A copolymer from N‐isopropylacryl amide (NIPAAm) and N‐homocysteine thiolactone acrylamide (TlaAm), prepared by RAFT polymerization, is reacted with various amines, bearing alkyl residues of increasing length (n‐propylamine, n‐hexylamine, and n‐dodecylamine) to liberate the corresponding thiol, which is consequently reacted in situ with 2‐bromoethyl‐2′,3′,4′,6′‐tetra‐O‐acetyl‐α‐d ‐mannopyranoside. The resulting double‐modified graft copolymers show characteristic self‐assembly behavior due to their amphiphilic nature, affording glycopolymer‐based nanoparticles. While the n‐propylamine‐derived amphiphiles mainly lead to micelles (30 nm), the n‐hexylamine adducts give rise to larger vesicles (200–600 nm). Longer alkyl amines result in the formation of large compound micelles. The assembled nanoparticles are bioactive and interact effectively with Concanavalin A (ConA).
