Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 45, Pages 7420-7431Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901256
Keywords
Antibiotics; Muraymycins; Medicinal chemistry; Natural products; Peptide synthesis; Solid-phase synthesis
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG) [DU 1095/5-1]
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Naturally occurring muraymycin nucleoside antibiotics represent a promising class of novel antimicrobials as they inhibit MraY, an enzyme involved in bacterial cell wall biosynthesis. The synthesis of muraymycins and their analogues is challenging as it involves multi-step routes, thus hampering detailed structure-activity relationship (SAR) studies. In this work, we report a novel solid phase-based synthetic strategy for accessing muraymycin analogues via a modular approach, thereby enabling a more efficient access to structural variations, particularly of the muraymycin peptide moiety. The efficiency of this new method was exemplified in an alanine scan of the peptide unit. The inhibitory in vitro activities of the resultant analogues towards MraY provided novel SAR insights. Overall, this new synthetic method for the preparation of muraymycin analogues might support the development of these antibacterial agents towards potential drug candidates.
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