Directed biosynthesis of 5"-fluoropactamycin in Streptomyces pactum.
A new pactamycin analogue, 5"-fluoropactamycin, was prepared by directed biosynthesis. Supplementation of the fermentation medium of Streptomyces pactum, var. pactum with 3-amino-5-fluorobenzoic acid, an analogue of 3-aminobenzoic acid, an advanced precursor in pactamycin biosynthesis, resulted in co-production of pactamycin and the new pactamycin analogue. A similar feeding experiment with 3-amino-5-methylbenzoic acid did not result in formation of the corresponding methylated pactamycin analogue, but only in inhibition of pactamycin production. Comparison of antimicrobial and cytotoxic activities of pactamycin and 5"-fluoropactamycin showed no significant differences.
Adams
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Roger Adams Laboratory, University of Illinois at Urbana-Champaign 61801.
Rinehart
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D000818:Animals; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D007939:Leukemia L1210; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010142:Pactamycin / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013302:Streptomyces / Q000378:metabolism*
C091816:5''-fluoropactamycin; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D010142:Pactamycin