Jan 31, 2013

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

Journal of Natural Products
Maoquan ZhouJon S Thorson

Abstract

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.

  • References71
  • Citations31

Citations

Mentioned in this Paper

Molecular Dynamics
Molecular Stereochemistry
10-hydroxycamptothecin
Bacterial Proteins
Alvocidib
Indole Alkaloids
Glucosides
Daidzein
Flavones
Aromatics

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