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Antibacterial Muraymycins from Mutant Strains of Streptomyces sp. NRRL 30471

Zheng Cui, Xiachang Wang, Stefan Koppermann, Jon S. Thorson, Christian Ducho, Steven G. Van Lanen
Journal of natural products 2018 v.81 no.4 pp. 942-948
Aquifex, Escherichia coli, Staphylococcus aureus, Streptomyces, antibacterial properties, antibiotics, fatty acids, inhibitory concentration 50, mutagenesis, mutants, nuclear magnetic resonance spectroscopy, nucleosides, spectral analysis
Muraymycins are nucleoside antibiotics isolated from Streptomyces sp. NRRL 30471 and several mutant strains thereof that were generated by random, chemical mutagenesis. Reinvestigation of two mutant strains using new media conditions led to the isolation of three new muraymycin congeners, named B8, B9, and C6 (1–3), as well as a known muraymycin, C1. Structures of the compounds were elucidated by HRMS and 1D and 2D NMR spectroscopic analyses. Complete 2D NMR assignments for the known muraymycin C1 are also provided for the first time. Compounds 1 and 2, which differ from other muraymycins by having an elongated, terminally branched fatty acid side chain, had picomolar IC₅₀ values against Staphylococcus aureus and Aquifex aeolicus MraY and showed good antibacterial activity against S. aureus (MIC = 2 and 6 μg/mL, respectively) and Escherichia coli ΔtolC (MIC = 4 and 2 μg/mL, respectively). Compound 3, which is characterized by an N-acetyl modification of the primary amine of the dissacharide core that is shared among nearly all of the reported muraymycin congeners, greatly reduced its inhibitory and antibacterial activity compared to nonacylated muraymycin C1, which possibly indicates this modification is used for self-resistance.