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

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


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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bacterial Proteins / metabolism*
  • Catalysis
  • Glucosides / chemistry*
  • Glucosyltransferases / metabolism*
  • Glycosylation
  • Isoflavones / chemistry*
  • Resveratrol
  • Stereoisomerism
  • Stilbenes / chemistry
  • Streptomyces antibioticus / enzymology*


  • Bacterial Proteins
  • Glucosides
  • Isoflavones
  • Stilbenes
  • daidzein
  • Glucosyltransferases
  • OleD protein, Streptomyces antibioticus
  • Resveratrol