Urdamycins, new angucycline antibiotics from Streptomyces fradiae. VI. Structure elucidation and biosynthetic investigations on urdamycin H.
A new angucycline antibiotic has been discovered as a small side product of Streptomyces fradiae (strain Tü 2717), the producer of the urdamycin complex, during screening for biosynthetic relatives of urdamycins C and D. The structure was elucidated after isolation, via strain selection, of a mutant of S. fradiae that produces this new congener in larger amounts. The structure includes a new chromophore containing aglycone that has not been found before among the angucyclines nor as a natural product generally. In urdamycin H (1) the angucycline four-ring system is enlarged by a (p-OH-phenyl)furan moiety and is closely related to urdamycin C (2). The structure was elucidated by comparison of the physico-chemical data with those of known urdamycins, especially with those of urdamycin C (2), and was confirmed by intensive 2D NMR analysis. Biosynthetic studies showed that tyrosine and not the smaller p-OH-phenylglycine is the precursor of the (p-OH-phenyl)furan moiety.
Rohr
J
J
Institut für Organische Chemie Universität Göttingen.
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000302:isolation & purification*; D055598:Chemical Phenomena; D002621:Chemistry; D005998:Glycine / Q000378:metabolism / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000378:metabolism; D014443:Tyrosine / Q000378:metabolism
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C052535:urdamycin C; C061466:urdamycin H; D014443:Tyrosine; C023010:4-hydroxyphenylglycine; D005998:Glycine