title: Asymmetric enzymatic glycosylation of mitoxantrone.
abstract: Using a uniquely promiscuous engineered glycosyltransferase (GT) derived from the macrolide-inactivating GT OleD, a single-step asymmetric glucosylation of one 'arm' of the drug mitoxantrone was efficiently achieved in high stereo- and regiospecificity. The synthesis, structural elucidation, and anticancer activity of the corresponding mitoxantrone 4'-β-D-glucoside are described.
authors.affiliation: Pharmaceutical Sciences Division, School of Pharmacy, Wisconsin Center for Natural Products Research, University of Wisconsin-Madison, Madison, Wisconsin 53705, United States.
authors.forename: Maoquan
authors.initials: M
authors.lastname: Zhou
authors.forename: Jon S
authors.initials: JS
authors.lastname: Thorson
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005964:Glucosyltransferases / Q000378:metabolism; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism*; D006801:Humans; D020014:K562 Cells; D008942:Mitoxantrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015202:Protein Engineering; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D005960:Glucosides; C559564:mitoxantrone 4'-beta-D-glucoside; D008942:Mitoxantrone; D016695:Glycosyltransferases; D005964:Glucosyltransferases; C075034:macrolide glycosyltransferase