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Structure, Synthesis of Hierridin C and Discovery of Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria
preprintsubmitted on 14.09.2018, 19:26 and posted on 18.09.2018, 14:55 by Margarida Costa, Ivo E. Sampaio-Dias, Raquel Castelo-Branco, Hugo Scharfenstein, Roberta Rezende de Castro, Artur Silva, Maria Paula Cruz Schneider, Maria João Araújo, Rosário Martins, Valentina F. Domingues, Fatima Nogueira, Vera Camões, Vitor M. Vasconcelos, Pedro Leao
Small, single-celled planktonic cyanobacteria are ubiquitous in the world’s oceans yet tend not to to be perceived as biosynthetically-prolific organisms. Here we report the isolation and structure elucidation of hierridin C, an antiplasmodial halogenated alkylresorcinol produced in very low amounts by the picocyanobacterium Cyanobiumsp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely-produced hierridins that relies on a key, highly 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, Cyanobiumand Synechococcus.