Synthesis, Antibacterial and Antiribosomal Activity of the 3C-Aminoalkyl Modification in the Ribofuranosyl Ring of Apralogs (5-O-Ribofuranosyl Apramycins)

Lubriks, Dmitrijs; Haldimann, Klara; Hobbie, Sven N; Vasella, Andrea; Suna, Edgars; Crich, David

doi:10.3390/antibiotics12010025

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Lubriks, D., Haldimann, K., Hobbie, S. N., Vasella, A., Suna, E., & Crich, D. (2022). Synthesis, Antibacterial and Antiribosomal Activity of the 3C-Aminoalkyl Modification in the Ribofuranosyl Ring of Apralogs (5-O-Ribofuranosyl Apramycins). Antibiotics, 12(1), 25. https://doi.org/10.3390/antibiotics12010025

Abstract

The synthesis and antiribosomal and antibacterial activity of both anomers of a novel apralog, 5-O-(5-amino-3-C-dimethylaminopropyl-D-ribofuranosyl)apramycin, are reported. Both anomers show excellent activity for the inhibition of bacterial ribosomes and that of MRSA and various wild-type Gram negative pathogens. The new compounds retain activity in the presence of the aminoglycoside phosphoryltransferase aminoglycoside modifying enzymes that act on the primary hydroxy group of typical 4,5-(2-deoxystreptamine)-type aminoglycoside and