Synthesis of phosphorylated 3,4-branched trisaccharides corresponding to LPS inner core structures of Neisseria meningitidis and Haemophilus influenzae

Abstract

2-( N-Benzyloxycarbonyl)aminoethyl 7- O-acetyl-6- O-allyl-2- O-benzoyl-4- O-benzyl-3- O-chloroacetyl- l- glycero-α- d- manno-heptopyranosyl-(1→3)-[2,3,4,6-tetra- O-benzoyl-β- d-glucopyranosyl-(1→4)]-6,7-di- O-acetyl-2- O-benzyl- l- glycero-α- d- manno-heptopyranoside, a spacer-equipped protected derivative of the common 3,4-branched diheptoside trisaccharide structure of the lipopolysaccharide core of Neisseria meningitidis and Haemophilus influenzae has been synthesized. The protecting group pattern installed allows regioselective introduction of phosphoethanolamine residues in the 3- and 6-position of the second heptose unit in accordance with native structures. From this intermediate the 3-and 6-monophosphoethanolamine as well as the non-phosphorylated deprotected trisaccharides have been synthesized to be used in evaluation of antibody binding specificity and in investigation of the substrate specificity of glycosyl transferases involved in the biosynthesis of LPS core structures.