Synthesis of immunogenic oligosaccharide-protein conjugates from the lipopolysaccharide of Neisseria gonorrhoeae P9

Abstract

Oligosaccharide was isolated from the lipopolysaccharide of Neisseria gonorrhoeae P9 following partial acid hydrolysis. The exposed terminal keto-deoxyoctonic acid group of the oligosaccharide was convert into the reactive phenylisothiocyanato derivative by reaction with 2-(4-aminophenyl)-ethylamine followed by reduction with sodium cyanoborohydride and treatment with thiophosgene. This intermediate was used to prepare an oligosaccharide-protein conjugate with either bovine serum albumin or purified gonococcal pili. Immunisation of rabbits with protein conjugates produced antibodies reactive with both pure protein and intact lipopolysaccharide.