Syntheses of novel sulfated glycans for cell-adhesion interaction studies

Stereoselective syntheses of two 3-O-Gal sulfated trisaccharides GalNAc(1-4)[(3-SE)-Gal](1-3)GalNAc-O-All and GalNAc(1-4)[(3-SE)-Gal](1-4)Glc-O- All were accomplished through the use of three novel glycosyl acceptors, namely, allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino) - d-galactopyranoside, methyl 2,6-di-O-benzoyl-3-O-naphthylmethyl - d-galactopyranoside and allyl 6-O-acetyl-2-O-benzoyl-3-O-naphthylmethyl - d-galactopyranosyl-(14)-2,3,6-tri-O-benzoyl - d-glucopyranoside. These sulfated trisaccharides were expected to act as potential reference compounds for human 4GalNAc transferase and can be effectively used as antigens when linked to KLH.