Semisynthetic aminoglycoside antibacterials. Part 10. Synthesis of novel 1-N-aminoalkoxycarbonyl and 1-N-aminoalkylcarboxamido derivatives of sisomicin, gentamicin B, gentamicin C1a, and kanamycin A

Abstract

Suitably protected derivatives of sisomicin, 5-epi-sisomicin, gentamicin B, gentamicin C_1a, and kanamycin A have been converted into a series of 1-N-alkoxycarbonyl, 1-N-alkoxycarbonyl, 1-N-carboxamido, 1-N-alkylcarboxamido, and 1-N-aminoalkylcarboxamido derivatives. Representative thio-analogues have also been prepared. ¹³C N.m.r. studies have revealed that these novel semisynthetic aminoglycosides have different solution conformations about the C-6–O glycosidic bond relative to the parent aminoglycosides from which they are derived.