Roseophilin is a prodiginine-like compound isolated from <i>Streptomyces griseoviridis </i>displaying potential anticancer properties and a complex structure. In recent years, the Thomson group has been making progress on elucidating the biosynthesis of roseophilin. The biosynthesis of similar cyclic prodiginines involving the cyclization of an acyclic precursor has been elucidated. Based on the presence of a prodiginine biosynthetic gene cluster in <i>S. griseoviridis, </i>a biosynthetic pathway for roseophilin has been proposed involving novel prodiginine structures. In the Thomson group, two of these proposed precursors to roseophilin, 11-methyldodecylprodiginine and prodigiosin R3, have been synthesized for enzymatic feeding studies. Furthermore, our group is investigating the cyclization of a proposed radical intermediate based on prodigiosin R3, to produce the dechlorinated form of roseophilin in a biomimetic fashion. To achieve this, a precursor to the proposed radical intermediate itself and a model molecule of this precursor have both been synthesized, and cyclization to the fused macrocyclic structure will be attempted. The success or complications that arise from this process will provide insights into the cyclization of the proposed radical intermediate in nature.

Investigations into the biosynthesis of roseophilin

2019 Fall National Meeting

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