Chemical conversion of anthramycin 11-methyl ether to didehydroanhydroanthramycin and its utilization in studies of the biosynthesis and mechanism of action of anthramycin.
Reaction of anthramycin 11-methyl ether (AME) with trifluoroacetic acid results in formation of (1,11a)-didehydroanhydroanthramycin (DAA). Anthramycin biosynthetically labelled from DL-[3'RS(3'-3H)]; DL-[3'S(3'-3H)] and DL-[3'R(3'-3H)] tyrosine each lose approximately 50% of their tritium during this conversion to DAA confirming the labelling pattern of 3'-tritiated species of tyrosine in AME. As expected negligible losses of tritium occurred from AME biosynthetically labelled fron L-[2- or 6-3H] or L-[3- or 5-3H]tyrosine. DAA did not form a stable adduct with DNA in accord with the postulated mechanism of action of anthramycin.
D000818:Animals; D000876:Anthramycin / Q000031:analogs & derivatives / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000378:metabolism*; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000378:metabolism*; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000378:metabolism; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D014443:Tyrosine
D001570:Benzodiazepinones; D000876:Anthramycin; D014443:Tyrosine; C029811:anthramycin 11-methyl ether; C029810:1,11a-didehydroanhydroanthramycin; D004247:DNA