Structures, reactivities, and antibiotic properties of the marinopyrroles A-F

Citation:
Hughes, CC, Kauffman CA, Jensen PR, Fenical W.  2010.  Structures, reactivities, and antibiotic properties of the marinopyrroles A-F. Journal of Organic Chemistry. 75:3240-3250.

Date Published:

May

Keywords:

catalyzed n-arylation, chlorination, efficient, metabolites, nitrogen nucleophiles, pyoluteorin, pyrroles, resistance, sequence-analysis, staphylococcus-aureus

Abstract:

Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.

Notes:

n/a

Website

DOI:

10.1021/jo1002054