Evaluating indole-related derivatives as precursors in the directed biosynthesis of diazepinomicin analogues

Journal of Natural Products

Volumn 72, Issue 3, 2009, Pages 496-499

  Ratnayake, Anokha S ^a   Janso, Jeffrey E ^a   Feng, Xidong ^a   Schlingmann, Gerhard ^a   Goljer, Igor ^b   Carter, Guy T ^a  

^a WYETH RESEARCH   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 F DIAZEPINOMICIN; 3 F DIAZEPINOMICIN; ANTIINFECTIVE AGENT; DIAZEPINOMICIN; UNCLASSIFIED DRUG;

ACTINOBACTERIA; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM CULTURE; DRUG SYNTHESIS; FERMENTATION; GRAM POSITIVE BACTERIUM; MICROMONOSPORA; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SPECTROSCOPY; STAPHYLOCOCCUS AUREUS;

DIBENZAZEPINES; HYDROCARBONS, FLUORINATED; INDOLES; MICROBIAL SENSITIVITY TESTS; MICROMONOSPORA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STAPHYLOCOCCUS AUREUS;

MICROMONOSPORA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 65249180102     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800664u     Document Type: Article

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7. A preliminary study was conducted with three different precursor concentrations (0.5, 0.15, 0.075 g/L) to determine the ideal feeding dosage of the precursors with the least amount of feedback inhibition.
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15. Even though initial analytical scale (10 mL growth medium) experiments were conducted with 6-F-indole as the precursor, subsequently we discovered that a relatively higher production of 3-F-diazepinomicin (3) could be achieved in the presence of 6-F-tryptophan (3a). Therefore, scale-up fermentations were carried out with 6-F-tryptophan as the precursor.
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18. The solubilization of the precursors was closely monitored visually. Heating and sonication were performed until no particulates remained in the medium. Efficient solubilization was confirmed by HPLC-UV- MS analysis of each sample at time zero (before inoculation).