Synthesis of a novel structural triblock copolymer of poly(gamma -benzyl-l-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone)

Biomaterials. 2004 Aug;25(17):3553-8. doi: 10.1016/j.biomaterials.2003.10.018.

Abstract

A novel structural triblock copolymer of poly(gamma-benzyl-l-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone) (PBLG-PEO-PCL) was synthesized by a new approach in the following three steps: (1) sequential anionic ring opening polymerization (ROP) of ethylene oxide and epsilon-caprolactone with an acetonitrile/potassium naphthalene initiator system to obtain a diblock copolymer CN-PEO-PCL with a cyano end-group; (2) conversion of the CN end-group into NH2 end-group by hydrogenation to obtain NH2-PEO-PCL; (3) ROP of gamma-benzyl-l-glutamate-N-carboxyanhydrides (Bz-l-GluNCA) with NH2-PEO-PCL as macroinitiator to obtain the target triblock copolymer. The structures from CN-PEO precursor to the triblock copolymers were confirmed by FT-IR and 1H NMR spectroscopy, and their molecular weights were measured by gel permeation chromatography. The monomer of Bz-l-GluNCA can react almost quantitatively with the amino end-groups of NH2-PEO-PCL macroinitiator by ROP.

Publication types

  • Comparative Study
  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry*
  • Lactones / chemical synthesis
  • Lactones / chemistry*
  • Materials Testing
  • Molecular Conformation
  • Molecular Weight
  • Polyethylenes / chemical synthesis
  • Polyethylenes / chemistry*
  • Polyglutamic Acid / analogs & derivatives*
  • Polyglutamic Acid / chemical synthesis
  • Polyglutamic Acid / chemistry*

Substances

  • Biocompatible Materials
  • Lactones
  • Polyethylenes
  • poly(gamma-benzyl-l-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone)
  • Polyglutamic Acid