Assessing the Regioselectivity of OleD-Catalyzed Glycosylation with a Diverse Set of Acceptors

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• 作者：Maoquan Zhou ; Adel Hamza ; Chang-Guo Zhan ; Jon S. Thorson
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：February 22, 2013
• 年：2013
• 卷：76
• 期：2
• 页码：279-286
• 全文大小：439K
• 年卷期：v.76,no.2(February 22, 2013)
• ISSN：1520-6025

文摘

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavones鈥?(daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2-methoxyestradiol)鈥攚ere 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.