Total Synthesis and Structural Revision of Kasumigamide, and Identification of a New Analogue.

Chembiochem : a European Journal of Chemical Biology
Takefumi KuranagaToshiyuki Wakimoto

Abstract

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.

References

Sep 16, 2000·The Journal of Organic Chemistry·K Ishida, M Murakami
Mar 19, 2013·Journal of the American Chemical Society·Takefumi KuranagaMasayuki Inoue
Jun 30, 2014·Nature Chemical Biology·Toshiyuki WakimotoIkuro Abe
Mar 1, 2017·Organic Letters·Takefumi KuranagaToshiyuki Wakimoto
Jun 5, 2018·Chemical & Pharmaceutical Bulletin·Takefumi KuranagaToshiyuki Wakimoto

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