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

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 () 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 was more active than amikacin.