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Total Synthesis and Structural Revision of Kasumigamide, and Identification of a New Analogue
Author(s) -
Kuranaga Takefumi,
Matsuda Kenichi,
Takaoka Masachika,
Tachikawa Chisato,
Sano Ayae,
Itoh Kosei,
Enomoto Ayumu,
Fujita Kei,
Abe Ikuro,
Wakimoto Toshiyuki
Publication year - 2020
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.202000409
Subject(s) - polyketide , natural product , gene cluster , biosynthesis , nonribosomal peptide , total synthesis , cyanobacteria , biomimetic synthesis , biology , polyketide synthase , stereochemistry , computational biology , chemistry , gene , biochemistry , bacteria , genetics
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.