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J Nat Prod. 2013 Feb 22;76(2):279-86. doi: 10.1021/np300890h. Epub 2013 Jan 29.

Assessing the regioselectivity of OleD-catalyzed glycosylation with a diverse set of acceptors.

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1
Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin, Madison, WI 53705, United States.

Abstract

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavones- (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2-methoxyestradiol)-were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.

PMID:
23360118
PMCID:
PMC3607945
DOI:
10.1021/np300890h
[Indexed for MEDLINE]
Free PMC Article
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