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 journalArticlepeer-review

34 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 languageEnglish
Pages (from-to)5424-5427
Number of pages4
JournalOrganic Letters
Volume14
Issue number21
DOIs
StatePublished - Nov 2 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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