Chemical Conversion of Anthramycin 11-Methyl Ether to Didehydroanhydroanthramycin and Its Utilization in Studies of the Biosynthesis and Mechanism of Action of Anthramycin

Publisher Website
Google Scholar
Abstract
Reaction of anthramycin 11-methyl ether (AME) with trifluoroacetic acid results in formation of (1,11a)-didehydroanhydroanthramycin (DAA). Anthramycin biosynthetically labeled 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 labeling pattern of 3''-tritiated species of tyrosine in AME. As expected negligible losses of tritium occurred from AME biosynthetically labeled from L-[2- or 6-3H] or L-[3- or 5-3H]tyrosine. DAA did not form a stable adduct with [calf thymus] DNA in accord with the postulated mechanism of antitumor action of anthramycin.