The synthesis of the amphiphilic homoglycopolypeptide was carried out by a combination of NCA polymerization and click chemistry to yield a well-defined polypeptide having an amphiphilic carbohydrate on its side chain. The amphiphilicity of the carbohydrate was achieved by incorporation of an alkyl chain at the C-6 position of the carbohydrate thus also rendering the homoglycopolypeptide amphiphilic. The homoglycopolypeptide formed multimicellar aggregates in water above a critical concentration of 0.9 μM due to phase separation. The multimicellar aggregates were characterized by DLS, TEM, and AFM. It is proposed that hydrophobic interactions of the aliphatic chains at the 6-position of the sugar moieties drives the assembly of these rod-like homoglycopolypeptide into large spherical aggregates. These multimicellar aggregates encapsulate both hydrophilic as well as hydrophobic dye as was confirmed by confocal microscopy. Finally, amphiphilic random polypeptides containing 10% and 20% α-d-mannose in addition to glucose containing a hydrophobic alkyl chain at its 6 position were synthesized by our methodology, and these polymers were also found to assemble into spherical nanostructures. The spherical assemblies of amphiphilic random glycopolypeptides containing 10% and 20% mannose were found to be surface bioactive and were found to interact with the lectin Con-A.