Controlled radical polymerization of an acrylamide containing l-alanine moiety via ATRP

Abstract

Homopolymerization of an optically active acrylamide having an amino acid moiety in the side chain, N-acryloyl-l-alanine (AAla) was carried out via atom transfer radical polymerization (ATRP) at room temperature using 2-hydroxyethyl-2′-methyl-2′-bromopropionate (HMB) or sodium-4-(bromomethyl)benzoate (SBB) as initiator in pure water, methanol/water mixture and pure methanol solvents. The polymerization reaction resulted in the optically active biocompatible amino acid-based homopolymer in good yield with narrow molecular weight distribution. The number average molecular weight increased with conversion and polydispersity was low. The structure and molecular weight of synthesized polymer were characterized by ¹H NMR, FT-IR spectroscopic techniques and size-exclusion chromatography.