Add time:08/31/2019         Source:sciencedirect.com

The aminoglycoside antibiotic butirosin (1) has been chemically modified in its amino acid side-chain. The (S)-()-4-amino-2-hydroxybutyryl side-chain was removed by alkaline hydrolysis of the tetrakis(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl) derivative. The resulting deacylated, trisubstituted derivative 3 was reacylated with a wide variety of mono and polyfunctional amino acids. The cyclohexenyl protecting groups were then removed by chlorine gas and the new analogs isolated chromatographically. Structure-activity relationships were determined with five microorganisms, including Pseudomonas aeruginosa. The specific side-chain structures that exhibited maximum potency against Pseudomonas are identified.Butirosin1, a new aminoglycoside antibiotic complex produced by mucoid strains of Bacillus circulans NRRL B-3312 and B-3313, is the first example of the aminocyclitol class of compounds to contain an amino acid in its chemical structure. Complete structural assignments for butirosin A and B have been described2 and are shown in formula 1. The amino acid, which is connected by an amide linkage to N1 of the deoxystreptamine moiety, was found to be the unique (S)-()-4-amino-2-hydroxybutyric acid2. The butirosins have marked activity against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa, both in vitro and in vivo, as well as low toxicity in mammalian species3,4. They were therefore likely candidates for structural-modification studies.

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