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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'-?-D-glucoside are described.

SUBMITTER: Zhou M

PROVIDER: S-EPMC3099400 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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Asymmetric enzymatic glycosylation of mitoxantrone.

Zhou Maoquan M Thorson Jon S JS

Organic letters 20110429 10

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. ...[more]

PMID: 21528870

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