All-transglycolytic synthesis and characterization of sialyl(α2-3)galactosyl(β1-4)xylosyl-p-nitrophenyl(β1-, an oligosaccharide derivative related to glycosaminoglycan biosynthesis

Abstract

β-D-Xylopyranosides, such as p-nitrophenyl-β-D-xylopyranoside (Xyl-Np) or 4-methylumbelliferyl-β-D-xylopyranoside (Xyl-MeUmb), when added to the culture medium of human skin fibroblasts have previously been shown to produce some Np- or MeUmb-oligosaccharides related to the regulation of glycosaminoglycan biosynthesis. Among these oligosaccharide derivatives, we synthesized the trisaccharide derivative NeuAc(α2-3)Gal(β1-4)Xyl-Np(β1- as a potential inhibitor of human skin fibroblast glycosaminoglycan biosynthesis. This synthesis was achieved by sequential use of transglycosylating activities of Escherichia coli β-galactosidase and Trypanosoma cruzi trans-sialidase. The structure of the oligosaccharide obtained was determined by HPLC, ion-spray mass spectrometry, and NMR.