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The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.

ABSTRACT: 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.

SUBMITTER: Hughes CC 

PROVIDER: S-EPMC2820876 | biostudies-literature | 2008 Feb

REPOSITORIES: biostudies-literature

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The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.

Hughes Chambers C CC   Prieto-Davo Alejandra A   Jensen Paul R PR   Fenical William W  

Organic letters 20080119 4

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  ...[more]

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