Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-gluco pyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oli gosaccharide fragment of the aggregation factor of the marine sponge Microc iona prolifera. The title compound was obtained by coupling of 3-O-allyloxy carbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl t richloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, foll owed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfa tion, de-acylation, and finally N-acetylation. The allyl glycoside was even tually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupl ed to bovine serum albumin (BSA) using diethyl squarate as the bivalent lin ker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Sci ence Ltd. All rights reserved.