Urdamycins, new angucycline antibiotics from Streptomyces fradiae. IV. Biosynthetic studies of urdamycins A-D.
The biogenetic origin of the angucycline antibiotics urdamycins A-D was studied by feeding experiments with isotope labeled precursors and by NMR analysis. Feeding experiments with [1-13C]acetate and [1,2-13C2]acetate show that the chromophores of urdamycins A and B and the angucycline 4-ring skeleton of the urdamycins C and D chromophores are formed from a single decapolyketide chain. The chromophores of the urdamycins C and D contain additional structural elements which derived from the amino acids tyrosine and tryptophan, respectively. The latter was shown by feeding deuterium-labeled tyrosine and 13C-labeled tryptophan derivatives. Feeding of [1-13C]glucose and of [U-13C3]glycerol proved that the C-glycosidic moiety and the three sugars (2 x L-rhodinose, 1 x D-olivose each) of the urdamycins arise from glucose. Experiments with 14C-labeled urdamycin A, obtained by biosynthesis from [14C]acetate, showed this compound to be a late precursor of the urdamycins C and D.
Rohr
J
J
Institut für Organische Chemie, Universität Göttingen, West Germany.
Beale
J M
JM
Floss
H G
HG
D000085:Acetates / Q000378:metabolism; D000617:Aminoglycosides; D000880:Anthraquinones / Q000096:biosynthesis; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005285:Fermentation; D005947:Glucose / Q000378:metabolism; D005990:Glycerol / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013302:Streptomyces / Q000378:metabolism*; D014364:Tryptophan / Q000031:analogs & derivatives / Q000378:metabolism; D014443:Tyrosine / Q000378:metabolism; D000095602:Angucyclines and Angucyclinones
D000085:Acetates; D000617:Aminoglycosides; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D005947:Glucose; D005990:Glycerol; D014364:Tryptophan; D014443:Tyrosine; C052535:urdamycin C; C052536:urdamycin D; C051487:urdamycin B; C028129:tryptophan methyl ester; C046608:kerriamycin B; D000095602:Angucyclines and Angucyclinones