Synthesis of diols containing nucleic acid bases and their polyesters

Abstract

AbstractPreparation of four diols containing nucleic acid bases derived from 3‐(thymin‐1‐yl)propanoic acid (3‐TPA) and 3‐(uracil‐1‐yl)propanoic acid (3‐UPA), and the corresponding model polymers of polynucleotides with linear polyester backbone and nucleic acid base derivative as pendant side chains are described. N‐(1′,3′‐Dihydroxy‐2′‐methyl‐2′‐propyl)‐3‐(thymin‐1‐yl)propionamide (VIa, 3‐HMPTPA), N‐(1′3′‐dihydroxy‐2′‐methyl‐2′‐propyl)‐3‐(uracyl‐1‐yl)propionamide (VIb, 3‐HMPUPA) and their isomers, N(β,β‐dihydroxyethyl)‐3‐(thymin‐1‐yl)propionamide (VIIa, 3‐HETPA), and N‐(β,β‐dihydroxyethyl)‐3‐(uracil‐1‐yl)propionamide (VIIb, 3‐HEUPA) were synthesized through the selective N‐acylation of 2‐methyl‐2‐amino‐1,3‐propanediol and diethanolamine with 3‐TPA and 3‐UPA, respectively, by the active ester‐N‐hydroxyl‐1,4‐epoxy‐5‐cyclohexene‐2,3‐dicarboximide (HOEC) method. The resulting diols were polycondensed with active diamide of benzotriazole (HBT) such as 1,1′‐(isophthaloyl)bis‐benzotriazole (IPBBT), giving polyesters containing thymine and uracil derivatives as the side group, by the selective O‐acrylation of active amide‐benzotriazole method.