Synthesis of semitelechelic maleimide poly(PEGA) for protein conjugation by RAFT polymerization

Biomacromolecules. 2009 Jul 13;10(7):1777-81. doi: 10.1021/bm9001987. Epub 2009 Jun 9.

Abstract

Maleimide end functionalized polymers for site-selective conjugation to free cysteines of proteins were synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization. A furan-protected maleimide chain transfer agent (CTA) was employed in the RAFT polymerization of poly(ethylene glycol) methyl ether acrylate (PEGA). Gel permeation chromatography (GPC) with laser light scattering detection indicated that 20,000 and 39,000 Da polyPEGA had been made with polydispersity indices of 1.25 and 1.36, respectively. The maleimide group on the polymer chain end was exposed by heating the poly(PEGA)s for 4 h. The deprotection efficiency was estimated to be 80 and 60% for poly(PEGA)(20 kDa) and poly(PEGA)(39 kDa), respectively. Maleimide-poly(PEGA)s were conjugated to V131C T4 lysozyme (T4L), and the resultant polymer-protein conjugates were characterized by size exclusion chromatography and gel electrophoresis.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Chromatography, Gel
  • Cysteine
  • Electrophoresis, Polyacrylamide Gel
  • Maleimides / chemistry*
  • Molecular Weight
  • Muramidase / chemistry
  • Polyethylene Glycols / chemical synthesis*
  • Polymerization*
  • Proteins / chemistry*

Substances

  • Maleimides
  • Proteins
  • bis(polyoxyethylene bis(amine))
  • maleimide
  • Polyethylene Glycols
  • Muramidase
  • Cysteine