title: Triple hydroxylation of tetracenomycin A2 to tetracenomycin C involving two molecules of O(2) and one molecule of H(2)O.
abstract: The TcmG or ElmG oxygenase-catalyzed triple hydroxylation of tetracenomycin (Tcm) A2 to Tcm C proceeds via a novel monooxygenase-dioxygenase mechanism, deriving the 4- and 12a-OH groups of Tcm C from two molecules of O(2) and the 4a-OH group of Tcm C from a molecule of H(2)O. These results suggest a mechanistic analogy among TcmG, ElmG, and the bacterial and fungal hydroquinone epoxidizing dioxygenases, as well as the mammalian vitamin K-dependent gamma-glutamyl carboxylase.
authors.affiliation: Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, USA.
authors.forename: E R
authors.initials: ER
authors.lastname: Rafanan
authors.forename: C R
authors.initials: CR
authors.lastname: Hutchinson
authors.forename: B
authors.initials: B
authors.lastname: Shen
mesh_terms: D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005800:Genes, Fungal; D006900:Hydroxylation; D009279:Naphthacenes / Q000138:chemical synthesis / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010105:Oxygenases / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry / Q000235:genetics; D014867:Water / Q000737:chemistry
chemical_list: D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes; D014867:Water; C020938:tetracenomycin C; C090681:tetracenomycin A2; D010105:Oxygenases; D010100:Oxygen