Hydrogen Bond Template-Directed Polymerization of Protected 5‘-Acryloylnucleosides

Abstract

Poly(5‘-acryloyluridine) has been shown to act as a template in the radical polymerization of the complementary 5‘-acryloyladenosine in the presence of the noncomplementary 5‘-acryloyluridine. The template was synthesized by polymerizing 5‘-acryloyluridine using AIBN as the initiator. The 5‘-acryloylnucleosides were synthesized by regiospecific acylation of adenosine and uridine at the 5‘-position using the enzyme Candida antarctica lipase 435 (CAL 435). The remaining hydroxyl groups were protected as silyl ethers to increase the solubility in nonpolar solvents.