SYNTHESIS OF O-BETA-D-GALACTOPYRANOSYL-(1-3)-O-BETA-D-GALACTOPYRANOSYL-(1-4)-O-BETA-D-XYLOPYRANOSYL-(1-3)-L-SERINE (GAL-GAL-XYL-SER)

O-β-D-Galactopyranoayl-(1—>3)-O-β-D-galactopyranosyl-(1—>4)-O-β-D-xylopyranosyl-(1—>3)-L-serine (Gal-Gal-Xyl-Ser) was prepared by a procedure involving the synthesis of a benzoylated galactobiosyl bromide and a xylosylserine derivative with an unsubstituted hydroxyl group at C-4 (3-0-(2, 3-di-O-benzoyl-β-D-xylopyranosyl)-N-carbobenzoxy-L-serine benzyl ester), followed by condensation and deblocking. The structure of the product was confirmed by 1H-and 13C-NMR spectroscopy. Upon incubation with an extract of embryonic chick cartilage, the synthetic Gal-Gal-Xyl-Ser served as an acceptor for enzymatic glucuronosyl transfer from UDP-D-glucuronic acid. © 1990, Taylor & Francis Group, LLC. All rights reserved.