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Probing the Regiospecificity of Enzyme-Catalyzed Steroid Glycosylation

Author:
Zhou, Maoquan, Hou, Yanpeng, Hamza, Adel, Zhan, Chang-Guo, Bugni, Tim S., Thorson, Jon S.
Source:
Organic letters 2012 v.14 no.21 pp. 5424-5427
ISSN:
1523-7052
Subject:
bufadienolides, catalysts, chemical structure, digoxigenin, glucosylation, regioselectivity
Abstract:
The potential of a uniquely permissive engineered glycosyltransferase (OleD ASP) as a catalyst for steroid glycosylation is highlighted. The ability of OleD ASP to glucosylate a range of cardenolides and bufadienolides was assessed using a rapid LC-UV/MS-SPE-NMR analytical platform. While a bias toward OleD-catalyzed C3 monoglucosylation was observed, subtle alterations of the steroidal architecture, in some cases, invoked diglucosylation or, in one case (digoxigenin), C12 glucosylation. This latter case represents the first, and highly efficient, synthesis of digoxigenin 12-O-β-d-glucoside.
Agid:
5784584