Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

The synthesis of eleven novel antibacterial agents is reported. The structures are based on a C2-symmetric binaphthyl scaffold which holds two identical chains consisting of a short linker, a basic amino acid and a small hydrophobic side chain. Antibacterial activity is revealed for a number of derivatives down to an MIC of 2 μg/mL (2 μM) against Staphylococcus aureus – comparable to vancomycin, and an MIC of 31 μg/mL (31 μM) against some vancomycin-resistant enterococcal strains.

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► Novel C2-symmetric binaphthyl scaffolded peptides.
► Antibacterial activity at therapeutic levels against S. aureus.
► Significant activity against vancomycin-resistant strains.