Open Access1- and 3-Deamidino derivatives of dihydrostreptomycin and some 1-N-acyl derivatives.
Author(s) -
Takayuki Usui,
Tsutomu Tsuchiya,
Sumio Umezawa
Publication year - 1978
Publication title -
journal of antibiotics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 80
eISSN - 1881-1469
pISSN - 0021-8820
DOI - 10.7164/antibiotics.31.991
Subject(s) - dihydrostreptomycin , chemistry , stereochemistry , antibiotics , biochemistry , streptomycin
1-Deamidino-, 3-deamidino- and 1,3-di(deamidino)dihydrostreptomycin (1, 2, 3) were prepared by treatment of dihydrostreptomycin (DHSM) with ammonia at 100 degrees 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 futher prepared.