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Exploring and Exploiting the Reactivity of Glucuronic Acid Donors

de Jong, Ana-Rae, Hagen, Bas, van der Ark, Vincent, Overkleeft, Herman S., Codée, Jeroen D. C., Van der Marel, Gijsbert A.
Journal of organic chemistry 2012 v.77 no.1 pp. 108-125
Streptococcus pneumoniae, esters, glucuronic acid, glycosylation, moieties, organic chemistry, trisaccharides
The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic acid esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiodisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.