Asymmetric enzymatic glycosylation of mitoxantrone

Maoquan Zhou; Jon S. Thorson

doi:10.1021/ol200977u

Asymmetric enzymatic glycosylation of mitoxantrone

Maoquan Zhou, Jon S. Thorson

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

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.

Original language	English
Pages (from-to)	2786-2788
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	10
DOIs	https://doi.org/10.1021/ol200977u
State	Published - May 20 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200977u

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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.",

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T1 - Asymmetric enzymatic glycosylation of mitoxantrone

AU - Zhou, Maoquan

AU - Thorson, Jon S.

PY - 2011/5/20

Y1 - 2011/5/20

N2 - 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.

AB - 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.

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U2 - 10.1021/ol200977u

DO - 10.1021/ol200977u

M3 - Article

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AN - SCOPUS:79956071467

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VL - 13

SP - 2786

EP - 2788

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Asymmetric enzymatic glycosylation of mitoxantrone

Abstract

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