Synthesis and Anaphylactogenicity of Monohaptenic Carbohydrate Conjugates

Peptidic model conjugates carrying a single 2‐carboxy‐4,6‐dinitrophenyl haptenic group, and as carbohydrate moieties D ‐gluconoyl, β‐ D ‐mannopyranosyl, 2‐deoxy‐β‐ D ‐glucopyranos‐2‐yl, or lactobionoyl residues, including the pseudocarbohydrate residue 1,3,4,5‐tetrahydroxycyclohexane‐1‐carbonyl, were synthesized. Conjugates carrying the lactobionoyl of the bis(2‐deoxy‐β‐ D ‐glucopyranos‐2‐yl) moiety were anaphylactogenic in the guinea pig, passively sensitized against 2‐carboxy‐4,6‐dinitrophenyl antigen.