Pentabromopseudillin (PBP) and 2,3,5,7-tetrabromobenzofuro[3,2-b] pyrolle (BFP) are highly brominated pyrrole natural products isolated from marine bacteria <i>Pseudoalteromonas sp.</i> Both are known to have potent antibacterial activities againt methicillin-resistant <i>Staphylococcus aureus </i>(MRSA) and represent a novel structural scaffold compared to previously available therapeutics. In order to determine whether PBP is a biosynthetic precursor to BFP and provide a facile access to this novel pyrrole alkaloid, BFP, its biomimtic synthesis was envisioned through two routes from PBP. First, PBP was synethsized through Suzuki-Miyaura coupling with a MIDA boronate ester of pyrrole. For the conversion of PBP to BFP, the required phenolic cyclization was envisioned through both chemical and biocatalytic approaches. A cytochrome P450 enzyme (bmp7) involved in the biosynthesis of PBP in the marine bacteria will be engineered through a directed evolution approach to be applied to the synethesis of BFP and other natural products possessing challenging nucleophile-pyrrole bonds. Presented herein are our efforts and progress towards the synthesis of BFP through both approaches.

Nucleophilic substitution of 3-bromopyrrole through chemical and biocatalytic approaches towards brominated pyrrole alkaloids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.