Syntheses of poly(ester-amide-sulfide)s by radical polyadditions of diolefins with dithiols and oxidations and enzymatic degradation of the obtained polymers were examined. The diolefins were synthesized from optically active amino alcohols and 4-pentenoic acid. The radical polyadditions of the diolefins with dithiols were carried out in the presence of AIBN (3 mol %) in DMF to afford high molecular weight polymers. The sulfide group in the polymer was selectively oxidized to sulfoxide and sulfone groups according to the amount of H2O2 used. The poly(ester-amide-sulfide)s derived from alaninol were degraded by lipase Rhizopus arrhizus.