Synthesis of a set of sulfated and/or phosphorylated oligosaccharide derivatives from the carbohydrate-protein linkage region of proteoglycans.
The synthesis of a set of various sulfoforms and/or phosphoforms as 7-methoxy-2-naphthyl glycosides of beta-D-Xylp, beta-D-Galp-(1-->4)-beta-D-Xylp, and beta-D-Galp-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Xylp, structures encountered in the common carbohydrate-protein linkage region of proteoglycans, is reported for the first time. These molecules will serve as probes for systematic studies of the substrate specificity of the glycosyltransferases involved in the early steps of the biosynthesis of proteoglycans. A straightforward divergent preparation was achieved using key intermediates, which were designed as common precursors.
Jacquinet
Jean-Claude
JC
Institut de Chimie Organique et Analytique, UMR CNRS 6005, UFR Faculté des Sciences, Université d'Orléans, BP 6759, F-45067 Orléans Cedex, France. Jean-Claude.Jacquinet@univ-orleans.fr
D002240:Carbohydrate Sequence; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010755:Organophosphates / Q000138:chemical synthesis*; D011509:Proteoglycans / Q000737:chemistry*; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*
D009844:Oligosaccharides; D010755:Organophosphates; D011509:Proteoglycans; D013463:Sulfuric Acid Esters