Summary: In the presence of S-adenosyl--methionine, cell-free extracts of sp. C5, ATCC 29050, ATCC 31913 and ATCC 31276 -methylated carminomycin and 13-dihydrocarminomycin to daunomycin and 13-dihydrodaunomycin, respectively. With the corresponding aglycones, carminomycinone and 13-dihydrocarminomycinone, as substrates, no methylated products were detected. Other 4-hydroxyanthracyclines such as aklavin and aclacinomycin A, and 4-hydroxyanthracyclinones such as ɛ-rhodomycinone and aklavinone, were not substrates for the 4--methyltransferase. These reaction specificities indicate that glycosylation of the anthracyclinone molecule must occur before 4--methylation, which means that 4--methylation of carminomycin is probably the terminal step in the biosynthesis of daunomycin, and that daunomycinone is not an intermediate in the pathway.


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