3-Amino-5-hydroxybenzoic acid in antibiotic biosynthesis. VI. Directed biosynthesis studies with ansamycin antibiotics.
Biosynthesis of the ansamycin antibiotic actamycin (2) was markedly increased by the addition of the precursor 3-amino-5-hydroxybenzoic acid (1) to the producing Streptomyces fermentation. Similar addition of the 4-chloro, 6-chloro, N-methyl and O-methyl analogues 4, 6, 5 and 7 of the amino acid 1 reduced actamycin production and did not yield structurally modified ansamycins. These results with the analogues 4, 5 and 7 indicate that the corresponding chlorine, N-methyl and O-methyl substituents present in the nuclei of various ansamycins are introduced at biosynthetic stages beyond the level of the amino acid 1.
D062365:Aminobenzoates / Q000378:metabolism*; D000880:Anthraquinones / Q000096:biosynthesis; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D005285:Fermentation; D062385:Hydroxybenzoates; D047029:Lactams, Macrocyclic; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000378:metabolism*; D013329:Structure-Activity Relationship
D062365:Aminobenzoates; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D062385:Hydroxybenzoates; D047029:Lactams, Macrocyclic; C039870:actamycin; C031509:3-amino-5-hydroxybenzoic acid