甲藻属 Karlodinium veneficum 中分离得到的结构相关化合物 karlotoxin 2 的四氢吡喃环系统相对应的部分结构被发现为对映体。通过对天然产物的广泛降解以及将生成的醇转化为 MTPA 酯，可以确定 AM3 的 C45 绝对构型为 R，这支持了最初提出的结构。
