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. 2008 Feb 21;10(4):629-31.
doi: 10.1021/ol702952n. Epub 2008 Jan 19.

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

Chambers C Hughes  1 , Alejandra Prieto-Davo, Paul R Jensen, William Fenical
Affiliations

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

Chambers C Hughes et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
The marinopyrroles A (1) and B (2).
Figure 2
Figure 2
X-ray drawing of 2, depicting its absolute configuration. The hydrogen bond between the perihydroxyl group and the carbonyl is apparent.
Figure 3
Figure 3
CD spectra of 1, 2, and non-natural P-1 in acetonitrile.
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