Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum.
The biosynthesis of the antitumor antibiotic sibiromycin by Streptosporangium sibiricum requires the construction of four units: the amino sugar from glucose; the anthranilate ring from DL-tryptophan probably via kynurenine; the aromatic methyl group from methionine; the propylidene proline from L-tyrosine with the loss of two aromatic carbons and addition of a C-1 from methionine. Retention of tritium from DL-[5-3H]tryptophan in sibiromycin suggest an NIH shift during hydroxylation of an intermediate.
D000192:Actinomycetales / Q000378:metabolism*; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis*; D002250:Carbon Radioisotopes; D007553:Isotope Labeling; D008715:Methionine / Q000378:metabolism; D013329:Structure-Activity Relationship; D014316:Tritium; D014364:Tryptophan / Q000378:metabolism; D014443:Tyrosine / Q000378:metabolism
D000903:Antibiotics, Antineoplastic; D002250:Carbon Radioisotopes; D014316:Tritium; D014443:Tyrosine; D014364:Tryptophan; D008715:Methionine