Synthesis of a Le(y) neoglycoconjugate and Le(y)-functionalized gold glyconanoparticles

摘要

The thiol functionalized Le(v) neoglycoconjugate 1 has been synthesized and used to prepare the Le(v)-functionalized gold glyconanoparticle 2. The synthesis of 1 has been carried out using a stepwise glycosylation strategy in which a suitably protected D-glucosamine derivative has been sequentially glycosylated at position 3 and then at position 4 with conveniently protected alpha-L-fucopyranosyl and beta-D-galactopyranosyl donors, respectively. The galactosylation step afforded the imidate 16 when the glycosyl acceptor contained a N-acetyglucosamine unit and the desired 4-O-galactopyranosyl derivative when the amino function protected as phthalimido group. The gold glyconanoparticle 2 has been prepared from 1 and has been characterized by NMR spectroscopy and transmission electron microscopy (TEM). (C) 2004 Elsevier Ltd. All rights reserved.