Synthesis of Simple Multivalent β-D-GalNAc-(1→4)-β-D-Gal Oligomers as Probes for Investigating the Interactions ofP. AeruginosaPili with Multivalent Receptors

Five multivalent β-D-GalNAc-(1→4)-β-D-Gal oligomers were selected and synthesized as probes for investigating the adhesin-receptor interactions of P. aeruginosa pili with multivalent receptors. They were synthesized by the amide coupling reactions of 8-(N-2-aminoethyl)carboxamidooctyl 4-O-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-β-D-galactopyranoside (7) with EDTA dianhydride, EDTA, Kemp's triacid and adipic acid with EDC, DIC and DCC combined with HOBt as coupling reagents and by the reaction of per-O-acetylated 7 with 1,3,5-benzenetricarbonyl trichloride followed by de-O-acetylation. These resulting multivalent compounds contain flexible C9 spacer arms as linkers attached to either flexible hydrophilic moieties or rigid hydrophobic cores.