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-DGalp-(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. (c) 2006 Elsevier Ltd. All rights reserved.