Structures, reactivities, and antibiotic properties of the marinopyrroles A-F.
J Org Chem
; 75(10): 3240-50, 2010 May 21.
Article
em En
| MEDLINE
| ID: mdl-20405892
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Pirróis
/
Staphylococcus aureus
/
Antibacterianos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2010
Tipo de documento:
Article
País de afiliação:
Estados Unidos