Abstract
Gramicidin S (GS) analogs in which the Ndelta atoms of the two Orn side chains are linked by an oligomethylene bridge [-(CH2)n-; n=3-5] were prepared via the bis(p-nitrobenzenesulfonyl) derivative [Orn(NBS)2,2']GS. For comparison the nonbridged secondary amino group-containing analog [Orn(Me)2,2']GS was also prepared. 1H NMR and CD spectral analysis indicated that these analogs adopt the same beta-sheet conformation as GS. The antimicrobial activities of these analogs were very similar, but were slightly dependent on the bridge chain length, the trimethylene-bridged analog being the most potent.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry*
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Anti-Bacterial Agents / pharmacology*
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Bacillus subtilis / drug effects
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Circular Dichroism
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Drug Evaluation, Preclinical
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Escherichia coli / drug effects
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Gramicidin / analogs & derivatives*
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Gramicidin / chemistry*
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Hydrocarbons
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Magnetic Resonance Spectroscopy
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Methane / analogs & derivatives
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Methane / chemistry
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Microbial Sensitivity Tests
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Ornithine / chemistry
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Protein Conformation
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Staphylococcus aureus / drug effects
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Hydrocarbons
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Gramicidin
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carbene
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Ornithine
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Methane