Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation

P Peltier-Pain, K Marchillo, M Zhou, DR Andes…

Index: Peltier-Pain, Pauline; Marchillo, Karen; Zhou, Maoquan; Andes, David R.; Thorson, Jon S. Organic Letters, 2012 , vol. 14, # 19 p. 5086 - 5089

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Citation Number: 21

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 ...