1- AND 3-DEAMIDINO DERIVATIVES OF DIHYDROSTREPTOMYCIN AND SOME 1-N-ACYL DERIVATIVES

Abstract

1-Deamidino-, 3-deamidino- and 1, 3-di(deamidino)dihydrostreptomycin (1, 2, 3) were prepared by treatment of dihydrostreptomycin (DHSM) with ammonia at 100°C. The 3-guanidino group of DHSM is suggested to be more important than the 1-guanidino group for the antibacterial activity of DHSM. 1-N-[(S)-4-Amino-2-hydroxybutyryl] and 1-N-[(S)-4-guanidino-2-hydroxybutyryl] derivatives (4, 6) of 1-deamidinodihydrostreptomycin were further prepared.