A facile and efficient enzymatic and polymerization process was used to prepare polymeric prodrugs of ketoprofen with saccharide side chains. The chains included branches that included glucose, mannose, galactose, and lactose, and these were synthesized through free radical reaction. The prodrugs were characterized by FT-IR, NMR, and GPC and drug-loading capacity was influenced by varying the ratios of initiator and monomers (range 32.13 and 68.56% w/w). In vitro release characteristics of the polymeric drugs were systematically evaluated over the pH range 1.2-8.0 and the release profiles indicated that the hydrolytic nature of polymers were strongly depended on the variation in saccharide content, carbon chain length, and pH. The outcomes from this study demonstrate the importance of carbohydrate structures and how these are linked to drug release.