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.

Synthesis of Novel Nucleo‐β‐Amino Acids and Nucleobase‐Functionalized β‐Peptides

“…These compounds should serve as versatile building blocks for PNA analogs, templates for 5Ј-methacryloylnucleoside polymerisation, [22] and biologically active agents. We incorporated these nucleo-β 3 -amino acids into water-soluble β-peptides.…”

Water soluble triblock and pentablock poly(methacryloyl nucleosides) from copper-mediated living radical polymerisation using PEG macroinitiators

“…The two polymers interact in solution, probably through a mixture of hydrogen bonding and stacking interactions. Further synthetic developments using the monomers herein, studies into template directed polymerisations [41,[45][46][47][48] and interactions with single and double stranded nucleic acids of nucleoside containing copolymers in aqueous solutions are the subject of ongoing work.…”

Synthesis and assembly behavior of nucleobase‐functionalized block copolymers

“…The polymerization was started by the addition of 0.75 mL of a stock solution containing 3 (190 mg, 0.088 mmol) in 1.0 mL of DMSO-d 6 . At 69% conversion, 1-phenyl-1-(trimethylsiloxy)ethylene (268 mg 1.39 mmol) was added.…”

“…Monomer 2 was polymerized at 35 8C according to the general procedure with 2 (530.0 mg, 2.03 mmol), CuCl (13.1 mg, 0.132 mmol), and bpy (43.8 mg, 0.280 mmol) in 5.20 mL of DMSO-d 6 . The polymerization was started by the addition of 0.7 mL of a stock solution containing 3 (390 mg, 0.181 mmol) in 2.0 mL of DMSO-d 6 .…”

“…6 Both monomers were polymerized via ATRP to two different average DPs in the range of 10-30. At the conversion at which the desired DP was reached, the polymers were end-capped by the quenching of the ATRP reaction with a 10-fold excess of 1-phenyl-1-(trimethylsiloxy)ethylene (Scheme 1).…”