Preparation of four new antibiotics from a mutant of Streptomyces fradiae.
A mutant of Streptomyces fradiae 3535 incapable of synthesizing the antibiotic neomycin in the absence of added deoxystreptamine, the aminocyclitol subunit of the antibiotic, has been isolated from a culture treated with N-methyl-N'-nitro-N-nitrosoguanidine. The related aminocyclitols streptamine and 2-epistreptamine, both available by chemical synthesis, were incorporated by the mutant strain into four new antibiotics, for which we suggest the names hybrimycins A (isomers 1 and 2, from streptamine) and hybrimycins B (isomers 1 and 2, from 2-epistreptamine). Structures of the new antibiotics were established from the mass spectral, nuclear magnetic resonance, and optical rotatory properties of appropriate derivatives. This method offers a promising approach to the synthesis of other antibiotics.
D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008956:Models, Chemical; D009154:Mutation; D009905:Optical Rotatory Dispersion; D013302:Streptomyces / Q000378:metabolism
D000900:Anti-Bacterial Agents