Probing the regiospecificity of enzyme-catalyzed steroid glycosylation

Maoquan Zhou; Yanpeng Hou; Adel Hamza; Chang Guo Zhan; Tim S. Bugni; Jon S. Thorson

doi:10.1021/ol3024924

Probing the regiospecificity of enzyme-catalyzed steroid glycosylation

Maoquan Zhou, Yanpeng Hou, Adel Hamza, Chang Guo Zhan, Tim S. Bugni, Jon S. Thorson

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

37 Scopus citations

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.

Original language	English
Pages (from-to)	5424-5427
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	21
DOIs	https://doi.org/10.1021/ol3024924
State	Published - Nov 2 2012

Funding

Funders	Funder number
National Center for Research Resources	S10RR008438

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3024924

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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.",

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AU - Zhou, Maoquan

AU - Hou, Yanpeng

AU - Hamza, Adel

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AU - Bugni, Tim S.

AU - Thorson, Jon S.

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AB - 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.

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Probing the regiospecificity of enzyme-catalyzed steroid glycosylation

Abstract

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