Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. I. Glycosidation of various anthracyclinones by an aclacinomycin-negative mutant and biosynthesis of aclacinomycins from aklavinone.
An aclacinomycin-negative mutant strain KE303 which required aklavinone aglycone for the production of anthracycline antibiotics was derived from Streptomyces galilaeus, and employed for the glycosidation of various anthracyclinones. epsilon- gamma- and beta-Rhodomycinones, epsilon-isorhodomycinone, epsilon- and beta-pyrromycinones and chemically modified aklavinones were found to be glycosidated to the biologically active anthracyclines, when they were fed to the growing culture. However, the feeding of daunomycinone, 13-deoxydaunomycinone, adriamycinone and steffimycinone did not yield any glycoside. The bioconversion of presumptive precursor glycosides revealed that aclacinomycin A is biosynthesized by the step-wise glycosidation from aklavinone vai aklavin and MA144 S1.
D015250:Aclarubicin / Q000031:analogs & derivatives*; D000903:Antibiotics, Antineoplastic; D055598:Chemical Phenomena; D002621:Chemistry; D006027:Glycosides / Q000378:metabolism; D009154:Mutation; D009279:Naphthacenes / Q000096:biosynthesis* / Q000378:metabolism*; D013302:Streptomyces / Q000378:metabolism*
D000903:Antibiotics, Antineoplastic; D006027:Glycosides; D009279:Naphthacenes; C011157:aclacinomycins; C027832:aklavinone; D015250:Aclarubicin