Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. I. Glycosidation of various anthracyclinones by an aclacinomycin-negative mutant and biosynthesis of aclacinomycins from aklavinone.

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Abstract
An aclacinomycin-negative mutant strain KE303 which required aklavinone aglycone for the production of anthracycline antibiotics was derived from S. 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 glycosidated to the biologically active anthracyclines, when they were fed to the growing culture. 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 via aklavin and MA144 S1.