SÍNTESE ENANTIOSSELETIVA E AVALIAÇÃO BIOLÓGICA DE PROLINOMIMÉTICOS DO PLG E GPE

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Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria

Publication . Costa, Margarida; Sampaio-Dias, Ivo E.; Castelo-Branco, Raquel; Scharfenstein, Hugo; Rezende de Castro, Roberta; Silva, Artur; Schneider, Maria Paula C.; Araújo, Maria João; Martins, Rosário; Domingues, Valentina F.; Nogueira, Fátima; Camões, Vera; Vasconcelos, Vitor M.; Leão, Pedro N.

Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus.

2019-02Journal article

Open access