Probing the functional requirements of the L-haba side-chain of amikacin - Synthesis, 16S A-site rRNA binding, and antibacterial activity

Article abstract of DOI:10.1016/S0040-4020(02)01625-3

The l-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin.