title: Anthracycline metabolites of tetracenomycin C-nonproducing Streptomyces glaucescens mutants.
abstract: Mutants of Streptomyces glaucescens GLA.0 which are blocked in the production of tetracenomycin C (compound 1), an anthracycline antibiotic having significant antitumor activity, accumulated several new anthracycline metabolites structurally related to compound 1 and to intermediates of its biosynthetic pathway. Through chemical and spectroscopic comparisons with the known anthracycline metabolites of the wild-type strain, we identified the two regioisomers of tetracenomycin B2 (compounds 7a and 7b), 8-demethyltetracenomycin C (compound 12), tetracenomycin D2 (compound 11), tetracenomycin E (compound 13), and the 12-naphthacenone forms of compounds 7a, 7b, and 2 (tetracenomycin D1). A hypothetical biosynthetic pathway to compound 1 is presented that is consistent with the occurrence of compounds 7b, 13, and 5 (tetracenomycin A2) and with the cosynthetic behavior of tetracenomycin C-nonproducing mutants (H. Motamedi, E. Wendt-Pienkowski, and C. R. Hutchinson, J. Bacteriol. 167:575-580, 1986).
authors.forename: S
authors.initials: S
authors.lastname: Yue
authors.forename: H
authors.initials: H
authors.lastname: Motamedi
authors.forename: E
authors.initials: E
authors.lastname: Wendt-Pienkowski
authors.forename: C R
authors.initials: CR
authors.lastname: Hutchinson
mesh_terms: D000903:Antibiotics, Antineoplastic; D009154:Mutation; D009279:Naphthacenes / Q000096:biosynthesis / Q000378:metabolism; D013302:Streptomyces / Q000235:genetics / Q000378:metabolism*
chemical_list: D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes; C020938:tetracenomycin C