Rational design and synthesis of peptide ligands for an anti-carbohydrate antibody and their immunochemical characterization.

Molecular mimics of carbohydrates present an alternative source of compounds to target pathways involving protein-carbohydrate interactions. Certain peptides act as molecular mimics of carbohydrates in binding to anti-carbohydrate antibodies. A series of potential peptide ligands for the anti-carbohydrate antibody SYA/J6, directed against Shigella flexneri Y, was designed by molecular modeling based on a crystal structure of the antibody complex with a carbohydrate-mimetic peptide. These octapeptides were synthesized using solid-phase peptide synthesis, and their recognition by the antibody was investigated. The results shed light on the nature of peptide-carbohydrate mimicry.