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  • Title: Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.
    Author: Peltier-Pain P, Marchillo K, Zhou M, Andes DR, Thorson JS.
    Journal: Org Lett; 2012 Oct 05; 14(19):5086-9. PubMed ID: 22984807.
    Abstract:
    A two-step strategy for disaccharide modulation using vancomycin as a model is reported. The strategy relies upon a glycosyltransferase-catalyzed 'reverse' reaction to enable the facile attachment of an alkoxyamine-bearing sugar to the vancomycin core. Neoglycosylation of the corresponding aglycon led to a novel set of vancomycin 1,6-disaccharide variants. While the in vitro antibacterial properties of corresponding vancomycin 1,6-disaccharide analogs were equipotent to the parent antibiotic, the chemoenzymatic method presented is expected to be broadly applicable.
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