Asymmetric Enzymatic Glycosylation of Mitoxantrone

Asymmetric Enzymatic Glycosylation of Mitoxantrone

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 ant...

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Veröffentlicht in:Organic letters 2011-05, Vol.13 (10), p.2786-2788
Hauptverfasser: Zhou, Maoquan, Thorson, Jon S
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Drug Screening Assays, Antitumor
Female
Glucosides - chemical synthesis
Glucosides - chemistry
Glucosides - pharmacology
Glucosyltransferases - metabolism
Glycosylation
Glycosyltransferases - metabolism
Humans
K562 Cells
Mitoxantrone - analogs & derivatives
Mitoxantrone - chemical synthesis
Mitoxantrone - chemistry
Mitoxantrone - pharmacology
Protein Engineering
Stereoisomerism
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Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200977u