Open AccessPREPARATION OF FOUR NEW ANTIBIOTICS FROM A MUTANT OF Streptomyces fradiae
Author(s) -
W. Thomas Shier,
Kenneth L. Rinehart,
David Gottlieb
Publication year - 1969
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.63.1.198
Subject(s) - streptomyces fradiae , aminocyclitol , antibiotics , mutant , neomycin , streptomyces , stereochemistry , chemistry , tylosin , aminoglycoside , biochemistry , biology , actinomycetales , bacteria , genetics , gene
A mutant ofStreptomyces 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 withN -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.