Biologically Active Branched Polysaccharide Mimetics: Synthesis via Ring-Opening Polymerization of a Maltose-Based ß-Lactam.

Stereoregular poly-amido-saccharides bearing α-glucopyranose branches (Mal-PASs) are synthesized by anionic ring-opening polymerization of a maltose-based ß-lactam monomer followed by debenzylation. The polymerization affords high molecular weight polymers (up to 31500 g/mol) with narrow dispersities (D < 1.1). Deprotected Mal-PASs are highly soluble in water and adopt a left-handed helical conformation in solution. Turbidimetric assay shows that Mal-PASs are multivalent ligands to lectin Concanavalin A.