Isolation and structure determination of novamethymycin, a new bioactive metabolite of the methymycin biosynthetic pathway in Streptomyces venezuelae.
Novamethymycin (9), a novel macrolide antibiotic, was isolated from Streptomyces venezuelae, the producer of methymycin (4) and neomethymycin (5). Spectroscopic analysis of 9 indicated that it is highly related to 4 and 5 but contains hydroxy groups at both C-10 and C-12 on the macrolactone ring. Bioconversion studies using the PikC cytochrome P450 hydroxylase demonstrated that 4 is converted to 9, further broadening the remarkable substrate flexibility of this enzyme.
Zhang
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Department of Microbiology and Biotechnology Institute, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Sherman
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D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D018942:Macrolides; D006899:Mixed Function Oxygenases / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D018942:Macrolides; C442771:novamethymycin; C008517:methymycin; C008594:neomethymycin; D003577:Cytochrome P-450 Enzyme System; D006899:Mixed Function Oxygenases; C442772:PikC cytochrome P450 hydroxylase