title: Synthesis of polypeptide block copolymer hybrids by the combination of N-carboxyanhydride polymerization and RAFT.
abstract: The synthesis of hybrid bioconjugates via the ring-opening polymerization (ROP) of N-carboxyanhydrides (NCAs) using a synthetic macroinitiator is described. Poly(n-butyl acrylate), polystyrene, and poly(N-isopropyl acrylamide) are synthesized (polydisperity index, Đ < 1.1) using reversible addition-fragmentation chain transfer (RAFT) as the synthetic tool. A phthalimidomethyl trithiocarbonate RAFT chain transfer agent is used to prepare well-defined, end-functional polymers, which after deprotection result in amine terminal macroinitiators. The subsequent initiating systems could successfully be chain extended with ε-benzyloxycarbonyl-l-lysine or γ-benzyl-l-glutamate as the NCAs to produce a library of polymer-polypeptide conjugates. In doing so, a novel procedure for directly synthesizing bioconjugates via a non-modular route without the need for excessive purification and isolation steps is described.
authors.affiliation: Dublin City University, School of Chemical Sciences, Glasnevin, Dublin 9, Ireland.
authors.forename: Jaco
authors.initials: J
authors.lastname: Jacobs
authors.forename: Nicholas
authors.initials: N
authors.lastname: Gathergood
authors.forename: Andreas
authors.initials: A
authors.lastname: Heise
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000180:Acrylic Resins / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*; D011137:Polystyrenes / Q000737:chemistry*
chemical_list: D000179:Acrylates; D000180:Acrylic Resins; D000812:Anhydrides; D010455:Peptides; D011108:Polymers; D011137:Polystyrenes; C498324:poly(n-butyl acrylate); C052970:poly-N-isopropylacrylamide
keywords: N-carboxyanhydride (NCA) polymerization; block copolymers; polypeptides; reversible addition fragmentation chain transfer (RAFT)