Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of glycosphingolipids from the parasite Schistosoma mansoni.

Synthetic access to three neutral glycosphingolipids from the parasite Schistosoma mansoni adult worm has been achieved. These structures differ significantly from those of other parasites and exhibit a unique structural motif termed "schisto-core" consisting of GalNAcbeta1-->4Glcbeta1-->sequence. We have synthesized glycosphingolipids, beta-D-GalNAcp-(1-->4)-beta-D-Glcp-(1-->1)Cer (1), beta-D-GlcNAcp-(1-->3)-beta-D-GalNAcp-(1-->4)-beta-D-Glcp-(1-->1)Cer (2) and beta-D-Galp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-GalNAcp-(1-->4)-beta-D-Glcp-(1-->1)Cer (3).