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The Marinopyrroles, Antibiotics of an Unprecedented Structure Class from a Marine Streptomyces sp.

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posted on 2008-02-21, 00:00 authored by Chambers C. Hughes, Alejandra Prieto-Davo, Paul R. Jensen, William Fenical
Cultivation of an obligate marine Streptomyces strain has furnished the marinopyrroles A and B, densely halogenated, axially chiral metabolites that contain an uncommon bispyrrole structure. X-ray analysis of marinopyrrole B showed that the natural product exists as an atropo-enantiomer with the M-configuration. Though configurationally stable at room temperature, M-(−)-marinopyrrole A can be racemized at elevated temperatures to yield the non-natural P-(+)-atropo-enantiomer. The marinopyrroles possess potent antibiotic activities against methicillin-resistant Staphylococcus aureus.