Glycopolypeptide conformations in bioactive block copolymer assemblies influence their nanoscale morphology

We describe the preparation and assembly of glycosylated amphiphilic diblock copolypeptides, where the hydrophilic glycosylated segments adopt either alpha -helical or disordered conformations. In this study, glycosylated amphiphilic diblock copolypeptides were prepared using poly(l-leucine), poly(L), as the hydrophobic segment, and poly( alpha -d-galactopyranosyl-l-lysine), poly( alpha -gal-K), or poly( alpha -d-galactopyranosyl-l-cysteine sulfone), poly( alpha -gal-C super(O2)), as the hydrophilic segment. The poly( alpha -gal-K) and poly( alpha -gal-C super(O2)) segments are known to be fully alpha -helical (>90% at 20 degree C) and fully disordered in water, respectively. We found that block copolypeptides containing galactosylated hydrophilic segments of either alpha -helical or disordered conformation give different assembly morphologies, where the disordered glycopolypeptide segments favor vesicle formation and also present sugar residues that can bind to biological targets.