ABSTRACT
An actinomycete strain No. B-52653 was found to produce an antibiotic selectively active against the in vitro antibiotic resistant mutant of Staphylococcus aureus. Based on taxonomic studies, the name Streptomyces albulus subsp. ochragerus subsp. nov. is proposed for the strain. The microorganism produced two kinds of antibiotics; one identical with gougerotin, the other an amphoteric water soluble dipeptide containing L-alanine. The latter has the molecular formula C9H15N3O6 and is named alahopcin. It has a broad antibacterial spectrum and a synergistic effect with some other antibiotics against some antibiotic resistant staphylococci. Alahopcin has a low toxicity and was effective against experimental infections in mice caused by Staphylococcus aureus.
Subject(s)
Anti-Bacterial Agents , Anti-Bacterial Agents/isolation & purification , Dipeptides/isolation & purification , Peptides , Streptomyces/metabolism , Animals , Anti-Bacterial Agents/pharmacology , Antimicrobial Cationic Peptides , Bacteria/drug effects , Chemical Phenomena , Chemistry , Dipeptides/pharmacology , Fermentation , Male , Mice , Mice, Inbred ICRABSTRACT
An aziridine ring-formation involving the reaction of adjacent amino and alcohol groups with triphenylphosphine, carbon tetrachloride, and triethylamine was applied at the 2' and 3' positions of butirosin A (1a) and B (1b). The amino groups at the 2' position of 1a and 1b were p-methoxybenzylated to increase the nucleophilicity of the nitrogen atom and to avoid the formation of a P-N linkage, and the N-p-methoxybenzyl derivatives were converted into the aziridine derivatives, which were then subjected to hydrogenolysis and removal of the protecting groups to give 3'-deoxybutirosin A (7a) and B (7b), respectively. This new method is compared with the conventional N,O-protecting method that involves several complex steps.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Butirosin Sulfate/chemical synthesis , Bacteria/drug effects , Butirosin Sulfate/pharmacology , Methods , Microbial Sensitivity TestsABSTRACT
A new aminoglycoside antibiotic was isolated from the fermentation broths of two strains of Bacillus species. The antibiotic is active against gram-positive and some gram-negative bacteria, and its antimicrobial spectrum is similar to that of ribostamycin. The chemical structure was determined to be 5-beta-d-xylofuranosylneamine, which is identical to the deacylated product obtained from butirosin A.
