C-N-Coupled Metabolites Yield Insights into Dynemicin A Biosynthesis.

ABSTRACT: The biosynthesis of the three structural subclasses of enediyne antitumor antibiotics remains largely unknown beyond a common C₁₆ -hexaene precursor. For the anthraquinone-fused subtype, however, an unexpected iodoanthracene γ-thiolactone was established to be a mid-pathway intermediate to dynemicin A. Having deleted a putative flavin-dependent oxidoreductase from the dynemicin biosynthetic gene cluster, we can now report four metabolites that incorporate the iodoanthracene and reveal the formation of the C-N bond linking the anthraquinone and enediyne halves emblematic of this structural subclass. The coupling of an aryl iodide and an amine is familiar from organometallic chemistry, but has little or no precedent in natural product biosynthesis. These metabolites suggest furthe

SUBMITTER: Cohen DR 

PROVIDER: S-EPMC7685002 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature