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Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.


ABSTRACT: An efficient method to synthesize telechelic, bio-reactive polymers is described. Homotelechelic polymers were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization in one step by employing bifunctional chain transfer agents (CTAs). A bis-carboxylic acid CTA was coupled to N-BOC-aminooxy ethanol or pyridyl disulfide ethanol resulting in a bis-N-BOC-aminooxy CTA and a bis-pyridyl disulfide CTA, respectively. RAFT polymerization of polyethylene glycol (PEG) acrylate in the presence of both CTAs resulted in a series of polymers over a range of molecular weights (~8.4 kDa to 35.2 kDa; polydispersity indices, PDIs of 1.11 to 1.44) with retention of end-groups post-polymerization. The polymers were characterized by (1)H NMR spectroscopy and gel permeation chromatography (GPC). Conjugations of small molecules and peptides resulted in homotelechelic polymer conjugates.

SUBMITTER: Grover GN 

PROVIDER: S-EPMC3956054 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.

Grover Gregory N GN   Lee Juneyoung J   Matsumoto Nicholas M NM   Maynard Heather D HD  

Macromolecules 20120601 12


An efficient method to synthesize telechelic, bio-reactive polymers is described. Homotelechelic polymers were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization in one step by employing bifunctional chain transfer agents (CTAs). A bis-carboxylic acid CTA was coupled to <i>N</i>-BOC-aminooxy ethanol or pyridyl disulfide ethanol resulting in a bis-<i>N</i>-BOC-aminooxy CTA and a bis-pyridyl disulfide CTA, respectively. RAFT polymerization of polyethylene glycol  ...[more]

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