title: Exploring and exploiting the reactivity of glucuronic acid donors.
abstract: 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.
authors: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors: Ana-Rae
authors: AR
authors: de Jong
authors: Bas
authors: B
authors: Hagen
authors: Vincent
authors: V
authors: van der Ark
authors: Herman S
authors: HS
authors: Overkleeft
authors: Jeroen D C
authors: JD
authors: Codée
authors: Gijsbert A
authors: GA
authors: Van der Marel
mesh_terms: D020723:Glucuronic Acid / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D014312:Trisaccharides; D020723:Glucuronic Acid