Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo, 060-0812, Japan.
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.
Chembiochem. 2020 Dec 1;21(23):3329-3332. doi: 10.1002/cbic.202000409. Epub 2020 Aug 25.
Kasumigamide is an antialgal hybrid peptide-polyketide isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-87). The biosynthetic gene cluster was identified from not only the cyanobacterium but also Candidatus "Entotheonella", associated with the Japanese marine sponge Discodermia calyx. Therefore, kasumigamide is considered to play a key role in microbial ecology, regardless of the terrestrial and marine habitats. We now report synthetic studies on this intriguing natural product that have led to a structural revision and the first total synthesis. During this study, a new analogue, deoxykasumigamide, was also isolated and structurally validated. This study confirmed the presence of the unusual pathway in the biosynthesis of a hybrid peptide-polyketide natural product.
卡斯米加肽是一种从淡水蓝藻铜绿微囊藻（NIES-87）中分离得到的抗藻杂肽-聚酮化合物。该生物合成基因簇不仅在蓝藻中被鉴定出来，而且还在与日本海洋海绵Discodermia calyx 相关的“Entotheonella”中被鉴定出来。因此，无论在陆地还是海洋生境中，卡斯米加肽都被认为在微生物生态学中发挥着关键作用。我们现在报告了对这一有趣的天然产物的合成研究，这些研究导致了结构修订和首次全合成。在这项研究中，还分离并结构验证了一种新的类似物，去氧卡斯米加肽。这项研究证实了杂肽-聚酮天然产物生物合成中存在不寻常途径的存在。
