Synthesis and immunoreactivity of poly(acrylamide) copolymers containing C-3- and C-7-modified, carboxyl-reduced, 4-O- and 5-O-phosphorylated Kdo residues

Article abstract of DOI:10.1016/0008-6215(93)87007-F

Sodium (allyl 3-deoxy-α-D-lyxo-2-heptulopyranosid)onate (6), allyl 3-deoxy-β- and -α-D-manno-2-octulopyranoside, sodium (allyl 3-deoxy-β-L-gulo-2-octulopyranosid)onate, sodium (allyl α-D-glycero-D-talo-2-octulopyranosid)onate, sodium (allyl α-D-glycero-D-galacto-2-octulopyranosidonate, ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-α-D-manno-2-octulopyranosid)onate, and ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-β-D-manno-2-octulopyranosid)onate were prepared and copolymerized with acrylamide to give multivalent haptens, which were used in immune inhibition assays. The monoclonal antibody A 20, directed against α-pyranoside Kdo residues, did not react with these compounds, except with heptulosonic acid derivative 6, thus proving that the terminal hydroxymethyl group of Kdo is not required for binding. Sodium (allyl 3-deoxy-α-D-(yxo-2-heptulopyranosid)onate (6), allyl 3-deoxy-β- and -α-D-manno-2-octulopyranoside, sodium (allyl 3-deoxy-β-L-gulo-2-octulopyranosid)onate, sodium (allyl α-D-glycero-D-talo-2-octulopyranosid)onate, sodium (allyl α-D-glycero-D-galacto-2-octolopyranosidonate, ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-α-D-manno-2-octulopyranosid)onate, and ammonium (allyl 3-deoxy-4-O- and -5-O-phosphono-β-D-manno-2-octulopyranosid)onate were prepared and copolymerized with acrylamide to give multivalent haptens, which were used in immune inhibition assays. The monoclonal antibody A 20, directed against α-pyranoside Kdo residues, did not react with these compounds, except with heptulosonic acid derivative 6, thus proving that the terminal hydroxymethyl group of Kdo is not required for binding.