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Updated: Feb 3, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
PEG Analogs Synthesized by Ring-Opening Metathesis Polymerization for Reversible Bioconjugation
Emma M Pelegri-O'Day1, Nicholas M Matsumoto1, Kyle Tamshen1
1Department of Chemistry and Biochemistry and California Nanosystems Institute , University of California, Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States.
Abstract:
Poly(ethylene glycols) (PEGs) with protein-reactive end-groups are widely utilized in bioconjugation reactions. Herein, we describe the use of ring-opening metathesis polymerization (ROMP) to synthesize unsaturated protein-reactive PEG analogs. These ROMP PEGs (rPEGs) contained terminal aldehyde functionality and ranged in molecular weight from 6 to 20 kDa. The polymers were readily conjugated to free amines on the protein hen egg-white lysozyme (Lyz). Biocompatibility of the unsaturated PEGs was assessed in vitro, revealing the polymers to be nontoxic up to concentrations of at least 1 mg/mL in human dermal fibroblasts (HDFs). The resulting unsaturated rPEG-lysozyme conjugates underwent metathesis-based depolymerization, resulting in decreased molecular weight of the conjugate.
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